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Pereslavtseva A.V.,RAS Institute of Technical Chemistry | Tolmacheva I.A.,RAS Institute of Technical Chemistry | Slepukhin P.A.,Russian Academy of Sciences | El'Tsov O.S.,Ural Federal University | And 3 more authors.
Chemistry of Natural Compounds | Year: 2014

A-seco-triterpenoids with a methylketone group were synthesized from epimeric 3-hydroxy-3-methyl-1-cyano-2,3-seco-triterpenoids of the lupane and 19β,28-epoxy-18αH-oleanane types, which were formed by a Grignard reaction. The resulting methylketones underwent under base-catalysis conditions an intramolecular cyclization to form A-pentacyclic β-substituted alkenenitriles. The synthesized compounds included 3-methyl-1-cyano-19β,28- epoxy-2,3-seco-2-nor-18αH-olean-3-one and methyl 3-methyl-1-cyano-2- norlup-1(3),20(29)-dien-28-oate, which inhibited in vitro reproduction of human immunodeficiency virus type 1. © 2014 Springer Science+Business Media New York. Source


Tolmacheva I.A.,RAS Institute of Technical Chemistry | Igosheva E.V.,RAS Institute of Technical Chemistry | Savinova O.V.,RSPC of Epidemiology and Microbiology | Boreko E.I.,RSPC of Epidemiology and Microbiology | Grishko V.V.,RAS Institute of Technical Chemistry
Chemistry of Natural Compounds | Year: 2014

Amide conjugates with four structural types of β-amino alcohols were synthesized from 2,3-seco-18αH-oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids. Esters were prepared by reaction of C-3-hydroxy derivatives of A-seco-triterpenoids with dicarboxylic acid anhydrides. The antiviral activity of the synthesized compounds was studied against herpes simplex virus type I. The most active amide was 5a (5.7 μM, MTC/EC 50 32.2). © 2014 Springer Science+Business Media New York. Source


Tolmacheva I.A.,RAS Institute of Technical Chemistry | Igosheva E.V.,RAS Institute of Technical Chemistry | Vikharev Yu.B.,RAS Institute of Technical Chemistry | Grishko V.V.,RAS Institute of Technical Chemistry | And 3 more authors.
Russian Journal of Bioorganic Chemistry | Year: 2013

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 (EC50 8.7 and 4.1 μM). The ethyl β-alaninate diamide was shown to combine antiherpetic and anti-HIV activity (EC50 5.1 μM). For the active compounds, the ratios of maximum tolerable concentrations to EC50 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. © 2013 Pleiades Publishing, Ltd. Source

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