22
OE?A?INUeEA OA?IAOeAAOE*IA AEAAeAI?ss
wmetafile8? ?????Z????????&??yyyy????MrEd?Microsoft
Draw??Z???&?©?MrEd?????
?AO?O??AA Ieueaa Aiaoie??aia
OAeE 547.831.7/8:54.04:54.057
NEIOAC, O?CEEI-O?I?*I? OA A?IEIA?*I? AEANOEAINO? 3-CAI?UAIEO
4-A?Ae?IENE-2-IENI-O?IIE?I?A
15.00.02 – oa?iaoeaaoe/ia o?i?y ? oa?iaeiaiic?y
AAOI?AOA?AO
aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy
eaiaeeaeaoa oa?iaoeaaoe/ieo iaoe
Oa?e?a – 1999
Aeena?oaoe??th ? ?oeiien.
?iaioa aeeiiaia ia eaoaae?? oa?iaoeaaoe/ii? o?i?? Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai??, I?i?noa?noai ioi?iie caei?ia’y Oe?a?ie.
Iaoeiaee ea??aiee: eaiaeeaeao oa?iaoeaaoe/ieo iaoe, aeioeaio
OA?AI Na?oeaia A?eai??aia
Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y, aeioeaio
eaoaae?e oa?iaoeaaoe/ii? o?i??
Io?oe?ei? iiiiaioe: aeieoi? o?i?/ieo iaoe, i?ioani?
AIEIOIA Aaea??e Aaneeueiae/
Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y, caa?aeoth/ee
eaoaae?ith aiae?oe/ii? o?i??
aeieoi? oa?iaoeaaoe/ieo iaoe, i?ioani?
IAOTHI?I Aaiaae?e Iaaeiae/
Oa?e?anueeee ?inoeooo oaeineiiaeaiiy e?ea??a,
caa?aeoth/ee eaoaae?ith ee?i?/ii? a?io?i?? ? noaeiai-
iaaee/ii? oieneeieia??
I?ia?aeia onoaiiaa: Aea?aeaaiee iaoeiaee oeaio? e?ea?nueeeo cania?a
(i. Oa?e?a), eaai?aoi??y aeiiii?aeieo o?i?ei-
oa?iaoeaaoe/ieo ?a/iaei oa e?iainieiieo
iaoa??ae?a
Caoeno a?aeaoaeaoueny “ 16 ” ea?oiy 1999 ?ieo i __1200__ aiae.
ia can?aeaii? niaoe?ae?ciaaii? a/aii? ?aaee Ae 64.605.01 i?e
Oe?a?inuee?e oa?iaoeaaoe/i?e aeaaeai?? ca aae?anith: 310002, i. Oa?e?a,
aoe. Iooe?inueea, 53.
C aeena?oaoe??th iiaeia iciaeiieoeny a a?ae?ioaoe? Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai?? (310168, i. Oa?e?a, aoe. Aethoa?a, 4).
Aaoi?aoa?ao ?ic?neaiee “__13__”___aa?aciy_____ 1999 ?.
A/aiee nae?aoa? A?EOeAIEI ?.N.
niaoe?ae?ciaaii? a/aii? ?aaee
CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE
Aeooaeuei?noue oaie. ?icoe?aiiy a?naiaeo no/anieo e?ea?nueeeo cania?a
oeyoii noai?aiiy iiaeo aoaeoeaieo ? iaeioiene/ieo i?ea?iaeueieo
e?ea?nueeeo i?aia?ao?a — iaeia c iaeaaaeeea?oeo caaea/ oa?iaoeaaoe/ii?
iaoee oa i?aeoeee. Iaeiei c aoai?a ae??oaiiy oe??? i?iaeaie ?
oe?eani?yiiaaiee iiooe a?ieia?/ii aeoeaieo noanoaioe?e, aea/aiiy ?o
oa?iaeieia?/ieo oa o?ceei-o?i?/ieo oa?aeoa?enoee, anoaiiaeaiiy ca’yceo
i?ae no?oeoo?ith niieoe oa ?o oa?iaeieia?/iith ae??th.
Oe?iea canoinoaaiiy a iaaee/i?e i?aeoeoe? ciaeoee iio?aei? o?iie?io:
aioei?e?iai? caniae — ooi?o?iieiie (ii?oeienaoeei, iaoeienaoeei,
eiiaoeienaoeei oa ?io.), i?o?ienie?i; aiaeueaaoee — aeaoai?i;
a?iioie?oee — ooaeaiao?i; i?ioeiaey??ei? i?aia?aoe — o?iioeeae ?
ieaeaai?e oa aaaaoi ?ioeo.
Iia? iioaioe?ei? iiaeeeaino? a oeueiio ieai? iathoue 3-cai?uai?
4-a?ae?iene-2-ienio?iie?ie. Ia eaoaae?? oa?iaoeaaoe/ii? o?i??
Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai?? neioaciaaii iio?aeia
4-a?ae?iene-2-ienio?iie?io — aoaeoeaiee i?aia?ao i?noeaaiaianoacoth/i?
ae??, yeee c oni?oii i?ioiaeeoue ee?i?/i? aei?iaoaaiiy; iaea?aeaii
?a/iaeie c ae?aaeaiith aioeoe?ai?aeiith, i?ioei?e?iaiith,
i?ioecaiaeueiith aeoeai?noth. C ae?oaiai aieo ?ioa?an aei oeeo niieoe
iiynith?oueny oei, ui na?aae i?e?iaeieo a?ieia?/ii aeoeaieo ?a/iaei
o?iie?iiai? no?oeoo?e naia 3-cai?uai? a?ae?iene(ieni)o?iie?io (a oiio
/ene? — 3-aee?ecai?uai?) i?aaenoaaeai? iaea?eueo oe?iei, oa ?acii c oei,
i?aeoe/ii ia aea/aia ?o a?ieia?/ia aeoeai?noue.
Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie. Aeena?oaoe?y
aeeiiaia ca?aeii c ieaiii iaoeiai-aeine?aeieo ?ia?o Oe?a?inueei?
oa?iaoeaaoe/ii? aeaaeai?? c i?iaeaie IIC Oe?a?ie (iiia? aea?aeaaii?
?a?no?aoe?? 01.91.0002385).
Iaoa ? caaea/? aeine?aeaeaiiy. Iaoith ?iaioe ? neioac iiaeo a?ieia?/ii
aeoeaieo niieoe o ?yae? 3-cai?uaieo 4-a?ae?iene-2-ienio?iie?i?a oa ?o
iio?aeieo, a oaeiae aecia/aiiy iaea?eueo ia?niaeoeaieo c ieo aeey
iiaeaeueoiai ai?iaaaeaeaiiy ye iioaioe?eieo e?ea?nueeeo cania?a.
Aeey aeinyaiaiiy cacia/aii? iaoe aoee iinoaaeai? oae? caaea/?:
1. Cae?enieoe aeine?aeaeaiiy ?aaeoe?? oeeee?caoe?? aoeeiaiai ao??o
2-ea?aaoieneiaeiiai?eiai? eeneioe a oiiaao oa?iie?co.
2. ?ic?iaeoe i?aia?aoeai? niiniae iaea?aeaiiy oa cae?enieoe neioac
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a.
3. Iaea?aeaoe 4-I-aoeeeuei? iio?aei?
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a.
4. Aea/eoe ?aaeoe?th a?iioaaiiy 3-aee?e-,
3-ea?aaeeiene-4-a?ae?iene-2-ienio?iie?i?a oa
1-R-2,4-ae?ieni-3I-o?iie?i-3-ea?aiiiaeo eeneio.
5. Cae?enieoe neioac 5-R-1,3,4-o?aae?acie?e-2-ai?ae?a
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio.
6. Aea/eoe o?ceei-o?i?/i? aeanoeaino? neioaciaaieo niieoe.
7. I?iaanoe a?ieia?/iee ne?ei?ia neioaciaaieo niieoe oa aeyaeoe aeaiaioe
aca?iica’yceo “no?oeoo?a oa?iaeieia?/ia ae?y”.
8. A?ae?a?aoe iaea?eueo ia?niaeoeaio o?i?/io no?oeoo?o aeey iiaeeaeaieo
oa?iaeieia?/ieo aeine?aeaeaiue.
Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. I?e aea/aii? iiaaae?iee
aoeeiaiai ao??o 2-ea?aaoieneiaeiiai?eiai? eeneioe a oiiaao oa?iie?co
aia?oa iieacaia iiaeeea?noue cae?eniaiiy eiiaeainaoe?? Ae?eiaia aac
aeei?enoaiiy iniiaieo eaoae?caoi??a. Iiaeaeueoa aeine?aeaeaiiy
cacia/aiiai o?i?/iiai ia?aoai?aiiy aeicaieeei ?ic?iaeoe i?aia?aoeaio
iaoiaeeeo neioaco 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a, yea aeaea
iiaeeea?noue iaea?aeoaaoe oe?eueia? i?iaeoeoe c aenieeie aeoiaeaie i?e
i?i?iaeueieo cao?aoao.
Anoaiiaeaii iniaeeaino? a?iioaaiiy
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio, yea
noi?iaiaeaeo?oueny ?o aeaea?aieneethaaiiyi, ia iniia? /iai cai?iiiiiaaii
aoaeoeaiee neioac 1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?i?a.
Ca ?ic?iaeaieie iaoiaeeeaie neioaciaaia 71 iiaa niieoea, aoaeiaa oa
?iaeea?aeoaeuei?noue yeeo i?aeoaa?aeaeaia aeaiaioiei aiae?cii, iaoiaeaie
OO-, ?*-, II?-niaeo?ineii?? oa oiieioa?iai? o?iiaoia?ao??, a ie?aieo
aeiaaeeao – cono??/iei neioacii.
Aeine?aeaeaia aioeieneaeaioia, iaia?aiinoaa?e?coth/a, aioeoe?ai?aeia,
ae?o?aoe/ia, i?ioecaiaeueia, aioei?e?iaia, aioeeiaaoeyioia, aioe-A?E,
i?ioe?aeiaa, aa?a?oeeaeia oa ooia?oeeaeia aeoeai?noue neioaciaaieo
niieoe. Ca ?acoeueoaoaie aeine?aeaeaiiy a?ieia?/ii? aeoeaiino? aeyaeai?
ia?niaeoeai? niieoee c aioeieneaeaioiith, iaia?aiinoaa?e?coth/ith,
ae?o?aoe/iith oa ooia?oeeaeiith ae??th.
I?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a. ?ic?iaeai? iaoiaee neioaco
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a oa
1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?i?a iiaeooue aooe aeei?enoai? i?e
neioac? iiaeo a?ieia?/ii aeoeaieo niieoe. Cie?aia, cai?iiiiiaaiee niin?a
iaea?aeaiiy 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a oni?oii canoiniao?oueny
a neioac? ?ioeo 3-cai?uaieo 4-a?ae?iene-2-ienio?iie?i?a.
?acoeueoaoe a?ieia?/iiai ne?ei?iao, a oaeiae anoaiiaeai? ie?ai?
caeiiii??iino? i?ae no?oeoo?ith oa a?ieia?/iith ae??th
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a, ?o 4-I-aoeeeueieo iio?aeieo,
3-a?ii-3-aee?e-2,4-ae?ienio?iie?i?a, 5-R-1,3,4-o?aae?acie?e-2-ai?ae?a
1-R-4-a?ae?iene-2-ieni-o?iie?i-3-ea?aiiiaeo eeneio iiiiaieee aaco
aeaieo, yea ? iniiaith iiaeaeueoiai oe?eani?yiiaaiiai iiooeo
iioaioe?eieo e?ea?nueeeo i?aia?ao?a na?aae iio?aeieo o?iie?io.
A yeino? ia?niaeoeaiiai aaiaoii?ioaeoi?iiai caniao aeey iiaeaeueoeo
iiaeeaeaieo aeine?aeaeaiue cai?iiiiiaaii
3-iii?e-4-a?ae?iene-2-ienio?iie?i, aeey yeiai ?ic?iaeaii i?iaeo
oei/aniai? oa?iaeiiaeii? noaoo?.
?ic?iaeai? iaoiaee neioaco, a oaeiae ?acoeueoaoe o?ceei-o?i?/ieo oa
oa?iaeieia?/ieo aeine?aeaeaiue ai?iaaaeaeaii a iaoeiai-aeine?aeio ?iaioo
oa a iaa/aeueiee i?ioean eaoaae?e oa?iaoeaaoe/ii? o?i?? Caii??aenueeiai
iaaee/iiai oi?aa?neoaoo oa aenia?eiaioaeueii? eaai?aoi??? CAI “A?IE?E”.
Iniaenoee aianie caeiaoaa/a:
– iaaaaeaia a aeena?oaoe?? aenia?eiaoaeueia neioaoe/ia /anoeia ?iaioe,
?*- oa OO-niaeo?aeuei? aeine?aeaeaiiy, a oaeiae ?ic?iaea i?iaeoo OON
aeeiiai? iniaenoi aaoi?ii;
– aiae?c, ia?iaea oa ioi?ieaiiy ?acoeueoao?a neioaoe/ieo,
o?ceei-o?i?/ieo oa a?ieia?/ieo aeine?aeaeaiue i?iaaaeai? aeena?oaioii.
Ai?iaaoe?y ?acoeueoao?a aeena?oaoe??. Iniiaiee ci?no aeena?oaoe?eii?
?iaioe aeiiia?aeaany ia ?anioae?eainuee?e iaoeiai-i?aeoe/i?e
eiioa?aioe?? “No/ani? i?iaeaie oa?iaoe??” (Oa?e?a, 1994); i?aeia?iaei?e
iaoeiai-i?aeoe/i?e eiioa?aioe?? “Nia?aiaiiua aniaeou nicaeaiey,
enneaaeiaaiey e ai?iaaoeee eaea?noaaiiuo n?aaenoa” (Oa?e?a, 1995); ia
iaoeiai-i?aeoe/i?e eiioa?aioe??, i?enay/ai?e 75-??//th Oe?OA
“Aeinyaiaiiy no/anii? oa?iaoe?? – a iaaee/io i?aeoeeo” (Oa?e?a, 1996).
Ioae?eaoe??. Iaoa??aee aeena?oaoe?? iioae?eiaai? o 5 noaooyo, 3 oacao
aeiiia?aeae oa 2 aeaiiiiaaieo ?oeiienao.
No?oeoo?a aeena?oaoe??. Aeena?oaoe?eia ?iaioa neeaaea?oueny c anooio,
o?ueio ?icae?e?a, aeniiae?a, nieneo e?oa?aoo?ieo aeaea?ae, aeiaeaoe?a.
Caaaeueiee ia’?i aeena?oaoe?? neeaaea? 132 noi??iee. ?iaioa ?ethno?iaaia
7 noaiaie, 3 iaethieaie ? 20 oaaeeoeyie. Ia?ae?e aeei?enoaieo
e?oa?aoo?ieo aeaea?ae i?noeoue 136 iaeiaioaaiue.
INIIAIEE CI?NO ?IAIOE
1. Neioac, o?i?/i? ia?aoai?aiiy oa a?ieia?/i? aeanoeaino? 3-
aee?ecai?uaieo 4-a?ae?iene-2-ienio?iie?i?a
Na?aae /eneaiieo i?e?iaeieo niieoe o?iie?iiai? no?oeoo?e iniaeeaee
?ioa?an aeeeeeathoue 3-aee?ecai?uai? 4-a?ae?iene-2-ienio?iie?ie, ye?
iathoue oe?ii? a?ieia?/i? aeanoeaino?, aea aea/ai? cian?i iaei.
Iaea?eueo iioe?ai? a?aeii? iaoiaee neioaco
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a iniiaai? ia aoeeethaaii? ai?e?i?a
aee?eiaeiiiaeie ao??aie c iaeii/aniith oa?i?/iith oeeee?caoe??th
ai?e?ae?a, ye? i?e oeueiio ooai?ththoueny, aai ia aoeeethaaii?
aee?eaio?ai?eao?a oei?aia?ae?eaeaie iiiiaoeeiaeo ao???a aee?eiaeiiiaeo
eeneio c ianooiiei caieeaiiyi o?iieiiiaiai oeeeeo ca Aeeeiaiii.
Iniiai? iaaeie?ee oeeo iaoiae?a iia’ycai? c ooai?aiiyi neiao?e/ieo
ae?ai?e?ae?a a ia?oiio aeiaaeeo oa iaeith aeinooii?noth aoeeethth/eo
aaaio?a a ae?oaiio. E??i oiai, a aeayeeo aeiaaeeao ia?oee iaoiae acaaae?
ia i?eaiaeeoue aei aaaeaieo ?acoeueoao?a. Aeoiaey/e c oeueiai, iaie aoee
c?iaeai? ni?iae oaeineiiaeaiiy iaoiae?a neioaco
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a.
Oaea iiaeeea?noue c’yaeeanue a ?acoeueoao? aeine?aeaeaiiy ?aaeoe??
oa?iie?co ao???a 2-ea?aaeeieneiaeiiai?eiaeo eeneio (Noaia 1). Oae, i?ney
eei’yo?iiy aoeeiaiai ao??o 2-ea?aaoieneiaeiiai?eiai? eeneioe (1) a
aeeoai?eieneae? iaie aeae?eaii 2-ea?aaoieneai?e?ae
4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiai? eeneioe (2). sse a?aeiii, i??ie?c
aoeeiaeo ao???a iaeiiai?eiaeo eeneio aai ?o eei’yo?iiy a AeIOA
i?eaiaeeoue aei neiao?e/ieo ae?ai?e?ae?a. I/aaeaeii, a aeaiiio aeiaaeeo
ia?oith noaae??th ? ooai?aiiy ae?ai?e?aeo 3. Iaa?yae /e iiaeia iiynieoe
oeeee?caoe?th oe??? niieoee a o?iieii 2 a oiiaao oa?iie?co caeaoi?noth
iio?aeieo iaeiiiai? eeneioe ooai?thaaoe noaa?euei? ea?aai?iie,
ine?eueee, ii-ia?oa, aeo?aeiee ae?ao?? 1 oeeee?coaaany a a
4-a?ae?iene-3-ea?aaoiene-2-ienio?iie?i, a, ii-ae?oaa, eei’yo?iiy
ae?aoeeiaeiiaoo 4 c iaaeeeoeii aoeeaio?ai?eaoo 5 i?eaiaeeoue aei
ooai?aiiy eeoa ae?ai?e?aeo 3. ?ioeie neiaaie, iniiaieo aeanoeainoae
ai?iia?oie aoeeaio?ai?eaoo, eiia??i?noue ooai?aiiy yeiai iiaeia
i?eionoeoe a ?acoeueoao? oa?iie?co ae?ao??o 1, yaii iaaeinoaoiuei aeey
cae?eniaiiy oeeee?caoe?? ca oeiii ?aaeoe?? Ae?eiaia.
Noaia 1
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:???0????? ???? ???u??????????”????-????? ????
???u?????????”????-??????????E?4???4???Y?T???hT
??? ???? ???u??????????”????-?????????? ????
???u?????????”????-??????????4???*I??? ????
???u??????????”????-?????????? ????
???u?????????”????-??????????*I???l???°N???kJ
??? ???? ???u??????????”????-?????????? ????
???u?????????”????-??????????l???E?l??? ????
???u??????????”????-?????????? ????
???u?????????”????-??????????E?l???n?I???U?J???”?N
???n?I???E?4???E?l?????Oe??? ????
???u??????????”????-??????????u?y?????? Ana iaaaaeaia aeicaiey?
i?eionoeoe, ui aeaia ?aaeoe?y aeeth/a? noaae?th aioo??oiueiiieaeoey?ii?
aca?iiae?? a ?iieuei?e oi?i? 6, a ye?e ea?aii?euei?e aoii aoaeaoeth
neeaaeiiao??iiai oa?oioaaiiy aenooia? a ?ie? aeaeo?io?eo, a ?iie – ye
ioeeaio?e. Caieeaiiy o?iieiiiaiai oeeeeo 7, yea i?e oeueiio
a?aeaoaa?oueny, i?eaiaeeoue aei 2,4-ae?ieniiio?aeiiai 8 ? a e?ioeaaiio
?acoeueoao? – aei o?iieiio 2.
I?ii?aeia ooai?aiiy 2,4-ae?ienio?iie?io 8 iiaeia i?aeoaa?aeeoe ia
i?eeeaae? oa?iie?co N,N’-aee-2-ea?aaoieneai?e?aeo iaoeeiaeiiiai? eeneioe
12 (Noaia 2).
Noaia 2
wmetafile8? ?????? ????????yyy????c–???NO???? ????
???u??????????”????-????? ????
???u?????????”????-?????????????????*????*?
?? ???? ???u??????????”????-?????????? ????
???u?????????”????-??????????????Y??? ????
???u??????????”????-?????????? ????
???u?????????”????-??????????Y????B???o§???
??? ???? ???u??????????”????-?????????? ????
???u?????????”????-???????????B???B??? ????
???u??????????”????-?????????? ????
???u?????????”????-??????????B???°Y???
???Oe§???°Y??????B???I§??? ????
???u??????????”????-??????????u?y??????
A eeane/ieo oiiaao eiiaeainaoe?? Ae?eiaia iaei??th c i?ii?aeieo niieoe
oaeiae ? 2,4-ae?ieniiio?aeia 8, iaeiae a oeueiio aeiaaeeo aeey oiai, uia
?aaeoe?y iiaea eoe a iio??aiiio iai?yieo, iaiao?aeia iiaeeea?noue
ooai?aiiy ai?iio niieoee 10. Oaea ia?aoai?aiiy noi?iaiaeaeo?oueny
ae?i?ioaaiiyi i?ioiia (a ia eiai ia?aiinii, ye o aeiaaeeo oa?iie?co) ?
i?eaiaeeoue aei ai?iio 11, i?ney i?aeeeneaiiy yeiai aaea iiaea aooe
aeae?eaiee o?iieii 2.
Oaeei /eiii, iao? aeine?aeaeaiiy iieacaee iiaeeea?noue cae?eniaiiy
eiiaeainaoe?? Ae?eiaia ? i?e a?aenooiino? iniia, ui aeicaieeei
?icaeyiooe aeaio ?aaeoe?th c aeae?eueea ?ioi? oi/ee ci?o, yea
a?ae??ci??oueny a?ae ?? eeane/iiai iaaaaeaiiy.
Ne?ae cacia/eoe, ui ?icaeyiooa aeua ?aaeoe?y ooai?aiiy 3,3-aeecai?uaieo
2,4-ae?ienio?iie?i?a a ?acoeueoao? oa?iie?co neiao?e/ieo
aee-2-ea?aaeeieneai?e?ae?a aee?eiaeiiiaeo eeneio (Noaia 2) i?aaenoaaey?
oaeaeoa oai?aoe/iee ?ioa?an, i?ae i?aeoe/iee, ine?eueee ?? i?aeoe/ia
aeei?enoaiiy, ia aeaeue, aeineoue iaiaaeaia. A oie aea /an, iiaeaeueoa
?? aea/aiiy i?eaaei aei oe?eaai? neioaoe/ii? ciao?aeee.
sse aeyaeeinue, a i?enooiino? iniia, oiaoi a oiiaao eiiaeainaoe??
Ae?eiaia, N,N’-aee-2-ea?aaeeieneai?e?aee aee?eiaeiiiaeo eeneio (15) c
aenieeie aeoiaeaie ooai?ththoue a?aeiia?aei?
3-aee?e-4-a?ae?iene-2-ienio?iie?ie (14). Iaoai?ci ia?oeo aeaio noaae?e
caieeaiiy o?iieiiiaiai e?eueoey o aeaiiio aeiaaeeo aiaeia?/iee
oeeee?caoe?? ae?ai?e?aeo 3 (Noaia 1). Iiaeaeueoee aea ia?aa?a ?aaeoe??
ia? nai? iniaeeaino?, ine?eueee iaiao?aeia ia caaa?oaeuei?e noaae??
ooai?aiiy ai?iio e?ioeaaiai o?iieiio 15a iiaeeeaa eeoa o aeiaaeeo
a?aeuaieaiiy iaeiiai c cai?niee?a i?e aoii? aoaeaoeth a iieiaeaii? 3
niieoee 15a. Oaeei cai?nieeii aeyaeeinue ea?aai?e?aeia oa?oioaaiiy, yea,
i/aaeaeii o aeaeyae? o?aoaio, ? a?eueo eaaei iieeaeath/ei o?aaiaioii,
i?ae aee?eueiee cai?niee (Noaia 3).
Noaia 3
wmetafile8? ???!???????????yyy????th h?????ey??? ????
???u??????????”????-??
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-?????.????u?y??????1/4???I???Times New Roman
Cyr?I???-????????2e:???15???-?????????'yy???-?
???-????? ????
???u?????????"????-??????????????%;??? ????
???u??????????"????-?????????? ????
???u?????????"????-??????????p???%???…7???7
??? ???? ???u??????????"????-?????????? ????
???u?????????"????-??????????%??????? ????
???u??????????"????-?????????? ????
???u?????????"????-??????????????%O???X?
???-??? ???? ???u??????????"????-?????????? ????
???u?????????"????-??????????%O???pO??? ????
???u??????????"????-?????????? ????
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Ine?eueee neioac ae?ai?e?ae?a 15 iaaecae/aeii i?inoee, oi a oe?eiio
aeaiee iaoiae iiaeia ?aeiiaiaeoaaoe ye i?aia?aoeaiee. Iaeei c eiai
iaaeie?e?a — ia?aoe?iiaeueia aeei?enoaiiy aee?eaio?ai?eao?a. Iaeiae ?
oeae iaaeie?e o a?eueoino? aeiaaee?a aaea?oueny onoiooe oeyoii i?aeai?o
iaea?eueo iioeiaeueiiai ni?aa?aeiioaiiy ?aaaaio?a.
sse a?aeiii, aoeeethaaiiy ai?e?i?a ae?aoeeiaeiiaoaie i?aeoe/ii caaaeaee
noi?iaiaeaeo?oueny ooai?aiiyi neiao?e/ieo ae?ai?e?ae?a. E??i oiai,
aenia?eiaioaeueii anoaiiaeaii, ui iaa?oue aeae?eai? a /enoiio aeaeyae?
aoeeia? ao??e iaeiiai?eiaeo eeneio a aiaeia?/ieo oiiaao (iaa??aaiiy aei
170...200iN) eaaei ia?aoai?ththoueny a ae?ai?e?aee c ae?i?ioaaiiyi
a?aeiia?aeieo ae?aoeeiaeiiao?a. A?aoiaoth/e oea, i?e aoeeethaaii?
iaoeeaio?ai?eaoo 16 ae?aoeeiaeiiaoaie 17 c ieae/eie aee?eueieie
cai?nieeaie aeioe?eueii aaiaeeoe a ?aaeoe?th iiaea?eiee iaaeeeoie
aio?ai?eaoo. C iiaeiaaeaiiyi aoaeaaiaeiaaiai eaioethaeea aee?eueiiai
cai?nieea aoeeethth/a caeaoi?noue ae?oai? aoieneea?aii?eueii? a?oie
iaeiiiaeo ao???a 17 iaaea? iano?eueee (i/aaeaeii, aiane?aeie noa?e/ieo
ia?aoeiae), ui caaeia?euei? ?acoeueoaoe iiaeia iaea?aeaoe aaea ? i?e
aea?iiey?ieo ni?aa?aeiioaiiyo ao???a 16 oa 17.
sse ua iaeei iiceoeaiee iiiaio ne?ae a?aei?oeoe oa, ui aeaiee niin?a ia
iio?aao? ?icae?eaiiy iiii- ? ae?ai?e?ae?a aee?eiaeiiiaeo eeneio 18 oa
15, ye? a ??cieo ni?aa?aeiioaiiyo caaaeaee i?enooi? a ?aaeoe?ei?e noi?o?
(Noaia 4).
Noaia 4
wmetafile8? ????? ?????????yyy????a???Oa??? ????
???u??????????"????-?????u?y??????
14 R = H: a R = CH3; a R = C2H5; a R = CH2CH=CH2; a R = C3H7; ae
R = i-C3H7;
a R = C4H9; ae R = C5H11; c R = C6H13; e R =
C7H15; e R = C8H17; e C9H19;
i R = C10H21; i R = C12H25; i R = CH2C6H5; R =
CH3; i R = C4H9
Cia/ii ?icoe?th? iiaeeeaino? iaoiaeo aeei?enoaiiy ye aoeeethth/eo
aaaio?a aeinooiieo aeeoei?aia?ae?eae?a aee?eiaeiiiaeo eeneio 20, yea
aeicaiey? eaaei neioacoaaoe ye 1I-3-aee?e-4-a?ae?iene-2-ienio?iie?ie
14a-i, oae ? ?o 1-cai?uai? aiaeiae 14i.
O?i?/ia aoaeiaa 3-aee?ecai?uaieo 4-a?ae?iene-2-ienio?iie?i?a 14
i?aeoaa?aeaeaia aeaiaioiei aiae?cii oa aeaieie II?- ? OO-niaeo?ineii??.
Iaeiei c iaoiae?a noai?aiiy iiaeo e?ea?nueeeo cania?a, ye a?aeiii, ?
neioac i?ie?e?a, oiaoi o?i?/ia iiaeeo?eaoe?y a?aeiiiai i?aia?aoo c o??th
/e ?ioith iaoith: iineeaiiy aeoeaiino?, iiaeiaaeaiiy o?eaaeino? ae??,
cieaeaiiy oiene/iino?, onoiaiiy iai?e?iiiai niaeo oa ?io.
Aeei?enoiaoth/e oeae i?eioeei, c iaoith aeyaeaiiy caeiiii??iinoae
ca’yceo “o?i?/ia aoaeiaa — a?ieia?/ia aeoeai?noue” iaie iaea?aeai?
4-I-aoeeeuei? iio?aei? 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a 22. Neioac
cae?eniaii aoeeethaaiiyi 4-a?ae?ieneiio?aeieo 14 aia?ae?eaeaie /e
oei?aia?ae?eaeaie ea?aiiiaeo eeneio:
Noaia 5
wmetafile8? ??&???
????????yyy????yr????.??? ????
???u??????????"????-?????u?y??????
22 a Alk = i-Pr, R = Me; a Alk = Pr, R = Et; a Alk = Pr, R =
CH2CH2COOMe;
a Alk = Bu, R = Me; ae Alk = Bu, R = CH2Cl; a Alk = i-Bu, R
= Me; ae Alk = NH2-Ph,
R = Me; c Alk = NH2-Ph, R = Ph; e Alk = NH2-Ph, R = C15H31
I?iaeiaaeoth/e aeine?aeaeaiiy ii iiooeo iioaioe?eieo aioei?e?iaieo
e?ea?nueeeo cania?a na?aae aaei?aecai?uaieo o?iie?i?a, iaie aea/aia
iiaaae?iea 3-cai?uaieo 4-a?ae?iene-2-ienio?iie?i?a a oiiaao a?iioaaiiy
iieaeoey?iei a?iiii (Noaia 6). I?e oeueiio anoaiiaeaii, ui a eueiaeyi?e
ioeoia?e eeneio? 3-aee?ecai?uai? 4-a?ae?iene-2-ienio?iie?ie (14) eaaei
ooai?ththoue 3-a?ii-3-aee?e-2,4-ae?ienio?iie?ie 23 c aenieeie aeoiaeaie.
sse ? ne?ae aoei /aeaoe, ia?iaea inoaii?o iaoeeaoii iao??th aea?
3-iaoieneiio?aei? 24, oiae? ye o?ao-aooeeao eae?th aeeeeea? oaeaeea
aeaa?ae?ia?iioaaiiy c ooai?aiiyi aeo?aeieo 3-aee?eo?iie?i?a 14.
Ne?ae cacia/eoe oe?eaao iiaaae?ieo a oiiaao aeine?aeaeoaaii? ?aaeoe??
1-R-2,4-ae?ieni-3I-o?iie?i-3-ea?aiiiaeo eeneio (25). sseui aoeeia? ao??e
26, iiae?aii aei 3-aee?eo?iie?i?a 14, ooai?ththoue a?aeiia?aei?
3-a?ii-2,4-ae?ieniiio?aei? 27, oi i?ney ia?iaee a?iiii eeneio 25 c
?aaeoe?eii? noi?o? aeae?eai? 1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?ie 28,
aoaeiaa yeeo i?aeoaa?aeaeaia cono??/iei neioacii, a naia eeneioiei
a?ae?ie?cii ao???a 27. Neeueii ae?aaeai? eeneioi? aeanoeaino?, a ioaea ?
eaae?noue aeaea?aieneethaaiiy 3-a?ii-2,4-ae?ienio?iie?i-3-ea?aiiiaeo
eeneio 29, ye? nii/aoeo ooai?ththoueny, iiaeia iiynieoe
aeae?eueeiia oaeoi?aie. Ii-ia?oa, iiaeeea?noth noaa?e?caoe?? ai?ii?a
eeneio 25 ca ?aooiie aeaeieae?caoe?? ?o ca?yae?a oeyoii ooai?aiiy
aioo??oiueiiieaeoey?ieo aiaeiaaeo ca’yce?a ca oeiii i?oi-aoaeoa o
i-a?ae?iene- ?, iniaeeai, i-aeea?ae?ieneaaicieieo eeneio. I/aaeaeii,
naia oeei oaeoi?ii iiynith?oueny eaea?noue ai?aeoaaiiy
1-R-2,4-ae?ieni-3I-o?iie?i-3-ea?aiiiaeo eeneio. Ii-ae?oaa, aaaaeaiiy
aeaeo?iiiaeoeaioi?iiai cai?nieea (aoiia a?iio) a -iieiaeaiiy ii
a?aeiioaiith aei ea?aieneeueii? a?oie coiiaeth? ua a?eueo nooo?aa
i?aeaeuaiiy eeneioiino?. Eiia??ii, ii?aeiaiiy cacia/aieo aoaeo?a ?
i?ecaiaeeoue aei oiai, ui a?iicai?uai? eeneioe 29 aeaea?aieneeththoueny
aaea i?e e?iiaoi?e oaiia?aoo??. A?aoiaoth/e i?inoioo neioaco
1-R-2,4-ae?ieni-3I-o?iie?i-3-ea?aiiiaeo eeneio 25 oa aeaaeea i?io?eaiiy
?o a?iioaaiiy, aeaiee iaoiae iiaeia ?aeiiaiaeoaaoe ye i?aia?aoeaiee aeey
iaea?aeaiiy 1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?i?a (28).
An? iaaaaeai? ia noai? 6 a?iicai?uai? o?iieiie yaeythoue niaith
na?oei-aeiao? e?enoae?/i? ?a/iaeie c /?oeeie oaiia?aoo?aie ieaaeaiiy,
i?aeoe/ii ia?ic/eii? o aiae? oa aeia?a ?ic/eii? a a?eueoino? i?aai?/ieo
?ic/eiiee?a. ?o o?i?/ia aoaeiaa i?aeoaa?aeaeaia ye aeaiaioiei aiae?cii,
oae ? niaeo?aeueieie iaoiaeaie.
Iacaaaeath/e ia oe?iea ?iciianthaeaeaiiy o i?e?iae?,
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a eeoa a iaaaaaoueio ioae?eaoe?yo
iaaiaeyoueny a?aeiiino? i?i aea/aiiy ?o a?ieia?/ieo aeanoeainoae,
i?e/iio /ano?oa o?eueee i?i aioei?e?iaio oa ooia?oeeaeio aeoeai?noue.
Aeoiaey/e c oeueiai, neioaciaai? iaie
3-aee?e-4-a?ae?iene-2-ienio?iie?ie 14 aoee i?aeaeai? oa?iaeieia?/iiio
ne?ei?iao ia aeyaeaiiy aioeoe?ai?aeii?, i?ioecaiaeueii?, aioei?e?iaii?,
iaia?aiinoaa?e?coth/i? ? aioeieneaeaioii? aeoeaiino?. Aea/aii oaeiae
aieea oeeo ?a/iaei ia aeae?eueio ooieoe?th ie?ie oa nenoaio cn?aeaiiy
e?ia?. A?aoiaoth/e iniaeeao aeooaeuei?noue iiooeo oa noai?aiiy
e?ea?nueeeo i?aia?ao?a, i?eaeaoieo aeey e?eoaaiiy NI?Aeo ? iieieia?/ieo
caoai?thaaiue, aeaye? c neioaciaaieo iaie ?a/iaei i?ieoee ia?aa??eo ye
iioaioe?ei? aioe-A?E ? i?ioe?aeia? aaaioe.
Noaia 6
wmetafile8? ??“%???????????yyy????3/4d???·“???? ????
???u??????????"????-?????u?y??????
14, 23 a R = CH3, a R = C2H5, a R = C3H7, a R = C4H9, ae R =
C5H11, a R = C6H13,
ae R = C7H15, c R = C8H17, e R = CH2C6H5;
26, 27 a R = H, a R = CH3, a R = C2H5;
25, 28 a R = CH3, a R = C2H5, a R = C6H13
sse aeyaeeinue, niieoee 14a-i i?iyaeththoue aenieo aioeieneaeaioio
aeoeai?noue ? a a?eueoino? aeiaaee?a aeinoia??ii ia?aaeuothoue i?aia?ao
ii??aiyiiy (a?oai?i A).
Ae?aaeaia iaia?aiinoaa?e?coth/a ae?y niinoa??aaeanue aeey niieoe
14a,ae,e, ye? ia?aaeuothoue aeoeai?noue nee?ai?o, a niieoee 14ae,a,i
ae?thoue ia ??ai? inoaiiueiai. Ne?ae cacia/eoe, ui niieoee 14e,ae,?,a
aeyaeythoue i?e oeueiio ua e aenieo aioeieneaeaioio ae?th.
Oe?eaaa oaiaeaioe?y i?iaeyaea?oueny i?e aea/aii? o?iieii?a 14 ia
na/iaeae?eueio ooieoe?th ie?ie. Aeyaeeinue, ui ?a/iaeie, ye? i?noyoue
ia?io e?euee?noue aoii?a aoaeaoeth a aee?eueiiio cai?nieeo (14a,c,i),
i?iyaeythoue ae?aaeaio na/ia?iio ae?th, eeoa aeaui iinooiath/enue
a?iio?aceaeo. A oie aea /an, o?iieiie c iaia?iei /eneii aoiiia aoaeaoeth
a aee?eueieo eaioethaeeao ca ??aeeei aeeeth/aiiyi aai acaaae? ia
aieeaathoue ia na/iaeae?eaiiy, aai ae aeeeeeathoue neeueia cieaeaiiy
ae?o?aco, ia?aaaaeath/e ca aeoeai?noth (iai?eeeaae, o?iieii 14ae)
aioeae?o?aoe/iee ai?iii aae?o?ae?ei.
Ae?aaeaia aioeeiaaoeyioa ae?y o ii??aiyii? n oai?iia?iiii
niinoa??aaeanue o 3-aaicee-4-a?ae?iene-2-ienio?iie?io (14i).
Uiaei ?ioeo a?ieia?/ieo aei?iaoaaiue 3-aee?e-4-a?ae?iene-2-ienio?iie?ie
14, oi aiie iieacaee, ui oe? niieoee aeyaeythoue neaaeiae?aaeaio
aioeoe?ai?aeio aeoeai?noue; i?aeoe/ii iaaeoeaieie aiie aeyaeeenue i?e
aeine?aeaeaii? i?ioecaiaeueii?, aioei?e?iaii?, aioe-A?E oa aioe?aeiai?
ae??.
Aeey 4-I-aoeeeueieo cai?uaieo 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a (22)
aoea aeine?aeaeaia aioeieneaeaioia, iaia?aiinoaa?e?coth/a, ae?o?aoe/ia ?
i?ioecaiaeueia aeoeai?noue. sse ? o aeiaaeeo niieoe 14, iaea?eueo
aoaeoeaieie ?o 4-I-aoeeeuei? aiaeiae aeyaeeeny a ieai? i?iyaeaiiy
aiioeieneaeaioii? oa iaia?aiinoaa?e?coth/i? ae??. I?e oeueiio, iaea?eueo
aeniea iaia?aiinoaa?e?coth/a aeoeai?noue, yea ia?aaeuoa ??aaiue
nee?ai?o, yiinoa??aaeany o ?a/iaei, ye? i?noyoue caeeoie ioeoiai?
(22a,a) aai oei?ioeoiai? (22ae) eeneio. Ca?eueoaiiy e?eueeino? aoii?a
aoaeaoeth a aoeeeueiiio o?aaiaio? i?ecaiaeeoue aei cieaeaiiy
iaia?aiinoaa?e?coth/i? aeoeaiino?, a aaaaeaiiy caeeoeo aeeea?aiiiai?
eeneioe (22a) - ia o?eueee aei iiaii? ?? ao?aoe, a e aei i?aeaeuaiiy
eiioeaio?aoe??? AeAO.
A?aei?/aia iaie ?ai?oa aeey 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a (14)
caeaaei?noue na/iaea?aeii? ae?? a?ae e?eueeino? aoii?a aoaeaoeth a
aee?eueiiio caeeoeo, ia i?inoaaeo?oueny o ?o 4-I-aoeeeueieo iio?aeieo
22, ye? aeyaeythoue ae?aaeaio ae?o?aoe/io ae?th, yea, iaeiae, ia
ia?aaeuo? i?aia?ao ii??aiyiiy - a?iioeaceae.
Aeine?aeaeaiiy i?ioecaiaeueii? aeoeaiino? niieoe 22, iieacaei, ui, ia
aeaeue, aeey 4-I-aoeeeueieo iio?aeieo
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a i?ioecaiaeueia aeoeai?noue ia
oa?aeoa?ia.
Aeey 3-a?ii-3-aee?e-2,4-ae?ienio?iie?i?a (23) aoei aeine?aeaeaii
aioei?e?iaio aeoeai?noue, yeo iiaeia ioa?aeoa?ecoaaoe ye neaaiae?aaeaio.
Oaeei /eiii, i?iaaaeai? oa?iaeieia?/i? aeine?aeaeaiiy a?aee?eaathoue
ia?niaeoeao noai?aiiy iiaeo e?ea?nueeeo i?aia?ao?a ia iniia? iio?aeieo
4-a?ae?iene-2-ienio?iie?i?a. Cie?aia, 3-iii?e-4-a?ae?iene-2-ienio?iie?i
(14e), yeee aeyaey? aenieo iaia?aiinoaa?e?coth/o oa aioeieneaeaioio
aeoeai?noue, ?aeiiaiaeiaaiee aeey iiaeeaeaieo oa?iaeieia?/ieo
aeine?aeaeaiue ye iioaioe?eiee aaiaoii?ioaeoi?iee can?a, a ca’yceo c /ei
iaie ?ic?iaeaii i?iaeo oei/aniai? oa?iaeiiaeii? noaoo? ia oeth ?a/iaeio.
2. Neioac, o?ceei-o?i?/i? oa a?ieia?/i? aeanoeaino? 5-R-1,3,4-o?aae?a-
cie?e-2-ai?ae?a 1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio
Noai?aiiy oa ai?iaaaeaeaiiy a iaaee/io i?aeoeeo iiaeo aoaeoeaieo
aioeaaeoa??aeueieo cania?a caaea/a, yea iino?eii iio?aao? ae??oaiiy,
caaaeath/e ia iiyao i?ae aieeaii /ano iiaeo no?eeeo ooai?a iaoiaaiii?
i?e?ioei?e.
A ?acoeueoao? aeine?aeaeaiue, i?iaaaeaieo ?ai?oa ia eaoaae??
oa?iaoeaaoe/ii? o?i?? Oe?a?inueei? oa?iaoeaaoe/ii? aeaaeai??, aeineoue
aeniea aioei?e?iaia aeoeai?noue aoea aeyaeaia o iio?aeieo
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio oa 1,3,4-o?aae?acieo.
Ia’?aeiaiiy a iaei?e iieaeoe? oaeeo aeoeiaeo o a?ieia?/iiio a?aeiioaii?
no?oeoo? ye N-aee?e-4-a?ae?ieneo?iie?i-3-ea?aiiia? eeneioe ?
5-R-1,3,4-o?aae?aciee noai?th? ?aaeuei? ia?aaeoiiae aeey neioaco
aoaeoeaieo oa?iaeieia?/ieo cania?a, ui ? iineoaeeei oai?aoe/iei
iaa?oiooaaiiyi aeine?aeaeaiue o oeueiio iai?yieo.
Ai?aee 31a-y aoee iaea?aeai? oa?iie?cii aea?iiey?ieo e?eueeinoae
aoeeiaeo ao???a 1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio 26 ?
2-ai?ii-5-R-1,3,4-o?aae?acie?a 30 o a?aeiia?aeiino? aei iaoiaeeee,
?ic?iaeaii? iaie ?ai?oa, ca noaiith 7.
Neioaciaai? niieoee yaeythoue niaith aacaa?ai? e?enoae?/i? ?a/iaeie c
/?oeeie oaiia?aoo?aie ieaaeaiiy, i?aeoe/ii ia?ic/eii? o aiae? oa
a?eueoino? i?aai?/ieo ?ic/eiiee?a.
Aioei?e?iaio aeoeai?noue iaea?aeaieo niieoe aecia/aee ii a?aeiioaiith
aei oaeeo oano-ooai?a: Staphylococcus aureus (ATCC 25923), Escherichia
coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 25853) ? Bacillus
subtilis (ATCC 66330).
Aeine?aeaeaiiy iieacaee, ui c 20 ia?aa??aieo niieoe aioei?e?iaio
aeoeai?noue ii a?aeiioaiith aei ??cieo ooai?a i?e?ii?aai?ci?a o
eiioeaio?aoe?? 31,25-
Noaia 7
wmetafile8? ??
???????????yyy????ma???aeO???? ????
???u?????????"????-?????X31 R= H: a R = H; a R = Me; a R =
Et; a R = Pr; ae R = i-Pr; a R = Bu; ? R = i-Bu;
ae R = SO2NH2
R = Me c R = H; e R = Me; ? R = Et; e R = Pr; e R = i-Pr; i R = Bu; i
R = SO2NH2
R = Et i R = H; i R = Me; ? R = Et; n R = Pr; o R = i-Pr; o R = Bu; o
R = SO2NH2
R = Pr o R = H; oe R = Me; / R = Et; o R = Pr; u R = i-Pr; th R = Bu;
y R = SO2NH2
62,5 iea/ie i?iyaeee 7 ?a/iaei, i?e/iio niieoea 31o aeyaeeany aeoeaiith
ii a?aeiioaiith aei an?o aeei?enoaiieo oano-ooai?a. Ne?ae cacia/eoe, ui
ca oeiii aioei?e?iaii? ae?? an? aeine?aeaeoaai? niieoee ?
aaeoa??inoaoeeaie.
Aiae?coth/e ?acoeueoaoe aeine?aeaeaiue, iiaeia c?iaeoe aeniiaie, ui
aecia/aeueieie oaeoi?aie i?iyaeaiiy aea??eiai? aioei?e?iaii? aeoeaiino?
? iayai?noue ?icaaeoaeaiiai aee?eueiiai cai?nieea a iieiaeaii? 5
o?aae?acieueiiai oeeeeo. A oie aea /an i?enooi?noue N1-N4 aee?eueieo
cai?niee?a a iieiaeaii? 1 o?iie?iiaiai oeeeeo ?noioiiai aieeao ia
aioei?e?iaio ae?th ia ia?.
Aea/aiiy aa?a?oeeaeii? aeoeaiino? niieoe 31 ia aeyaeei aeoeaieo a
oeueiio ieai? ?a/iaei. A?eueo aoaeoeaii o?aae?acie?e-2-ai?aee
1-R-4-a?ae?iene-2-ieni-o?iie?i-3-ea?aiiiaeo eeneio (31) iiaeooue aooe
canoiniaai? ye ooia?oeeaee. Iniaeeai aeoeaieie aeaye? c aeine?aeaeaieo
?a/iaei, a naia 31a,?,u, aeyaeeenue o ai?iouea? c eenoeiaith ??aeath,
ie?eeoey??icii ?eno oa ieyieno?noth eieineiai? eonee ioaieoe?, ui
a?aee?eaa? ia?niaeoeao noai?aiiy ia iniia? o?aae?acie?e-2-ai?ae?a
1-R-4-a?ae?iene-2-ieni-o?iie?i-3-ea?aiiiaeo eeneio (31) iioaioe?eieo
ooia?oeeae?a aeey n?euenueeiai ainiiaea?noaa.
AENIIAEE
1. Aia?oa iieacaia iiaeeea?noue cae?eniaiiy eiiaeainaoe?? Ae?eiaia a
oiiaao, a?aei?iieo a?ae eeane/ieo — i?e a?aenooiino? iniiaieo
eaoae?caoi??a; cai?iiiiiaaii eiia??iee iaoai?ci oeueiai o?i?/iiai
ia?aoai?aiiy.
2. Cae?eniaii neioac a?ieia?/ii aeoeaieo ?a/iaei a ?yae? 3-cai?uaieo
a?ae?iene(ieni)o?iie?i?a: 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a;
4-I-aoeee-3-aee?e-4-a?ae?iene-2-ienio?iie?i?a;
3-a?ii-3-aeeee-2,4-ae?ienio?iie?i?a; 5-R-1,3,4-o?aae?acie?e-2-ai?ae?a
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio.
3. ?ic?iaeaii i?aia?aoeaiee niin?a iaea?aeaiiy
3-aee?e-4-a?ae?iene-2-ienio?iie?i?a. I?e oeueiio ?aoe?iiaeueia
aeei?enoaiiy aeo?aeieo aee?eaio?ai?eao?a aeinyaa?oueny oeyoii i?aeai?o
iioeiaeueiiai ni?aa?aeiioaiiy ?aaaaio?a a caeaaeiino? a?ae no?oeoo?e
aee?eueiiai cai?nieea. Cai?iiiiiaaiee iaoiae ciaeoia canoinoaaiiy a
i?aai?/i?e o?i?? oeyoii iioe?aiiy ia neioac ?ioeo 3-cai?uaieo
4-a?ae?iene-2-ienio?iie?i?a.
4. Cae?eniaii ia?aoai?aiiy 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a a oiiaao
?aaeoe?e aoeeethaaiiy oa a?iioaaiiy.
5. Cai?iiiiiaaii i?inoee oa aoaeoeaiee neioac
1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?i?a, yeee cae?enith?oueny a?iioaaiiyi
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio, yea
noi?iaiaeaeo?oueny aeaea?aieneethaaiiyi inoaii?o.
6. Oa?iaeieia?/i? aei?iaoaaiiy neioaciaaieo niieoe na?ae/aoue i?i
ia?niaeoeai?noue iiooeo na?aae aeine?aeaeoaaieo o?iie?i?a a?ieia?/ii
aeoeaieo ?a/iaei c aenieith aioeieneaeaioiith, iaia?aiinoaa?e?coth/ith,
ae?o?aoe/iith, aioeeiaaoeyioiith oa aioei?e?iaiith ae??th. Aeoiaey/e c
ii??aiyeueii? ioe?iee oa?iaeieia?/ii? aeoeaiino? iaea?eueo aoaeoeaieo
na?aae canoiniao?ieo o iaaee/i?e i?aeoeoe? i?aia?ao?a oa iiaeo
neioaciaaieo niieoe, aeey iiaeeaeaieo oa?iaeieia?/ieo aeine?aeaeaiue
cai?iiiiiaaii 3-iii?e-4-a?ae?iene-2-ienio?iie?i ye iioaioe?eiee
aaiaoii?ioaeoi?iee can?a. ?ic?iaeaii i?iaeo OON ia oeth niieoeo.
7. Anoaiiaeaii ?yae caeiiii??iinoae ca’yceo “no?oeoo?a — ae?y”, ye?
iiaeooue aooe aeei?enoai? aeey oe?eani?yiiaaiiai iiooeo ?a/iaei c
iaia?aiinoaa?e?coth/ith, ae?o?aoe/iith oa aioei?e?iaiith ae??th.
8. Ca ?acoeueoaoaie aei?iaoaaiue aa?a?oeeaeii? oa ooia?oeeaeii?
aeoeaiino? 5-R-1,3,4-o?aae?acie?e-2-ai?ae?a
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio aeyaeaii ?a/iaeie,
aeoeai? ii a?aeiioaiith aei oaeeo caoaeiee?a oai?ia
n?euenueeiainiiaea?nueeeo eoeueoo? ye eenoeiaa ??aea, ie?eeoey??ic ?eno
oa ieyieno?noue eieineiai? eonee ioaieoe?. Iaea?aeai? ?acoeueoaoe
a?aee?eaathoue ia?niaeoeao noai?aiiy ia iniia? aeine?aeaeoaaieo niieoe
iioaioe?eieo ooia?oeeae?a aeey n?euenueeiai ainiiaea?noaa.
Nienie iioae?eiaaieo i?aoeue ca oaiith aeena?oaoe??:
1. 4-Ieneoeiieiiu-2. 15. Neioac -(ie?eaeee-2)-aieaeia
1--4-aeae?iene-2-oeiieii-3-ea?aiiiauo eeneio eae aiciiaeiuo iiauo
ianoa?ieaeiuo i?ioeaiainiaeeoaeueiuo n?aaenoa / E.A.Oe?aeiaoe,
N.A.Oa?ai, I.A.Aaoeoaaaa, A.A.Oo?ia // Oeiey aaoa?ioeeee. niaaeeiaiee. —
1993. — ? 8. — N. 1101-1104.
2. 4-Ieneoeiieiiu-2. 17. Eiiaeainaoeey Ae?eiaia eae oa?ie/anee
aeoeae?iaaiiue i?ioeann / E.A.Oe?aeiaoe, N.A.Oa?ai, I.A.Aacoaeue,
I.A.Aaoeoaaaa // Oeiey aaoa?ioeeee. niaaeeiaiee. — 1993. — ? 9. — N.
1219-1222.
3. 4-Ieneoeiieiiu-2. 19. Iiaue neioac
3-aeeee-2-ieni-4-aeae?ieneoeiieeiia / E.A.Oe?aeiaoe, N.A.Oa?ai,
I.A.Aaoeoaaaa, I.A.Ai?ioiaa, A.A.Oo?ia, E.I.Ai?iieia, I.E.Oeeeiiiiaa //
Oeiey aaoa?ioeeee. niaaeeiaiee. — 1994. — ? 5. — N. 673-678.
4. 4-Ieneoeiieiiu-2. 22. Neioac e aeieiae/aneea naienoaa
1-aeeee(a?ee)-2-ieni-3-ea?ayoiene-4-aeae?ieneoeiieeiia e eo i?iecaiaeiuo
/ E.A.Oe?aeiaoe, I.A.Ai?ioiaa, N.A.Oa?ai, I.A.Aacoaeue, A.A.Oo?ia,
I.A.Ia?onaiei, I.A.Aaoeoaaaa // Oeiey aaoa?ioeeee. niaaeeiaiee. — 1994.
— ? 7. — N. 958-966.
5. 4-Ieneoeiieiiu-2. 26. A?iie?iaaiea 3-caiauaiiuo
2-ieni-4-aeae?ieneoeiieeiia / E.A.Oe?aeiaoe, N.A.Oa?ai, I.A.Aaoeoaaaa,
I.A.Ai?ioiaa, I.E.Oeeeiiiiaa, A.A.Oo?ia // Oeiey aaoa?ioeeee.
niaaeeiaiee. — 1995. — ? 2. — N. 204-207.
6. Neioac e i?ioeaiiee?iaiay aeoeaiinoue
5--1,3,4-oeaaeeacieee-2-aieaeia
1-aeeee-2-ieni-4-aeae?ieneoeiieei-3-ea?aiiiauo eeneio / E.A.Oe?aeiaoe,
N.A.Oa?ai, I.A.Aaoeoaaaa, E.E.Aeeeee, I.E.Oeeeiiiiaa // Oe?aeineay
oa?iaoe. aeaaeaiey, Oa?ueeia, 1994. — 10 n.: Aeaeeia?ao.: 7 iaca. — ?on.
— Aeai. a AIOA Oe?aeiu 10.05.95. — ? 1061-Oe-95
7. Aeieiae/aneea naienoaa 3-aeeee-2-ieni-4-aeae?ieneoeiieeiia /
N.A.Oa?ai, I.A.Aaoeoaaaa, I.A.Ai?ioiaa, E.A.Oe?aeiaoe, E.I.Ai?iieia,
A.I.E?aa/aiei, I.E.Oeeeiiiiaa // Oe?aeineay oa?iaoe. aeaaeaiey,
Oa?ueeia, 1995. — 9 n.: Aeaeeia?ao.: 11 iaca. — ?on. — Aeai. a AIOA
Oe?aeiu 12.07.95. — ? 1806 - Oe-95
?ao?o??aa I.A. “Neioac, o?ceei-o?i?/i? oa a?ieia?/i? aeanoeaino?
3-cai?uaieo 4-a?ae?iene-2-ienio?iie?i?a”. - ?oeiien.
Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa oa?iaoeaaoe/ieo
iaoe ca niaoe?aeuei?noth 15.00.02 - oa?iaoeaaoe/ia o?i?y ?
oa?iaeiaiic?y. - Oe?a?inueea oa?iaoeaaoe/ia aeaaeai?y, Oa?e?a, 1999.
Iaea?aeaii iia? a?ieia?/ii aeoeai? niieoee a ?yae? 3-cai?uaieo
a?ae?iene(ieni)o?iie?i?a: 3-aee?e-4-a?ae?iene-2-ienio?iie?ie oa ?o
4-I-aoeeeuei? iio?aei?; 3-a?ii-3-aee?e-2,4-ae?ienio?iie?ie;
5-R-1,3,4-o?aae?acie?e-2-ai?aee
1-R-4-a?ae?iene-2-ienio?iie?i-3-ea?aiiiaeo eeneio. ?ic?iaeaii
i?aia?aoeai? iaoiaeeee neioaco 3-aee?e-4-a?ae?iene-2-ienio?iie?i?a ?
1-R-3-a?ii-4-a?ae?iene-2-ienio?iie?i?a. Aia?oa iieacaia iiaeeea?noue
cae?eniaiiy eiiaeainaoe?? Ae?eiaia a oiiaao oa?iie?co, yea
a?aeaoaa?oueny ia a?aei?io a?ae eeane/ieo oyaeaiue i?e a?aenooiino?
iniiaieo eaoae?caoi??a; cai?iiiiiaaii eiia??iee iaoai?ci oeueiai
ia?aoai?aiiy. Aea/ai? OO-, ?*- oa II? niaeo?aeuei? oa?aeoa?enoeee
neioaciaaieo ?a/iaei. Ca ?acoeueoaoaie oa?iaeieia?/iiai ne?ei?iao
aeyaeai? aoaeoeai? niieoee iaia?aiinoaa?e?coth/i?, aioeieneaeaioii?,
ae?o?aoe/ii?, aioeeiaaoeyioii? oa ooia?oeeaeii? ae??; anoaiiaeai? ie?ai?
caeiiii??iino? ca’yceo “aoaeiaa — ae?y”. Iaea?eueo ia?niaeoeaia niieoea
?aeiiaiaeiaaia ye iioaioe?eiee aaiaoii?ioaeoi?iee can?a.
Eeth/ia? neiaa: 4-a?ae?iene-2-ienio?iie?i, aee?eaio?ai?eaoe, neioac,
oa?iie?c, aaoa?ioeeee?caoe?y, aaiaoii?ioaeoi?iee can?a.
Aaoeoaaaa I.A. “Neioac, oeceei-oeie/aneea e aeieiae/aneea naienoaa
3-caiauaiieo 4-aeae?iene-2-ienioeiieeiia”. - ?oeiienue.
Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oa?iaoeaaoe/aneeo
iaoe ii niaoeeaeueiinoe 15.00.02 - oa?iaoeaaoe/aneay oeiey e
oa?iaeiaiicey. - Oe?aeineay oa?iaoeaaoe/aneay aeaaeaiey, Oa?ueeia, 1999
a.
Aeenna?oaoeey iinayuaia iieneo iioaioeeaeueiuo eaea?noaaiiuo n?aaenoa a
?yaeo 3-caiauaiiuo 4-aeae?iene-2-ienioeiieeiia. N yoie oeaeueth
inouanoaeai neioac 3-aeeee-4-aeae?iene-2-ienioeiieeiia e eo
4-I-aoeeeueiuo i?iecaiaeiuo; 3-a?ii-3-aeeee-2,4-aeeienioeiieeiia;
5-R-1,3,4-oeaaeeacieee-2-aieaeia
1-R-4-aeae?iene-2-ienioeiieei-3-ea?aiiiauo eeneio. Caaea/a
oniaa?oainoaiaaiey nouanoaothueo iaoiaeia neioaca 3-aeeeecaiauaiiuo
4-aeae?iene-2-ienioeiieeiia auea ?aaeeciaaia a ?acoeueoaoa enneaaeiaaiey
?aaeoeee oeeeeecaoeee yoe?ia 2-ea?aaeeieneiaeiiaieeiauo eeneio. Eae
ieacaeinue, a oneiaeyo oa?iieeca oeacaiiua yoe?u ia?acotho
2-ea?aaeeieneaieeeaeu 4-aeae?iene-2-ienioeiieei-3-ea?aiiiauo eeneio, /oi
aeieacuaaao aiciiaeiinoue inouanoaeaiey eiiaeainaoeee Aeeeiaia, a
ioee/ea io eeanne/aneeo i?aaenoaaeaiee, i?e ionoonoaee iniiaiuo
eaoaeecaoi?ia. Aa?iyoii, aeaiiay ?aaeoeey aeeth/aao noaaeeth
aioo?eiieaeoey?iiai acaeiiaeaenoaey a aiieueiie oi?ia i?iiaaeooi/iiai
N,N-aee-2-ea?aaeeieneaieeeaea iaeiiiaie eeneiou. Eco/aiea aiaeiae/iuo
neiiao?e/iuo aeeaieeeaeia aeeeeiaeiiiauo eeneio iieacaei, /oi a oneiaeyo
oa?iieeca iie ia?acotho niioaaonoaothuea aieeeaeu
3-aeeee-2,4-aeeienioeiieei-3-ea?aiiiauo eeneio, oiaaea eae a i?enoonoaee
iniiaaiee oeeeeecaoeey oeacaiiuo aeeaieeeaeia nii?iaiaeaeaaony
iouaieaieai ea?aaieeeaeiie a?oiie?iaee e i?eaiaeeo e ia?aciaaieth n
aunieeie auoiaeaie 3-aeeee-4-aeae?iene-2-ienioeiieeiia. O/eouaay
i?inoioo neioaca aeeaieeeaeia aeeeeiaeiiiauo eeneio, eioi?ua eaaei
iiaeii iieo/eoue aoeeee?iaaieai aeeeeaio?aieeaoia aeeyoeeiauie yoe?aie
eee aeeoei?aiaeae?eaeaie aeeeeiaeiiiauo eeneio, aeaiiue niinia
?aeiiaiaeiaai a ea/anoaa i?aia?aoeaiiai. ?aoeeiiaeueiia eniieueciaaiea
aeeeeaio?aieeaoia i?e yoii aeinoeaaaony iooai iiaeai?a iaeaieaa
iioeiaeueiiai niioiioaiey ?aaaaioia. Cia/eoaeueii ?anoe?yao aiciiaeiinoe
iaoiaea eniieueciaaiea a ea/anoaa aoeeee?othueo aaaioia aeinooiiuo
aeeoei?aiaeae?eaeia aeeeeiaeiiiauo eeneio, /oi iicaieyao eaaei
neioace?iaaoue eae 1I-3-aeeee-4-aeae?iene-2-ienioeiieeiu, oae e eo
1-caiauaiiua aiaeiae. I?aaeeiaeaiiue niinia neioaca iaoae i?aeoe/aneia
i?eiaiaiea ia oieueei aeey iieo/aiey 3-aeeee-, ii oaeaea e aeey neioaca
ae?oaeo 3-caiauaiiuo 4-aeae?iene-2-ienioeiieeiia. Inouanoaeai neioac
4-I-aoeeeueiuo i?iecaiaeiuo 3-aeeee-4-aeae?iene-2-ienioeiieeiia iooai
aoeeee?iaaiey iineaaeieo aiaeae?eaeaie eee oei?aiaeae?eaeaie ea?aiiiauo
eeneio. Eco/aii iiaaaeaiea 3-aeeee-,
3-ea?aaeeiene-4-aeae?iene-2-ienioeiieeiia e
1-R-2,4-aeeieni-3I-oeiieei-3-ea?aiiiaeo eeneio a oneiaeyo a?iie?iaaiey
iieaeoey?iui a?iiii. Onoaiiaeaii, /oi a?iie?iaaiea
1-R-2,4-aeeieni-3I-oeiieei-3-ea?aiiiauo eeneio ni?iaiaeaeaaony eo
aeaea?aieneee?iaaieai, /oi aeaao aiciiaeiinoue ?aeiiaiaeiaaoue aeaiiue
iaoiae a ea/anoaa i?aia?aoeaiiai aeey iieo/aiey
1-R-3-a?ii-4-aeae?iene-2-ienioeiieeiia. Oa?iieecii yoeeiauo yoe?ia
1-R-4-aeae?iene-2-ienioeiieei-3-ea?aiiiauo eeneio e
2-aieii-5-R-1,3,4-oeaaeeacieia iieo/aiu niioaaonaothuea aieaeu,
iauaaeeiythuea a naiae no?oeoo?a aeaa oa?iaeioi?a. Anaai neioace?iaaii
71 ia iienaiiia a eeoa?aoo?a i?iecaiaeiia oeiieeia, no?oeoo?a e
eiaeeaeaeoaeueiinoue eioi?uo iiaeoaa?aeaeaiu iaoiaeaie OO-, EE- e
II?-niaeo?ineiiee, aeaiiuie yeaiaioiiai aiaeeca e oiieineieiie
o?iiaoia?aoee, a ?yaea neo/aaa - ano?a/iui neioacii. I?iaaaeai
aeieiae/aneee ne?eieia iieo/aiiuo aauanoa ia auyaeaiea aioeieneaeaioiie,
iaia?aiinoaaeeece?othuae, aioeoe?aieaeiie, aeeo?aoe/aneie,
i?ioeaiainiaeeoaeueiie, aioeiee?iaiie, aioeeiaaoeyioiie, aioe-AE*,
i?ioeai?aeiaie, aa?aeoeeaeiie e ooiaeoeeaeiie aeoeaiinoe. Ii
?acoeueoaoai enneaaeiaaiey aeieiae/aneie aeoeaiinoe auyaeaiu yooaeoeaiua
niaaeeiaiey iaia?aiinoaaeeece?othuaai, aioeieneaeaioiiai,
aeeo?aoe/aneiai e aioeeiaaoeyioiiai aeaenoaey; onoaiiaeaiu ioaeaeueiua
caeiiiia?iinoe nayce “no?oeoo?a aeaenoaea”. Iieacaia ia?niaeoeaa
nicaeaiey ia iniiaa 5-R-1,3,4-oeaaeeacieee-2-aieaeia
1-R-4-aeae?iene-2-ienioeiieei-3-ea?aiiiauo eeneio iioaioeeaeueiuo
ooiaeoeeaeia aeey ai?ueau n a?aaeeoaeyie naeueneioicyenoaaiiuo eoeueoo?.
A ea/anoaa ia?niaeoeaiiai aaiaoii?ioaeoi?iiai n?aaenoaa i?aaeeiaeai
3-iiiee-4-aeae?iene-2-ienioeiieei, aeey eioi?iai ?ac?aaioai i?iaeo
a?aiaiiie oa?iaeiiaeiie noaouee.
Eeth/aaua neiaa: 4-aeae?iene-2-ienioeiieei, aeeeeaio?aieeaou, neioac,
oa?iieec, aaoa?ioeeeeecaoeey, aaiaoii?ioaeoi?iia n?aaenoai.
Evtifeeva O.A. The synthesis, physico-chemical and biological
properties of 3-substituted-4-hydroxy-2-oxoquinolines. - Manuscript.
The thesis for the Master Degree of Pharmacy in Speciality 15.00.02 -
Pharmaceutical Chemistry and Pharmacognosy. - Ukrainian Academy of
Pharmacy, Kharkov, 1999.
New biologically active substances - 3-alkyl-4-hydroxy-2-oxoquinolines
and their 4-O-acylderivatives; 3-bromosubstituted-2,4-dioxoquinolines;
5-R-1,3,4-thidiazolyl-2-amides 1-R-4-hydroxy-2-oxoquinolines of
3-carboxylic acids - have been studied in the range of 3-substituted
hydroxy(oxo)quinolines. The synthetic preparative methods for
3-alkyl-4-hydroxy-2-oxoquinolines and
1-R-3-brom-4-hydroxy-2-oxoquinolines have been developed. For the first
time the possibility of the Dickman condensation realization was shown
under thermolysis conditions. Unlike the classic conditions it is
carried out in the absence of the basic catalysts. So the possible
mechanism of this transformation has been suggested. UV-, IR-,
PMR-spectra characteristics of the compounds synthesized have been
studied. During the pharmacological screening effective substances with
membranostabilizing, antioxidant, diuretic, anticoagulant and fungicidic
activities have been revealed and some regularities of the
“structure-action” relation have been established. The most perspective
compound has been recommended as a potential hepatoprotective agent.
Key words: 4-hydroxy-2-oxoquinoline, alkylanthranilates, synthesis,
thermolysis, heterocyclisation, hepatoprotective agent.
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