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(R)- И (S)-ИЗОМЕРЫ 3-МЕТИЛСПЕРМИДИНА
专利权人:
FEDERALNOE GOSUDARSTVENNOE BJUDZHETNOE UCHREZHDENIE NAUKI INSTITUT MOLEKULJARNOJ BIOLOGII IM. V.A.EHNGELGARDTA ROSSIJSKOJ AKADEMII NAUK (IMB RAN)
发明人:
KHOMUTOV MAKSIM ALEKSEEVICH,Хомутов Максим Алексеевич,KHIVONEN MERVI,Хивонен Мерви,KEJNANEN TUOMO,Кейнанен Туомо,VEPSALAJNEN JOUKO,Вепсалайнен Йоуко,ALKHONEN LEENA,Алхонен Леена,KHOMUTOV ALEKSEJ RADIE
申请号:
RU2012153080/04
公开号:
RU0002558952C2
申请日:
2012.12.10
申请国别(地区):
RU
年份:
2015
代理人:
摘要:
FIELD: chemistry.SUBSTANCE: invention relates to novel trihydrochlorides of (R)- and (S)-isomers of 1,8-diamino-3-methyl-4-azaoctane (3-methylspermidine), corresponding to structural formulae given below and to a method for production thereof. Said compounds can be used in vitro and in vivo to investigate individual cell functions of easily interconvertible and partially interchangeable spermine and spermidine, which are vital for tumour cells and pathogenic trypanosomatids. The (R)-isomer of 3-methylspermidine trihydrochloride is the first metabolically stable functionally active spermidine mimetic.. A method of producing said isomers includes alkylating salts of (R)- and (S)-isomers of N1-protected 1,3-diaminobutane sulphamide with N-protected 1-amino-4-butylhalides, followed by successive removal of protective groups and treatment of the obtained residue with hydrochloric acid solution. The alkylating agent used can be N-(phthaloyl)-1-amino-4-butylhalides in aprotic polar solvents or N-(4-iodobutyl)phthalimide in dimethyl formamide in the presence of calcium carbonate. Removal of the phthalyl protection is normally carried out with hydrazine hydrate in alcohol. Removal of benzyloxycarbonyl groups is normally carried out by catalytic hydrogenation over Pd-black at atmospheric pressure in a mixture of methanol and acetic acid.EFFECT: converting the obtained triacetates of R)- and (S)-isomers of 1,8-diamino-3-methyl-4-azaoctane into tetrahydrochlorides is carried out with aqueous hydrochloric acid solution.7 cl, 5 dwg, 5 exИзобретение относится к новым тригидрохлоридам (R)- и (S)-изомеров 1,8-диамино-3-метил-4-азаоктана (3-метилспермидина), соответствующих нижеуказанным структурным формулам, и к способу их получения. Указанные соединения могут быть использованы in vitro и in vivo для изучения индивидуальных клеточных функций легковзаимопревращающихся и частично взаимозаменяемых спермина и спермидина, которые жизненно необходимы опухолевым клеткам и болезнетворным тр
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