NDLI: Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids

Content Provider	Springer Nature Link
Author	Tolmacheva, I. A. Igosheva, E. V. Vikharev, Yu. B. Grishko, V. V. Saviva, O. V. Boreko, E. I. Eremin, V. F.
Copyright Year	2013
Abstract	Amides of four types were synthesized derived from 2,3-seco-18αH-oleanane and 2,3-secolupane mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3-C3′ and C28-C28′ biscondensed amides with two A-secotriterpene backbones obtained by the interaction of monocarboxylic A-seco acids with lysine. Among the synthesized monoand diamide derivatives, potential inhibitors of herpes simplex virus type 1 replication were found, namely, some compounds with an ethyl β-alaninate fragment (EC$_{50}$ 8.7 and 4.1 μM). The ethyl β-alaninate diamide was shown to combine antiherpetic and anti-HIV activity (EC$_{50}$ 5.1 μM). For the active compounds, the ratios of maximum tolerable concentrations to EC$_{50}$ ranged from 9.7 to 40.8. The synthesized amides did not show any marked cytotoxic effects against human rabdomiosarcoma RD TE32, A549 lung carcinoma, and melanoma MS cell lines.
Starting Page	186
Ending Page	193
Page Count	8
File Format	PDF
ISSN	10681620
Journal	Russian Journal of Bioorganic Chemistry
Volume Number	39
Issue Number	2
e-ISSN	1608330X
Language	English
Publisher	SP MAIK Nauka/Interperiodica
Publisher Date	2013-03-22
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	allobetulone amides antiviral activity A-secotriterpenoids betulin betulonic acid cytotoxic activity herpes simplex virus HIV-1 triterpenoid bisderivatives Biochemistry Bioorganic Chemistry Organic Chemistry Biomedicine general
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry

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