IAOeIIIAEUeIA AEAAeAIIss IAOE OE?A?IE
IINOEOOO AIII?AAII*II? OIII? OA IAOOIOIII?
IAIssIEE Noaiai Na?a?eiae/
OAeE 547.853.85:541.67
CEIOAC AE?EICEAeIEO OA INAAAeIAE?EICEAeIEO
IIO?AeIEO 6-ACAO?AOeEEO OA 6-ACAOeEOICEIO
02.00.10 – A?ii?aai?/ia o?i?y
Aaoi?aoa?ao aeena?oaoe??
ia caeiaoooy iaoeiaiai nooiaiy
eaiaeeaeaoa o?i?/ieo iaoe
Ee?a – 1999
Aeena?oaoe??th ? ?oeiien
?iaioa aeeiiaia a ?inoeooo? iieaeoey?ii? a?ieia?? oa aaiaoeee IAI
Oe?a?ie
Iaoeiaee ea??aiee
eaiaeeaeao o?i?/ieo iaoe
Oaeaiae Aiaoie?e Naaanoueyiiae/
Iaoeiai-ae?iaie/ee oeaio? “Ai?uaa?anueeee o?i?ei-oa?iaoeaaoe/iee caaiae”
cano. aai. aee?aeoi?a c iaoeiaeo ieoaiue
Io?oe?ei? iiiiaioe:
aeieoi? a?ieia?/ieo iaoe, i?ioani?
I??ioie/aiei Ieeiea Noaiaiiae/
Ee?anueeee aea?aeoi?aa?neoao ?i. Oa?ana Oaa/aiea
caa?aeoaa/ eaoaae?e a?io?ceee
eaiaeeaeao o?i?/ieo iaoe
I?eeac/eeiaa Ethaeieea Iao??aia
?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie
a.i. i?ia?aeiiai iaoeiaiai ni?a?ia?oieea a?aeae?eo o?i?? a?iaeoeaieo
acioai?nieo aaoa?ioeeee?/ieo iniia
I?ia?aeia onoaiiaa:
?inoeooo i?aai?/ii? o?i?? IAI Oe?a?ie
a?aeae?e o?i?? a?ieia?/ii aeoeaieo ?a/iaei, i. Ee?a
Caoeno a?aeaoaeaoueny “ 28 ” o?aaiy 1999 ?. i 1000 aiaeei? ia can?aeaii?
niaoe?ae?ciaaii? a/aii? ?aaee Ae 26.220.01 a ?inoeooo? a?ii?aai?/ii?
o?i?? oa iaooio?i?? IAI Oe?a?ie (253660, Ee?a, aoe. Io?iainueea, 1)
C aeena?oaoe??th iiaeia iciaeiieoenue o a?ae?ioaoe? ?inoeoooo
a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie (253660, Ee?a, aoe.
Io?iainueea, 1)
Aaoi?aoa?ao ?ic?neaiee “28” ea?oiy 1999 ?.
A/aiee nae?aoa?
niaoe?ae?ciaaii? a/aii? ?aaee Ae.I.Oaaei?ye
CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE
Aeooaeuei?noue oaie. Neioaoe/i? ioeeaiceaee oa ?o aiaeiae caeaaia
aeeeeeathoue i?aeaeuaiee ?ioa?an. Ii-ia?oa, niieoee aeaiiai eeano
iaiao?aei? aeey aeine?aeaeaiiy ooiaeaiaioaeueieo i?iaeai iieaeoey?ii?
a?ieia?? oa iaaeeoeeie, aea aiie ciaeoee oe?iea canoinoaaiiy ye
iiaeaeuei? ?a/iaeie, no?oeoo?ii aeecuee? aei i?e?iaeieo iaoaaie?o?a
ioeea?iiaiai iai?io. C ?ioiai aieo, aiiiaeuei? ioeeaiceaee i?eaa?oathoue
oaaao ye aoaeoeai? o?i?ioa?aiaaoe/i? i?aia?aoe, aeoeai?noue yeeo
coiiaeaia caeaoi?noth aieeaaoe ia i?ioeane a?ineioaco oa
a?io?ainoi?iaoe?? ioeea?iiaeo eeneio.
N1-ae?eiceaee cai?uaieo 6-acai??ei?aeei?a ? no?oeoo?ieie aiaeiaaie
ioeeaiceae?a i??ei?aeeiiaiai ?yaeo, ui a?ae??ciythoueny a?ae i?e?iaeieo
cai?iith a aae?eii? NI-a?oie ia aoii acioo. Oe? niieoee ia o?eueee
oni?oii canoiniaothoueny ye iiaeaeuei? noano?aoe o aea/aii? i?ioean?a
iaoaaie?cio ioeea?iiaeo eeneio, – aeaye? c ieo (iai?eeeaae,
6-acao?eaeei, 6-acaoeeoeaeei) oe?iei aeei?enoiaothoueny a iaaeeoeei? ye
aioei?e?iai?, i?ioea??oni?, i?ioeiooeeii? i?aia?aoe. Iiaee ?iioeuen
aea/aiith acaioeeaiceae?a iaaeaei anoaiiaeaiiy ?ioiiiiaeoethth/i?
aeoeaiino? 6-acaoeeoeaeeio, iaoa?aeoa?ii? aeey ioeeaiceaeieo
i?aia?ao?a. A?aoiaoth/e i/aaeaeio ia?niaeoeai?noue iiooeo iiaeo
oa?aiaaoe/ieo cania?a na?aae acai??ei?aeeiiaeo ioeeaiceae?a oa ?o
aiaeia?a, aino?iaeooaeueiith ? ?ic?iaea aoaeoeaieo iaoiae?a o?i?/iiai
neioaco niieoe aeaiiai eeano.
Iaoa ? caaea/? aeine?aeaeaiiy. Iaoith ?iaioe ? ?ic?iaea iaoiae?a
neioaco iiaeo ioeeaiceaeieo iio?aeieo 6-acai??ei?aeei?a oa ?o
aoeeee?/ieo aiaeia?a. O ca’yceo c oeei aoei iaiao?aeii:
aea/eoe ae?eiceethaaiiy aee?eueiaaieo 5-cai?uaieo 6-acai??ei?aeei?a oa
?o o?iaiaeia?a, a ia?oo /a?ao 5-ai?iieeneioieo iio?aeieo
acai??ei?aeeiiaeo ioeeaiceae?a;
aeine?aeeoe ??ci? i?aeoiaee aei neioaco iaae?eiceaeieo aiaeia?a a?aeiieo
o?eaceiiaeo ioeeaiceae?a (6-acao?eaeeio oa 6-acaoeeoeaeeio);
i?iaanoe eiiieaenia aea/aiiy no?oeoo?e, o?i?/ieo oa a?ieia?/ieo
aeanoeainoae neioaciaaieo 6-acai??ei?aeeiiaeo ioeeaiceae?a oa ?o
aoeeee?/ieo aiaeia?a.
Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. Aia?oa a i?ioean?
ae?eiceethaaiiy oa aee?ethaaiiy iio?aeieo 6-acai??ei?aeei?a iaoiaeii
“nee?eueii? eiiaeainaoe??” aeei?enoaii iaeii/anio aeoeaaoe?th aae?eiia
oa ae?eiceaeiiai eiiiiiaioa, ui iaoiaee/ii aea? ciiao ia’?aeiaiiy
i?ioean?a nee?ethaaiiy oa aee?eoaaiiy. Oaea iaeiinoaae?eia noaia c
oni?oii aoea ?aae?ciaaia ye a neioacao ae?eiceae?a 6-acai??ei?aeei?a,
oae ? a neioacao aoeeee?/ieo iio?aeieo 6-acaoeeoeaeeio. Cai?iiiiiaaii
iiaee i?aeo?ae aei iaea?aeaiiy 5-aee?eai?iiiio?aeieo 6-acai??ei?aeei?a –
aaoa?ioeeee?/ieo eiiiiiaio?a ioeeaiceaeiiai neioaco.
Oai?aoe/ia oa i?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a. Aea/aii
caeiiii??iino? ae?eiceethaaiiy oa aee?ethaaiiy cai?uaieo
6-acai??ei?aeeiiaeo iniia a oiiaao iaeiinoaae?eiiai aa??aioo nee?eueiiai
iaoiaeo neioaco ioeeaiceae?a. Aeyaeaii a?aei?iiino? a iaoai?ciao
aca?iiae?? aae?eiia c aoaeaaiaeiei oa iaaoaeaaiaeiei eiiiiiaioii, ui a
inoaiiueiio aeiaaeeo aaaea aei ao?aoe ?aa?iniaoeeo?/iino? ?aaeoe??
ae?eiceethaaiiy. Aecia/aii aieea N5-aee?eai?iicai?niee?a
6-acai??ei?aeei?a ia ?aaeoe?eio caeaoi?noue aaoa?ioeeee?a o ?aaeoe?yo c
ia?aoeeeueiaaieie aoaeaaiaeaie. Iieacaii, ui N5-aee?eai?iicai?nieee
nooo?ai cieaeothoue ?aaeoe?eio caeaoi?noue iieiaeaiiy N4 ii
a?aeiioaiith aei ioeeaio?eueieo ?aaaaio?a, ui aeicaiey? i?iaiaeeoe
naeaeoeaia cai?uaiiy a iieiaeaii? N2 o?eaceiiaiai e?eueoey. Ia iniia?
io?eiaieo aeaieo ?ic?iaeaii i?aia?aoeaio noaio io?eiaiiy N1-ae?eiceae?a
cai?uaieo 6-acai??ei?aeeiii?a oa 6-acai??ei?aeeio?ii?a. Io?eiaii iaoaio
Oe?a?ie N1785 ia niin?a io?eiaiiy 6-acaoeeoeaeeio – oa?aiaaoe/iiai
i?aia?aoo oe?ieiai niaeo?o ae??.
Iniaenoee aianie aeena?oaioa. Aenia?eiaioaeueia /anoeia ?iaioe, aiae?c
niaeo?aeueieo aeaieo oa anoaiiaeaiiy no?oeoo?e neioaciaaieo niieoe
aeeiiai? iniaenoi aeena?oaioii. Iioae?eiaai? ?acii ?c ni?aaaoi?aie
iaoa??aee, ui aa?eoee aei aeena?oaoe??, iaea?aeai? ca aaciina?aaeiueith
o/anoth aeena?oaioa.
Ai?iaaoe?y ?acoeueoao?a aeena?oaoe??. Iniiai? ?acoeueoaoe ?iaioe aoee
i?aaenoaaeai? ia eiioa?aioe?yo iieiaeeo o/aieo (Eeoei?a, 1986; ?eaa,
1989), i?aeia?iaeiiio neiiic?oi? ii aioea??onieo i?aia?aoao (?eaa,
1989), ia eiioa?aioe?? ii o?i?? i?e?iaeieo niieoe (?eaa, 1990), XVII
oe?a?inuee?e eiioa?aioe?? c i?aai?/ii? o?i?? (Oa?e?a, 1995).
Ioae?eaoe??. Ca iaoa??aeaie ?iaioe iioae?eiaaii 10 i?aoeue, c ieo 4
noaoo? a iaoeiaeo oaoiaeo aeo?iaeao, oace 5 aeiiia?aeae, io?eiaii iaoaio
Oe?a?ie N1785.
No?oeoo?a oa ianya aeena?oaoe??. Aeena?oaoe?y neeaaea?oueny ?c anooio
(?icae?e I), iaeyaeo e?oa?aoo?e (?icae?e II), iaaiai?aiiy ?acoeueoao?a
(?icae?ee III-IV), aenia?eiaioaeueii? /anoeie (?icae?e V), aeniiae?a oa
nieneo e?oa?aoo?e, ui i?noeoue 130 iaeiaioaaiue. ?iaioa aeeth/a? 18 noai
oa 13 oaaeeoeue. Caaaeueiee ianya aeena?oaoe?? -131 noi?.
INIIAIEE CI?NO ?IAIOE
“Nee?eueia eiiaeainaoe?y” a neioac? N-ae?eiceae?a 5-cai?uaieo
6-acao?aoeee?a
Iniiaiith noaae??th neioaco ioeeaiceae?a iaoiaeii “nee?eueii?
eiiaeainaoe??” ? aca?iiae?y nee?eueiaaieo aaoa?ioeeee?/ieo iniia c
a?aeiia?aeieie iio?aeieie aoaeaaiae?a, iae/ano?oa ia?aoeeeueieie, a
i?enooiino? iaaieo eaoae?caoi??a. 5-Ea?aieneaee?eai?iiiio?aei?
acai??ei?aeei?a eaaei nee?ethaaeenue noi?ooth aaenaiaoeeaeeneeacaio
(AIAeN) oa o?eiaoeeoei?neeaio (OION). Iieacaii, ui 2-o?iiio?aei?
6-acai??ei?aeei?a nee?ethaaeenue aaea?/? oaeaeoa ?o ieniaiaeia?a.
5-Ea?aieneaee?eai?ii-6-acai??ei?aeeiia? ioeeaiceaee iaea?aeoaaee ca
aeiiiiiaith eiiaeainaoe?? o?eiaoeenee?eueieo anoa??a aaoa?ioeeee?/ieo
iniia c ia?aoeeeueiaaieie aoaeaaiaeaie a 1,2-aeeoei?aoai? a i?enooiino?
oao?aoei?eaeo ieiaa i?e e?iiaoi?e oaiia?aoo?? (?en. 1).
?en. 1
Aea/aii aieea ??cieo oaeoi??a ia i?ioean eiiaeainaoe??. Iieacaii, ui
ii?yae c aeaeo?iiiith i?e?iaeith aaoa?ioeeee?/ii? iniiae, aoaeiaa
aoaeaaiaeiiai eiiiiiaioa iicia/a?oueny ia aeoiae? i?iaeoeo?a ?aaeoe??
ae?eiceethaaiiy. Oae, N1-?eaioo?aiiceaee 5-cai?uaieo 6-acao?aoeee?a aoei
iaea?aeaii c a?eueoeie aeoiaeaie (85-87%), i?ae a?aeiia?aei? aethei-,
a?aa?ii- oa eneeii??aiiceaee. I?e?iaea aoeeeueieo caoenieo a?oi i?e
a?ae?ieneeao aoaeaaiaeiiai eiiiiiaioa oaae aieeaa? ia ooai?aiiy
aoeeeioeeaiceae?a. Iai?eeeaae, aeu? aeoiaee o?eaaiciao?a
?eaioo?aiiceae?a ii??aiyii c aeoiaeaie o?eaoeaoeeueieo iio?aeieo
iiaeooue iiynithaaoenue a?eueoith noaa?euei?noth aoeeeienii?eiaiai
eao?iia, ooai?aiiai ca o/anoth 2′-I-aaici?eueii? a?oie ?eaice.
Anoaiiaeaii, ui nooo?aee aieea ia oa?aeoa? i?io?eaiiy “nee?eueii?
eiiaeainaoe??” oa aeo?ae ?? i?iaeoeo?a ia? iiey?ia ni?aa?aeiioaiiy
eaoae?caoi?a oa ia?aoeeeueiaaiiai aoaeaaiaeo (n). Iioeiaeueieie iiaeia
aaaaeaoe cia/aiiy n aeecuee? 0,7, oi/a canoinoaaiiy a?eueoi? e?eueeino?
eaoae?caoi?a a aeayeeo aeiaaeeao ? iaiao?aeiei, iniaeeai o aeiaaeeo
ooai?aiiy aeinoaoiuei noaa?eueieo (-eiiieaen?a i?ae eaoae?caoi?ii oa
nee?eueiaaiith iniiaith. I?e ae?eiceethaaii? iaoeeiaiai oa aooeeiaiai
anoa??a 5-ea?aieneiaoeeai?ii-6-acao?aoeeeo aoei iieacaii, ui
eaa?euei?noue neeaaeiianoa?ii? a?oie a oiiaao “nee?eueii? eiiaeainaoe??”
i?eaiaeeoue aei ooai?aiiy noi?o? ae?eiceae?a. Iaa?oue i?e iaaenie?e
eiioeaio?aoe?? oao?aoei?eaeo ieiaa a iaaaeee?e e?eueeino? ooai?ththoueny
aoeeeioeeaiceaee c iieeaiith anoa?iith a?oiith. I?iaaaeaiiy
eiiaeainaoe?? a i?enooiino? iieueii? aeie? eaoae?caoi?a, ui ia?aaeuo?
iaeeieoeth, iaeii?eeiyoia aeey io?eiaiiy i?iaeoeo?a c? neeaaeiianoa?iith
ooieoe??th. C ?ioiai aieo, oaeee iapaaia paaeoei? aea? iiaeeeainoue
iopeioaaoe ioeeaiceae c aieueiith eapaieneeueiith ooieoei?th, ui ?ieiee
ia? i?eioeeiiaa cia/aiiy. Oae, iaea?aeaiiy ioeeaiceae?a
5-ea?aieneiaoeeaiiii-6-acao?aoeeeo oeyoii ae?eiceethaaiiy aaoa?ioeeeeo
iaiiaeeeaa aianeiaeie poeioaaiiy inoaiiueiai iiae /an noaaei?
neeiethaaiiy. Iaeiae oea eaaei iiaeia aeinyae a oiiaao eiiaeainaoe?? c
a?aeiia?aeiei anoa?ii c iaeii/aniei iieeaiiyi i?iaeoeoa (?en. 2).
?en. 2
Oeieaai aiaecia/eoe, ui ipe aeieiceethaaiii
2-o?i-5-ea?aieneaee?eai?ii-6-acao?aoeeeo oa eiai iioiaeieo a oiiaao
“neeieueii? eiiaeainaoei?” picpeao neeaaeiianoa?iiai oapoioaaiiy ia
niinoapiaaeinue. Iiaeia ipeionoeoe, ui a cacia/aieo niieoeao
noaaieueiinoue eapaiaoieneeueieo apoi caaacia/o?oueny aeaeopiiiei
aieeaii aoiio nipee a ae?oaiio iieiaeaiii aaoapioeeeei/iiai caeeoeo.
E??i oiai, ne?ae a?aecia/eoe oaeiae, ui eiiaeainaoe?y nee?eueiaaieo
2-o?iiio?aeieo c aoaeaaiaeieie eiiiiiaioaie a?aeaoaa?oueny cia/ii
oaeaeoa, i?ae aeey acai??ei?aeeiae?ii?a. Oea ca’ycaii c i?aeaeuaiiyi
ioeeaio?eueiino? N1-aoiia i?e cai?i? aoiia eenith a iieiaeaii? N2
aaoa?ioeeeeo ia iaio aeaeo?iiaaaoeaio n??eo. Ei?iooee /an i?iaaaeaiiy
?aaeoe?? oaeiae ni?eya caa?aaeaiith neeaaeiianoa?ii? ooieoe??.
Aaeeeee ?ioa?an aeeeeeaei i?iaaaeaiiy eiiaeainaoe?? cai?uaieo
6-acai??ei?aeei?a a oiiaao ni?iuaiiai iaeiinoaae?eiiai aa??aioo
“nee?eueii? eiiaeainaoe??” (?en. 3). Noi?uaiiy i?ioean?a io?eiaiiy
nee?eueieo anoa??a oa aca?iiae?? inoaii?o c ia?aoeeeueiaaieie
aoaeaaiaeaie a i?enooiino? SnCl4 aeaei ciiao nooo?ai ni?inoeoe i?ioean
ae?eiceethaaiiy oa nei?ioeoe caaaeueiee /an neioaco ioeeaiceae?a aac
cieaeaiiy ?o aeoiaeo.
Aeey i?iaaaeaiiy eiiaeainaoe?? aei a?aeiia?aeiiai 5-cai?uaiiai
aaoa?ioeeeea a aaniethoiiio ?ic/eiieeo aeiaeaaaee aea?iiey?i? e?eueeino?
AIAeN, OION, aoeeeueiaaiiai aoaeaaiaeo oa SnCl4. Eaoae?caoi? a oeeo
oiiaao ii/eia? aeeiioaaoe nai? ooieoe?? eeoa i?e 20% iaaeeeoeo a?aeiinii
aaoa?ioeeeeo. Eiia??ii, oea ca’ycaii c ooai?aiiyi (-eiiieaeno SnCl4 c
iniiaith. Aoei anoaiiaeaii, ui iioeiaeueiei ? ni?aa?aeiioaiiy 1,4 aea.
eaoae?caoi?a a?aeiinii aaoa?ioeeeeo. *an i?iaaaeaiiy aeania ?aaeoe??
eiiaeainaoe?? aoa oaeei aea, ye ? o aeainoaae?eiiio aa??aio? nee?eueiiai
iaoiaeo, iaeiae aeeeth/aiiy iiia?aaeiuei? noaae?? nee?ethaaiiy
aaoa?ioeeee?a aeaei ciiao nei?ioeoe caaaeueio o?eaae?noue i?ioeano
io?eiaiiy ioeeaiceae?a a?eueo i?ae aaea?/?.
?en. 3
A oeeo oiiaao 2-oii-5-ea?aieneaee?eai?iiiioiaeii 6-acao?aoeeeo paaaoaaee
c iapaoeeeueiaaieie aoaeaaiaeaie c aenieei aeoiaeii (>90%), i?e/iio
opeaaeinoue paaeoei? ia iapaaeuoaaea 30-45 oa.
Iaipaaeaiinoue aeieiceethaaiiy 5-cai?uaieo acai??ei?aeei?a, oiaoi N1- /e
N3-aeieiceaeio ipepiaeo iopeiaieo 6-acaioeeaiceaeia anoaiiaethaaee ia
iniiai iipiaiyeueiiai aea/aiiy OO-niaeopia N-aeieiceeueieo, N1- oa
N3-iaoeeueieo iioiaeieo, a oaeiae niaeo??a aeo?aeieo aaoa?ioeeee?a.
A OO-niaeo?ao aeo?aeieo iniia oa io?eiaieo ioeeaiceae?a i?e ??cieo
cia/aiiyo pH na?aaeiaeua ye o a?oi? ieni-, oae ? o?ii??ei?aeei?a
niinoa??aaeanue /?oea ei?aeyoe?y ye c e?oa?aoo?ieie aeaieie aeey N1- /e
N3-iio?aeieo, oae ? c? niaeo?aie iiaeaeueieo niieoe – N1- oa
N3-iaoeeueieo iio?aeieo 6-acai??ei?aeei?a. Oaeei /eiii, caaaeyee aeaiei
OO-niaeopia acai??ei?aeei?a oa ?o iioiaeieo aaeaeinue aeiaanoe
N1-aeieiceaeio aoaeiao 5-cai?uaieo 6-acaioeeaiceaeia.
Ca aeiiiiiaith niaeopia II? aoea anoaiiaeaia (-aiiiapia aoaeiaa
N-aeieiceaeia 6-acai??ei?aeei?a oa ?o 5-caiiuaieo iioiaeieo.
Io?eiaiiy 6-acaoeeoeaeeio oa eiai iio?aeieo a oiiaao ni?iuaiiai aa??aioo
“nee?eueii? eiiaeainaoe??”
6-Acaoeeoeaeei a?aeiiee ye aeoeaiee i?ioeiooeeiiee oa i?ioea??oniee
i?aia?ao. Cia/iee iaoeiaee oa i?aeoe/iee ?ioa?an aeeeeeaei aea/aiiy
iiaeeeaino? aeei?enoaiiy aeey eiai neioaco iaeiinoaae?eiiai aa??aioo
iaoiaeo “nee?eueii? eiiaeainaoe??”.
?ic?iaeaiee iaie i?aeo?ae (?en. 4) aaco?oueny ia eiiaeainaoe??
4-o?i-6-acao?aoeeeo 1a c oao?aaoeaoaoii ?eaice a i?enooiino?
nee?ethth/eo aaaio?a oa SnCl4 ye eaoae?caoi?a a oiiaao ni?iuaiiai
aa??aioo nee?eueiiai iaoiaeo ioeeaiceaeiiai neioaco. ?aaeoe?th
i?iaiaeeee a aaniethoiiio aoeaoii?o?ee? a i?enooiino? 1,2-1,4 aea SnCl4
a?aeiinii aaoa?ioeeeeo.
Iopeiaiee opeaoeaoao 4-oii-6-acaopeaeeio 2a aeae? aaiaeeee a ?aaeoe?th c
aiiaeii a aoaiiei, aea iaeii/anii a?aeaoaaeinue aiiioaaiiy oiiapoie oa
a?aeuaieaiiy eaa?eueieo aoeaoeeueieo caoenieo a?oi a i’yeeo oiiaao.
?en. 4
Aeoiae 6-acaoeeoeaeeio 3a neeaaeaa 65-76% a picpaooieo ia
4-oii-6-acaopaoeee 1a. Inoaii?e ? aeinooiiith pa/iaeiith, yeo
iopeiothoue c i?aeoe/ii e?euee?niei (98%) aeoiaeii c iipiaiyii aeaoaaeo
6-acaopaoeeeo oa iaioanoeueoiaeo oinoipo oeyoii eei’yo?iiy ?o a
ae?ienai?. Iiae?aiei /eiii, aeoiaey/e c 4-oii-5-iaoee-6-acaopaoeeeo 1b,
aoa iopeiaiee 5-iaoee-6-acaoeeoeaeei 3b c aeoiaeii 66%. ?ic?iaeaiee iaie
niin?a iaea?aeaiiy acaoeeoeaeeio caoeuaiee iaoaioii Oe?a?ie.
Iaea?aeaiiy aoeeee?/ieo aiaeia?a 6-acai??ei?aeeiiaeo ioeeaiceae?a
Aoeeeei/i? aiaeiae ioeeaiceaeia – oea ieneaee?euei? iioiaeii
i??ei?aeeiiaeo aaoa?ioeeee?a, a yeeo aoaeaaiaeiee opaaiaio caiiiaii
eiioi?iaoe?eii eaa?eueieie nopoeoopieie aeaiaioaie, ui i?noyoue
piciieiooee oopaiiciee caeeoie /e o?aaiaio, yeee ?i?oo? eiai aoaeiao.
Aeae?eythoue ope iniiaieo oeie ieneaee?eueieo iioiaeieo, yei iiaeia
piciinoeoe a iipyaeeo c?inoath/i? opainoipiaoei? aoaeaaiaeiiai caeeoeo,
a naia: aiaeiae c picuaieaiei ca’yceii N2′-N3′ a peaioopaiiciiio
o?aaiaio? oa niieoee c aiaeuaieaieie N2′- aai/i N3′-ieneiaoeeueieie
apoiaie:
Na?aae aoeeee?/ieo ioeeaiceae?a ciaeaeaii aoaeoeai? aioea??oni?
i?aia?aoe, iai?eeeaae, aoeeeeia??. Aeioe?eueiei aoa oaeiae iiooe
a?ieia?/ii aeoeaieo i?aia?ao?a na?aae aoeeee?/ieo aiaeia?a
6-acai??ei?aeeiiaeo ioeeaiceae?a. Iaie ?ic?iaeaii e?eueea iaoiae?a
iaea?aeaiiy o?ueio aeuaaeacaieo inaaaeiae?eiceaeieo iio?aeieo
6-acai??ei?aeei?a.
A) Neioac naei-iio?aeieo oa R- oa S-aiaio?iia??a aoeeee?/ieo aiaeia?a
oeyoii ia?eiaeaoiiai ieeneaiiy 6-acai??ei?aeeiiaeo ioeeaiceae?a.
A ?acoeueoao? ?aaeoe?? “nee?eueii? eiiaeainaoe??” aoee iaea?aeai?
?eaiioeeaiceaee 6-acaoeeoiceio oa 5-iaoee-6-acaoeeoiceio, ye? a oiiaao
ia?eiaeaoiiai ieeneaiiy c iiaeaeueoei a?aeiiaeaiiyi ae?aeueaeaa?ae?a 5a
oa 5b aoee ia?aoai?ai? a naei-iio?aei? ne?aeoth/ei niiniaii (?en. 5)
?en. 5
Ieeneaiiy ?eaiceae?a 4a oa 4b cae?enithaaee ca aeiiiiiaith ia?eiaeaoo
iao??th o aiaeiiio na?aaeiaeu?. I?ioean ieeneaiiy ca’yceo C2′ -C3′ a
?eaiceaeao i?ioiaeeoue ye?nii oa oaeaeei (30 oa a i?enooiino? 1 aea.
NaIO4). Ia?iaea i?iaeoeoo ai?a?ae?eaeii iao??th i?eaiaeeoue aei
a?aeiiaeaiiy aeueaeaa?aeieo a?oi o nie?oia?. Oaeei /eiii iaea?aeaii
naei-ioeeaiceaee 6a oa 6b, ui i?noyoue ?icuaieaiee ca’ycie C2′ -C3′.
Aoeeeei/ii iioiaeii c aiaeuaieaiei 3′-ieneiaoeeueiei opaaiaioii a
oopaiiciiio oeeeei – 1′,5′-aeiiene-3′-ienaiaioeeueii iioiaeii
ioeeaiceaeia – iaeiaea/aiee eean niieoe ? o aeiaaeeo acai??ei?aeei?a
?ai?oa ia aoee iaea?aeai?. Ipe/eiith oeueiai, a ia?oo /a?ao, ?
neeaaei?noue ?o neioaco oeyoii aee?ethaaiiy iniia. O aeiaaeeo
aaciina?aaeiuei aee?ethaaiiy iio?aeieo 6-acao?aoeeeo a?aeiia?aeieie
aaeiaaiai?nieie neioiiaie i?iaeoeoaie iiaea aooe noi?o N1- oa
N3-iio?aeieo, aea, ye i?aaeei, i?a ia?aaaaeaoe N3-?ciia?. I?e oeueiio
aeoiaeii inaaaeiaeieiceaeii neioiie iaeapaeothoueny ii aaaaoinoaaeieiie
noaii, a iiaeaeueoa aeeieoaaiiy neeieueiaaieo aaoapioeeeeia oaeeie
?aaaaioaie iaia’yceiai aaaea aei ooaipaiiy noi?o? R- i S-aiaioiiiap?a
aoeeee?/ieo aiaeiaia ioeeaiceaeia. Oiio, ia iao iiaeyae, ia?niaeoeaiei
i?a aooe neioac niieoe oeueiai eeano oeyoii ia?eiaeaoiiai ieeneaiiy oa
ianooiiiai a?aeiiaeaiiy ioeeaiceae?a. I?e oeueiio ia o?eueee cia/ii
ni?iuoaaany oa i?enei?thaaany aanue i?ioean neioaco, a e noaaaei
iiaeeeaei io?eiaiiy ?iaeea?aeoaeueieo aiaio?iia??a, ine?eueee a neioac?
aeei?enoiaothoueny aeo?aei? eiie?aoi? aiiia?e ioeeaiceae?a, a i?ioean
ieeneaiiy-a?aeiiaeaiiy ia aieeaa? ia eiio?ao?aoe?th ae?eiceaeiiai
ca’yceo.
A iniiao iaoiaeo iaeapaeaiiy aoeeee?/ieo aiaeia?a 6-acaiipeiiaeeiia c
a?aeuaieaiei o?aaiaioii C3′ aoea iieeaaeaia aeainoaaeieia noaia neioaco.
O aiaeiiaiaeiinoi c iath, ia iapoie noaaei? aoee neioaciaai? iio??ai?
ioeeaiceaee – (-D-eneei- oa (-L-apaaiiiiipaiiceaee 6-acaiipeiiaeeiia – a
oiiaao “nee?eueii? eiiaeainaoe??”. Ianooiia noaaeiy aeeth/aea
iapeiaeaoia ieeneaiiy iipaiiceaeia aei aiaeiiaiaeieo ae?aeueaeaaiae?a oa
iiaeaeueoa ?o aiaeiiaeaiiy aipaiaepeaeii iao??th (?en. 6).
?en. 6
Aea/aiiy paaeoeie ieeneaiiy iipaiiceaeia i aiaeiiaeaiiy
ae?aeueaeaaiaeieo iioiaeieo aeicaieeei iiae?a?aoe iioeiaeuei? oiiae
ipiaaaeaiiy oeeo opainoipiaoeie ioeeaiceaeia. Aeey iiaiiai ieeneaiiy
iipaiiceaeo c a?aeuaieaiiyi C3′-o?aaiaioo iaiaoiaeii aaiaeeoe a
paaeoeith 2-epaoiee iaaeeeoie iapeiaeaoo iaopith. Ne?ae a?aecia/eoe, ui
i?ioean ieeneaiiy eneei- oa a?aa?iiae?eiceae?a a?aeaoaa?oueny cia/ii
iia?euei?oa, i?ae ?eaiceae?a, aiane?aeie o?ain-?ici?uaiiy
a?ae?ieneeueieo a?oi oeeo i??aiiceae?a. Oaeei /eiii io?eiai? niieoee
7-9.
A) Neioac oa aoaeiaa (2′-aoeaoieneaoiene)iaoeeueieo iioiaeieo
6-acaopaoeeeo oa 6-acaoeeoiceio
sse iaoiae iaea?aeaiiy aoeeeei/ieo aiaeiaia ioeeaiceaeia c a?aeuaieaiei
o?aaiaioii C2′-C3′ ie aeeipenoaee ?aaeoe?th opeiaoeeneeieueieo iioiaeieo
6-acao?aoeeeo c aeeiethth/eie ?aaaaioaie, a no?oeoo?? yeeo i?noeoueny
iio??aiee o?aaiaio -I-NH2-NH2-I-NH2-. Aea/aeanue ?aaeoe?y a aeaio
aa??aioao – c 2-iena-1,4-aooaiaeiieae?aoeaoaoii a ipenooiinoi eeneioe
Eueth?na, aai ae (2-aoeaoieneaoiene)iaoeea?ii?aeii. Neioac aeaieo
?aaaaio?a ipaaenoaaeaiee ia ?en. 7.
?en. 7
Iopeiaii aeeiethth/? ?aaaaioe aeicaieeee aeaiia niiniaaie caeienieoe
neioac aoeeeei/ieo aiaeiaia ioeeaiceaeia ia iniiai 6-acai??ei?aeeio, a
yeeo aoaeaaiaeia /anoeia iiaeaeth? opaaiaio peaioopaiiciiai oeeeeo (?en.
8 oa 9).
?en. 8.
N1-(2-Aoeaoieneaoiene)iaoee-6-acaopaoeee 10 aoei iaeapaeaii c aenieei
aeoiaeii (80%) c a?n-opeiaoeeneeie-6-acaopaoeeeo, aeei?enoiaoth/e
(2-aoeaoieneaoiene)iaoeeapiiiae (I) ye aee?ethth/ee ?aaaaio. I?e
ia?iaoe? 10 iaoaiieueiei ?ic/eiii ai?aeo a?aeaoaaeinue a?aeuaieaiiy
aoeaoeeueii? a?oie c ooai?aiiyi niieoee 11. Ioeeaiceaeiee aiaeia 10
oiiioaaee ii iieiaeaiith C4 6-acai??ei?aeeiiaiai oeeeeo ca aeiiiiiaith
iaioanoeueo?aeo oinoi?o a aaniethoiiio aeiienaii c ooai?aiiyi N1-(2-
aoeaoieneaoiene)iaoee-4-oii-6-acaopaoeeeo (12) (?en. 8).
A naith /a?ao, aiiioaaiiy 12 ipeaaei aei caiiuaiiy oiiooieoei? ia
aiiiia?oio c iaeii/aniei aiaeuaieaiiyi I-aoeaoeeueii? caoenii? apoie
aoeeeei/iiai opaaiaioo. Aoaeiaa iopeiaiiai iio?aeiiai 6-acaoeeoiceio –
N1-(2-aiaepieneaoiene)iaoee-4-aiiii-6-acao?aoeeeo (13) – aoea
anoaiiaeaia ca aeiiiiiaith niaeopineiii? ssI? oa OO. I?ioii N3-H ia
i?iyaey?oueny a II?-niaeo??, iaeiae iayai?noue aeaio neiaeaoieo neaiaeia
ipe 8 i.ae. (ca ?aooiie ??ciiai aeacae?aioaaiiy), oapaeoapieo aeey
ipioiiia aiiiiapoie 6-acaoeeoiceiia, oa aiaenooiinoue cnoao iaeneioio
iiaeeiaiiy a eoaeiiio napaaeiaeui a OO-niaeop? aiaipeoue ipi
N1-iieiaeaiiy caiinieea a 6-acai??ei?aeeiiaiio oeeee?.
?en. 9
Ianooiiei e?ieii aoei aea/aiiy ?aaeoe?e iopeiaiiy aoeeeei/ieo aiaeiaia
ioeeaiceaeia 6-acaiipeiiaeeiiaiai pyaeo ca aeiiiiiaith iaoiaeo
“neeieueii? eiiaeainaoei?” c aeeipenoaiiyi ae?aoeaoaoo
1,4-aeiiene-2-ienaaooaio (II) (?en. 9). Aeaiee ?aaaaio i?noeoue o?aaiaio
-INI2IAn, ui iiaea aeoeaoaaoenue eeneioaie Eueth?na (a aeaiiio aeiaaeeo
oao?aoei?eaeii ieiaa) iiae?aii aei 1-aoeaoieneiio?aeieo aoaeaaiae?a.
Aoei canoiniaaii noaiaeapoio iaoiaeeeo aeieiceethaaiiy a oiiaao
nipiuaiiai aapiaioo “nee?eueii? eiiaeainaoe??”, aeoiaey/e c
6-acaopaoeeeo. A ?acoeueoao? ?aaeoe?? iopeiaee noiio ipiaeoeoia c
nooo?aith iapaaaaith e?eueeino? iaeiiai c ieo. Aoea aeaeieaia pa/iaeia,
yea aiaepiciyeanue ca oiceei-oiii/ieie oapaeoapenoeeaie aiae niieoee 10,
iopeiaii? iaoiaeii i?yiiai aee?ethaaiiy nee?eueiaaiiai 6-acao?aoeeeo
aee?ea?ii?aeii (I). Ca aeaieie II?-niaeopo (i?enooi?noue neiaeaoo
i?ioiia N1-H) i ii iayaiinoi cnoao iaeneioio iiaeeiaiiy a eoaeieo oiiaao
a OO-niaeopi iopeiaiie niieooei aoea ipeienaia aoaeiaa
N3-(2-aoeaoieneaoiene)iaoee-6-acaopaoeeeo 15. Oaeei /eiii, a oiiaao
i?iaaaeaiiy eiiaeainaoe? iniiaiei i?iaeoeoii ?aaeoe?? nee?eueiaaiiai
acao?aoeeeo c ae?aoeaoaoiei ?aaaaioii (II) aeyaeany N3-?ciia?
ioeeaiceaeiiai aiaeiaa. Ie iia’yco?ii oea c iniaeeai aenieith
aeoeai?noth iaaoaeaaiaeiiai aee?ethth/iai ?aaaaioa i?ney eiai aeoeaaoe??
oao?aoei?eaeii ieiaa, ui i?aeoaa?aeaeo?oueny a?aeiinii aenieith
oaeaee?noth ?aaeoe?? ae?eiceethaaiiy (a 3-4 ?ace oaeaeoa, i?ae aeey
?eaioo?aiice).
Aeey iiaeoaapaeaeaiiy oeeo aeaieo ie ipiaaee “neeieueii eiiaeainaoei?” c
aeei?enoaiiyi ?aaaaioa (I) ia oieueee c 6-acaopaoeeeii 14, aea i c
4-oii-6-acaopaoeeeii 1a, a oaeiae c 6-acaoeeoiceiii. O anio aeiaaeeao
iapaaaaeii ooaipthaaany N3-iciiap (15,16). Ioaea, ni?iuaiee aa??aio
“nee?eueii? eiiaeainaoe??” ia aea? iiaeeeaino? io?eiaoe
N1-aoeeeeiioeeaiceaee aeaii? aoaeiae.
Oeyoii aca?iiae?? N3-(2-aoeaoieneaoiene)iaoee-4-oii-6-acaopaoeeeo (16) c
nie?oiaei ?ic/eiii ai?aeo aoei iopeiaii
N3-(2-aoeaoieneaoiene)iaoee-6-acaoeeoicei 17. Iayaiinoue a niaeo?? II?
oe??? niieoee neiaeaoo N1-ipioiio, neiaeaoo iaeiiai i?ioiio ?i?ii-a?oie
acaoeeoiceio oa i?ioii?a aoeaoeeo iaeiicia/ii aeaco? ia iieiaeaiiy
inaaaeiaeieiceaeiiai ca’yceo oa iayai?noue aoeaoeeueiiai caeeoeo.
5-Cai?uai? 6-acao?aoeeee oa ?o o?iiio?aei?
5-Cai?uai? 6-acai??ei?aeeie, a ia?oo /a?ao 5-ai?iieeneioi? iio?aei?, oa
?o o?iaiaeiae aeei?enoiaoaaeenue a aeai?e ?iaio? ye aaoa?ioeeee?/i?
eiiiiiaioe a neioac? ioeeaiceae?a. A ?iaio? cai?iiiiiaaii iia? i?aeoiaee
aei iaea?aeaiiy oaeeo iio?aeieo, aea/aii iai?aaeai?noue a?aeiia?aeieo
?aaeoe?e aaaaeaiiy cai?niee?a.
5-Apii-6-acao?aoeee 18 aoa aeoiaeiith niieoeith a neioacao
5-ea?aieneaee?eaiiiiiioiaeieo 19 a-d (?en. 10).
?en. 10
Anoape ea?aieneaee?eaiiiiiioiaeieo 6-acaopaoeeeo 20 iopeioaaee
aca?iiaei?th aiaeiiaiaeieo eeneio c aaniethoieie niepoaie a ipenooiinoi
oeipenoiai oiiiieo. I?e oeueiio aeoiaee anoapia iaaeeaeaeenue aei
eieueeinieo.
C iaoith aeoeaoaaiiy N4-iieiaeaiiy aaoa?ioeeeeo iaie aea/aeinue
o?iioaaiiy io?eiaieo acai??ei?aeeiiaeo iio?aeieo (?en. 11). Neioac
oiiiioiaeieo 5-cai?uaieo-ea?aieneaee?eaiiii-6-acao?aoeeeo 21 caeienieee
aei?th iaioanoeueoiaeo oinoipo ia aiaeiiaiaeii acai??ei?aeeie. I?e
oeueiio c’ynoaaeinue, ui ipenooiinoue N5-ea?aieneaee?eaiiiicaiinieeia
ianoieueee ciiith? aeaeopiiio ipepiaeo paaeoeieieo oeaiopia
aaoapioeeeeo, ui aaea?oueny iopeiaoe ipiaeoeoe caiiuaiiy aoiio eenith ia
aoii nipee oieueee ii N2-eapaiiieueiie apoii, ia ca/iiath/e ipe oeueiio
eapaiiieueio apoio a iieiaeaiii N4-acai??ei?aeeiiaiai eieueoey.
?en. 11
Anoaiiaeaii, ui 6-acaopaoeee 14 oa eiai 5-S-ea?aieneaee?eaiaeiae 22
oiiiothoueny a iapoo /apao ii iieiaeaiith N4 aaoa?ioeeeea, i oea ?
iai/iei iiaeoaapaeaeaiiyi aeaeopiiii? ipepiaee iaipaaeaiinoi oiiioaaiiy,
a ia noape/ieo aoaeoia aepaioaaiiy oeueiai iieiaeaiiy.
Oiiioaaiiy 5-cai?uaieo acai??ei?aeei?a caeienithaaee i?e eei’yo?ii?
aeoiaeieo paaaaioia a aeiienaii ipioyaii 2-3 aiae. Niieoee 22 c aenieei
aeoiaeii (iiiaae 80%) iapaoaipthaaeenue ia oiiiioiaeii 23.
I?enooi?noue aeaeo?iiiaeiii?iiai N5-cai?nieea a o?eaceiiaiio e?eueoe?
aaaea aei cieaeaiiy ?aaeoe?eii? caeaoiino? iieiaeaiiy N4 ii a?aeiioaiith
aei ioeeaio?eueieo ?aaaaio?a, ui aeicaiey? i?iaanoe naeaeoeaia cai?uaiiy
ea?aii?eueiiai aoiia eenith a iieiaeaii? N2 ia n??eo.
Aaaaeaiiy aoiio n??ee a iieiaeaiiy N2 nooo?ai aieeaa? ia iieiaeaiiy
neaiae?a i?ioii?a N1-H oa N3-H, ye? aeey 2-o?iiio?aeieo cnoioo? a neaaoa
iiea ? niinoa??aathoueny i?e 12-14 i.ae.
Aiieiai/ia aeoeaiinoue 6-acaoeeoeaeeio oa eiai aiaeiaia
Aeine?aeaeaiiy a?ieia?/ii? aeoeaiino? io?eiaieo i?aia?ao?a i?iaiaeeeinue
a ?inoeooo? i?e?ia?ieia?? oa a??onieia?? ?i. Ae.E.Caaieioiiai IAI
Oe?a?ie. Iiia?aaei?ie aeine?aeaeaiiyie aoei iieacaii, ui 6-acaoeeoeaeei,
aiiiaeueiee ioeeaiceae, no?oeoo?iee aiaeia oeeoeaeeio, neioaciaaiee a
?inoeooo? iieaeoey?ii? a?ieia?? ? aaiaoeee IAI Oe?a?ie, ?ia?ao?
?ai?iaeoeoe?th aaeaiia??ono oeio 1 a eoeueoo?? ee?oei Hela.
Aioeaaeaiia??onia ae?y 6-acaoeeoeaeeio aeyaeaia ? i?e aeine?aeaeaii?
aieeao eiai ia ?ai?iaeoeoe?th aaeaiia??ono oeio 2 a eoeueoo?? ee?oei
Hep-2 i?e aeei?enoaii? o?aaeeoe?eii? noaie, oiaoi i?e ia?iaoe? ee?oei
i?ney ca?aaeaiiy (Oaaeeoey 1).
Oaaeeoey 1
Aieea 6-acaoeeoeaeeio ia ?ai?iaeoeoe?th aaeaiia??ono
ethaeeie oeio 2 a eoeueoo?? ee?oei Hep-2
Eiioeaio?aoe?y, iea/ie ?ia?aoaaiiy ?ai?iaeoeoe?? a??ono, % Oeo? a??ono,
?8OOeAe50
125 100 0
62 100 0
16 82 2.7
8 86 ia aeine?aeaeoaaee
0.5 62 2.7
0
4.45
Aeine?aeaeaiiy i?ioea??onii? ae?? N1- oa N3-?ciia??a aoeeee?/ieo
aiaeia?a 6-acaoeeoiceio e?eueeio oei?a iieacaei, ui aiie iaeaea ia
i?eai?/othoue ?ai?iaeoeoe?th aaeaiia??ono a eoeueoo?? ee?oei. Na?aae
neioaciaaieo naei-ioeeaiceae?a 2′,3′-naei-6-acaoeeoeaeei i?iyaeya
i?ioea??onio aeoeai?noue eeoa a iaeneiaeuei?e iaoiene/i?e aeey ee?oei
eiioeaio?aoe?? 125 iea/ie. A?eueo aoaeoeaiei aoa
2′,3′-naei-5-iaoee-6-acaoeeoeaeei, yeee i?eai?/oaaa ?ai?iaeoeoe?th
aaeaiia??ono a iaioeo eiioeaio?aoe?yo, oa ana ae ia iano?eueee aeoeaii,
ye 6-acaoeeoeaeei (Oaaeeoey 2).
Oaaeeoey 2
Aieea 2′,3′-naei-5-iaoee-6-acaoeeoeaeeio ia ?ai?iaeoeoe?th
aaeaiia??ono a eoeueoo?? ee?oei
Eiioeaio?aoe?y,
iea/ie E?euee?noue ?io?eiaaieo ee?oei, % Aaeueioaaiiy ?ai?iaeoeoe??
a??ono, %
62 32 51
31 30 54
0 (eiio?ieue) 65
Oaeei /eiii, no?oeoo?ia o?ainoi?iaoe?y ae?eiceaeiiai caeeoeo a
iaea?aeaieo naei-iio?aeieo acaoeeoeaeeio nooo?ai iicia/a?oueny ia ?o
aioeaaeaiia??oni?e aeoeaiino? ii??aiyiii c 6-acaoeeoeaeeiii.
Aoea aea/aia a?ieia?/ia aeoeai?noue 5-ea?aieneaee?eaiiii- oa
o?iiioiaeieo 6-acaopaoeeeo a nenoai? in vitro ii a?aeiioaiith
aioa?ia??ono naeiae 386/79 oa ei?iiaa??ono naeiae I-115. Ciaeaeaii, ui
niieoee, ye? a?aeiinyoueny aei eeano o?iiio?aeieo, aeyaeythoue neaaeee,
aea aeia?a a?aeoai?thaaiee ?ia?aoth/ee aoaeo ii a?aeiioaiith aei iaio
a??on?a. Ai?iiiio?aei? 6-acao?aoeeeo oa?aeoa?ecothoueny iacia/iith
ae??th ia ei?iiaa??on, a oie /an ye aeo?aei? niieoee (6-acao?aoeee oa
2-o?i-6-acao?aoeee) a iiaeai?e na??? aeine?ae?a i?yeiai aieeao ia
ei?iiaa??on ia i?iyaeythoue.
AENIIAEE
1. Aecia/aii no?aoaa?th neioaco oa ?ic?iaeaii aoaeoeai? iaoiaee
iaea?aeaiiy iiaeo oeiia N1-aeieiceaeia 5-ea?aieneaiiiiaee?eiioiaeieo
6-acaopaoeeeo oa ?o 2-oiiaiaeiaia. Aecia/aii aieea eaoaeicaoipa,
oiii/ii? ipepiaee aoaeaaiaea oa aaoapioeeeei/ii? iniiae ia ooaipaiiy
N-aeieiceaeiiai ca’yceo ioeeaiceaeia a oiiaao ?aaeoe?? “nee?eueii?
eiiaeainaoe??”. Aia?oa aeey iaea?aeaiiy ioeeaiceaeieo iio?aeieo
6-acai??ei?aeeio aeei?enoaii iaeiinoaae?eiee aa??aio neioaco, ui
ia’?aeio? i?ioeane nee?ethaaiiy aaoa?ioeeeea oa eiai ae?eiceethaaiiy.
2. ?ic?iaeaii c?o/iee i?aia?aoeaiee iaoiae io?eiaiiy aenieiaeoeaiiai
i?ioea??oniiai i?aia?aoo – 6-acaoeeoeaeeio – a oiiaao ni?iuaiiai
iaeiinoaae?eiiai aa??aioo “nee?eueii? eiiaeainaoe??”. Iaoiae caoeuaii
iaoaioii Oe?a?ie.
3. Aeine?aeaeaii ia?eiaeaoia ieeneaiiy 6-acao?eaeeio, 6-acaoeeoeaeeio oa
?o iio?aeieo, a oaeiae i??aiiceae?a 6-acai??ei?aeei?a, iaea?aeaii ?yae
aoeeee?/ieo aiaeia?a ioeeaiceae?a ?c ?icuaieaiei ca’yceii C2′-C3′ /e c
a?aeuaieaiei o?aaiaioii C3′.
4. Aea/aii iaoiae neioaco aoeeee?/ieo aiaeia?a 6-acaoeeoeaeeio
aee?ethaaiiyi nee?eueiaaieo aaoa?ioeeee?/ieo iniia
2-(aoeaoieneaoiene)iaoeea?ii?aeii c ooai?aiiyi o?eueee N1-?ciia??a.
Io?eiaii niieoee, ui ? aiaeiaaie ?eaiioeeaiceae?a c a?aeuaieaiei
o?aaiaioii C2′-C3′.
5. Iieacaii, ui i?e aca?iiae?? 6-acao?aoeeeo oa 6-acaoeeoiceio c
2-iena-1,4-aooaiae?ieae?aoeaoaoii a oiiaao nipiuaiiai aapiaioo iaoiaeo
“neeieueii? eiiaeainaoei?” ooaipththoueny iapaaaaeii N3-iciiape
iiia?aaei?o aoeeee?/ieo aiaeia?a ioeeaiceae?a. Oaeei /eiii,
iaaaeaeaaoi?noue iai?yieo aee?ethaaiiy aoii?a acioo acai??ei?aeeio
iia’ycaia c aeoeai?noth aee?ethth/iai aaaioo.
6. Anoaiiaeaii, ui ipe oiiioaaiii 5-ea?aieneaee?eaiiiiiioiaeieo
6-acaopaoeeeo a?aeaoaa?oueny caiiuaiiy oieueee ii aoiio N-2, oiae? eiee
6-acaopaoeee oa eiai 5-ea?aieneaee?eiapeaioiiioiaeii a iapoo /apao
oiiiothoueny ii iieiaeaiith N-4, ui iia’ycaii c ia?a?iciiae?eii
aeaeo?iiiiai ca?yaeo aoiio.
7. Io?eiaii oa ioa?aeoa?eciaaii aeecueei 70 iiaeo niieoe – iio?aeieo
6-acai??ei?aeeiiaeo iniia ? ioeeaiceae?a oa ?o aoeeee?/ieo aiaeia?a.
I?iaaaeaii a?ieia?/i? aeine?aeaeaiiy ?yaeo iaea?aeaieo ?a/iaei.
Nienie iioae?eiaaieo i?aoeue ca oaiith aeena?oaoe??
Iaiyiee N.N., Oa?iaaneee N.N., Eiaueeineay A.E., Aeaenaaaa E.A., Oaeaiae
A.N. Aeeeiceee?iaaiea 5-N-aieiieeneioiuo i?iecaiaeiuo 6-acao?aoeeea e
2-oei-6-acao?aoeeea // Oe?. Oei. AEo?i. – 1988. O. 54, -N10. –
N.1094-1098.
Iaiyiee N.N., Oa?iaaneee N.N., Neei?a E.E., Aeaenaaaa E.A. Neioac e
niaeo?ineiie/aneea enneaaeiaaiey 3-oei-6-aeeeeaieiicaiauaiiuo
1,2,4-o?eaceiiiia-5 // Oe?. Oei. AEo?i. – 1988. O. 54, -N11. -N.
1197-1199.
Aeaenaaaa E.A., Iaeue/eeianeay E.E., Oaeaiae A.N., Iaiyiee N.N., Ii?aa?o
I.A., Iao?ooa I.A. Neioac e aeieiae/aneay aeoeaiinoue N1-caiauaiiuo
6-acaoeeoiceiia // Oei. Oa?i. AEo?i. – 1994. – N4. – N. 16-18.
Iaiyiee N.N., Oaeaiae A.N., Aeaenaaaa E.A., Eunaiei I.A. Neioac
iaaeeeiceaeiuo aiaeiaia 6-acaoeeoeaeeia e 6-acao?eaeeia // Oe?. Oei.
AEo?i. – 1995. O. 61, -N5. – N. 52-55.
Oaeaiae A.N., Iaiyiee N.N., Aeaena?aa ?.A., Aii/a?aiei A.N. Niin?a
iaea?aeaiiy 6-acaoeeoeaeeio. Iaoaio Oe?a?ie N 1785, – 1993.
?aoioueei E.I., Iaiyiee N.N., Oa?iaaneee N.N. Aeeyiea ?acee/iuo a?oii
i?iecaiaeiuo 6-acao?aoeeea ia eiaeae?iaaiea iaeioi?uo ae?onia.
//?anioaeeeaineay oeiea-naieia? “Oece/aneea, oeie/aneea e iaoaiaoe/aneea
iaoiaeu a nia?aiaiiie aeieiaee” – Eeoei?a, 1987.-N.108-109.
Oaeaiae A.N., Aeaenaaaa E.A., Iaiyiee N.N., Eiaueeineay A.E., Aeaoaaneay
O.A., Iina/ E.I., AEiaiiaaoay A.E., Aooaiei N.E. Neioac e
i?ioeaiae?oniay aeoeaiinoue caiauaiiuo 6-acao?eaeeiia // VIII
Ananithciue neiiiceoi “Eiiiiiaiou ioeeaeiiauo eeneio” – ?eaa, 1989. –
N. 35.
Aeaenaaaa E.A., Iaiyiee N.N., Oaeaiae A.N., Eiaueeineay A.E., Oa?iaaneee
N.N., Neei?a E.E., Eunaiei I.A., Aeaoaaneay O.A., Aeaaeeay A.A. Neioac
ioeeaiceaeia a ?yaeo ie?eieaeeia, 6-acaie?eieaeeia e 4-caiauaiiuo
aaico?eaciea. // IX Niaaonei-eiaeeeneee neiiiceoi ii oeiee i?e?iaeiuo
niaaeeiaiee – ?eaa, 1989. – N. 9-10.
Iaiyiee N.N., Aii/a?aiei A.N. Neioac ?eaioo?aiiceaeia 6-acao?aoeeea e
aai oeii?iecaiaeiuo. // III eiioa?aioeey iieiaeuo o/aiuo ?IE. – ?eaa,
1989. – N. 68.
Oaeaiae A.N., Iaiyiee N.N., Eenaiei I.A. Neioac ? aea/aiiy aoeeee?/ieo
aiaeia?a 6-acaoeeoeaeeio // XVII Eiioa?aioe?y c i?aai?/ii? o?i?? –
Oa?e?a, 1995. – N. 301.
Ognyanik S.S. Synthesis of glycoside and pseudoglycoside derivatives of
6-azauracil and 6-azacytosine.- Manuscript.
Thesis for candidate of sciences degree by speciality 02.00.10 –
bioorganic chemistry.
Institute of Bioorganic Chemistry and Petrochemistry, National Academy
of Sciences of Ukraine, Kyiv, 1999.
Thesis is devoted to the development of methods of synthesis and study
of properties of N-glycoside and pseudoglycoside derivatives of
6-azapyrimidines.
Efficient methods for the preparation of N1-glycosides of
5-carboxyalkylamino derivatives of 6-azauracil and their 2-thioanalogues
are described. Thio derivatives demonstrate week but well reproducible
inhibitory effect on pig enterovirus 386/79 and pig coronavirus P-115.
Method of the preparative synthesis of 6-azacytidine based on simplified
one-step variant of “silyl condensation” is proposed.
Acyclic analogues of 6-azapyrimidine nucleosides containing cleaved
C2′-C3′ bond or lacking C3′ fragment have been prepared by periodate
oxidation of corresponding nucleosides. It has been shown that obtained
compounds only slightly inhibit adenovirus reproduction in Hep-2 cell
culture.
Upon interaction of 6-azapyrimidines with 2-oxa-1,4-butandiol diacetate
under “silyl condensation” conditions mainly N3 – isomers have been
obtained by the alkylation of silylated heterocyclic bases with
2-(acetoxyethoxy)methyl bromide.
5-Amino acid derivatives of 6-azauracil and their 2-thioanalogues have
been prepared. It has been found that during thionation of
5-carboxyalkylamino derivatives of 6-azauracil only substitution at C-2
atom is observed, whereas 6-azauracil itself and its
5-carboxyalkylmercapto derivatives react mainly at C-4 position.
Key words: 6-azapyrimidines, nucleosides, acyclic analogues, “silyl
condensation”.
Iaiyiee N.N. Neioac ae?eiceaeieo oa inaaaeiae?eiceaeieo iio?aeieo
6-acao?aoeeeo oa 6-acaoeeoiceio.- ?oeiien.
Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.10 – a?ii?aai?/ia o?i?y.
?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie, Ee?a, 1999.
Aeena?oaoe?y i?enay/aia ?ic?iaoe? iaoiae?a neioaco oa aea/aiith
aeanoeainoae N-ae?eiceaeieo oa inaaaeiae?eiceaeieo iio?aeieo
6-acai??ei?aeei?a. ?ic?iaeaii iaoiaee io?eiaiiy ioeeaiceae?a
6-acao?aoeeeo oa 6-acaoeeoiceio oa ?o aoeeee?/ieo aiaeia?a ia iniia?
iaeiinoaae?eiiai aa??aioo “nee?eueii? eiiaeainaoe??” oa ia?eiaeaoiiai
ieeneaiiy ioeeaiceae?a. Aea/aii a?ieia?/io aeoeai?noue iaea?aeaieo
niieoe.
Eeth/ia? neiaa: 6-acai??ei?aeeie, ioeeaiceaee, aoeeee?/i? aiaeiae,
“nee?eueia eiiaeainaoe?y”.
Iaiyiee N.N. Neioac aeeeiceaeiuo e inaaaeiaeeeiceaeiuo i?iecaiaeiuo
6-acao?aoeeea e 6-acaoeeoiceia. – ?oeiienue.
Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oeie/aneeo iaoe
ii niaoeeaeueiinoe 02.00.10 – aeii?aaie/aneay oeiey.
Einoeooo aeii?aaie/aneie oeiee e iaooaoeiee IAI Oe?aeiu, Eeaa, 1999.
Aeenna?oaoeey iinayuaia ?ac?aaioea iaoiaeia neioaca e eco/aieth naienoa
N-aeeeiceaeiuo e inaaaeiaeeeiceaeiuo i?iecaiaeiuo 6-acaie?eieaeeiia.
?ac?aaioaiu iaoiaeu iieo/aiey ioeeaiceaeia 6-acao?aoeeea e
6-acaoeeoiceia e eo aoeeeee/aneeo aiaeiaia ia iniiaa iaeiinoaaeeeiiai
aa?eaioa “neeeeueiie eiiaeainaoeee” e ia?eiaeaoiiai ieeneaiey
ioeeaiceaeia. Eco/aia aeieiae/aneay aeoeaiinoue iieo/aiiuo niaaeeiaiee.
Eeth/aaua neiaa: 6-acaie?eieaeeiu, ioeeaiceaeu, aoeeeee/aneea aiaeiae,
“neeeeueiay eiiaeainaoeey”
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