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Novel convenient synthesis of biologically active esters of hydroxylamineстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 11 декабря 2015 г.
- Авторы: Khomutov Maxim A., Mandal Swati, Weisell Janne, Saxena Neiha, Simonian Alina R., Vepsalainen Jouko, Madhubala Rentala, Kochetkov Sergey N.
- Журнал: Amino Acids
- Том: 38
- Номер: 2
- Год издания: 2009
- Издательство: Springer Verlag
- Местоположение издательства: Germany
- Первая страница: 509
- Последняя страница: 517
- DOI: 10.1007/s00726-009-0410-0
- Аннотация: Alkylation of ethyl N-hydroxyacetimidate with readily available methanesulfonates of functionally substituted alcohols and subsequent deprotection of aminooxy group is a novel and convenient method to prepare functionally substituted esters of hydroxylamine with high overall yield. This approach is a good alternative to well-known reaction of N-hydroxyphthalimide with alcohols under the Mitsunobu conditions. The properties of ethoxyethylidene protection of aminooxy group on the contrary to that of N-alkoxyphthalimide group allow to perform a wide spectra of the transformations in the radical of N-protected hydroxylamine derivatives. This is essential for synthetic strategies consisting in the introduction of N-protected aminooxy group at one of the first steps of synthesis and subsequent transformations of the radical. The inhibitory effect of one of the newly synthesized compound, 1-guanidinooxy-3-aminopropane (GAPA), was compared with that of well-known inhibitors of ornithine decarboxylase namely, alpha-difluoromethylornithine (DFMO) and 1-aminooxy-3-aminopropane (APA) on Leishmania donovani, a protozoan parasite that causes visceral leishmaniasis. GAPA, on the contrary with APA and DFMO, in micromolar concentrations, inhibited the growth of both amastigotes and promastigotes of sodium antimony gluconate-resistant forms of L. donovani.
- Добавил в систему: Кочетков Сергей Николаевич