S 98 Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives [Electronic resource] / V. V. Grishko, I. A. Tolmacheva, N. V. Galaiko, A. V. Pereslavceva, L. V. Anikina, L. V. Volkova, B. A. Bachmetyev, P. A. Slepukhin // European Journal of Medicinal Chemisrty. - 2013. - Vol.68. - С. 203-211. - Bibliogr. : p. 211 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ANTIVIRAL ACTIVITY -- ACETYLHYDRAZONE -- BETULONIC ACID Аннотация: It has been previously shown that semi-synthetic A-secotriterpene acetylhydrazones of 1-cyano-28-methoxy-28-oxo-2,3-seco-2-norlup-20(29)-en-3-al and 1-cyano-2,3-seco-2-nor-19β,28-epoxy-18αH-olean-3-al (1, 2) inhibit the vesicular stomatitis virus (VSV) replication. To improve the antiviral activity against VSV, structural modifications of compounds 1 and 2 were performed, and new A-secoderivatives containing the acetylhydrazone fragment were obtained from betulonic acid and its methyl ester, allobetulone, and 3-oxo-18βH-glycyrrhetinic acid methyl ester. The inhibitory effects of these compounds on VSV replication in porcine embryo kidney (PEK) cells were determined after infection. It was shown that introduction of the 3′-acetyl-5′-methyl-1′,3′,4′-oxadiazoline fragment into lupane triterpene structures lead to an increase in the antiviral activity of A-secotriterpene derivatives. However, the presence of a heterocyclic moiety enhanced toxic activity and reduced the therapeutic indices of these agents. Investigation in the anti-proliferative activity of the heterocyclic derivatives has shown high sensitivity of A-549, MS and RD tumor cell lines to lupane (R)-oxadiazoline 11a. The pro-apoptotic effect of 11a was confirmed by the AnnexinV/PI analysis \\\\expert2\\NBO\\European Journal of Medicinal Chemistry\\2013, v.68, p.203.pdf |
S 98 Synthesis of ferrocenyl-substituted triterpenoids [Electronic resource] / V. A. Glushkov, L. V. Anikina, T. I. Gorbunova, A. N. Nedugov, P. A. Slepukhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1226-1230. - Bibliogr. : p. 1230 (26 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): FERROCENYL-SUBSTITUTED TRITERPENOIDS -- SYNTHESIS -- CROTONIC CONDENSATION Аннотация: Products of crotonic condensation of ferrocenecarbaldehyde with allobetulone and betolonic acid methyl ester are described \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1226-1230.pdf |
S 98 Synthesis of Triterpene A-Condensed Azoles [Electronic resource] / N. V. Galaiko, A. V. Nazarov, I. A. Tolmacheva, P. A. Slepukhin, Y. B. Vikharev, O. A. Maiorova, V. V. Grishko // Chemistry of Heterocyclic Compounds. - 2014. - Article in Press Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALFA-HYDROXIMINO KETONES -- 1,2,3-TRIAZOLES -- ALLOBETULONE Аннотация: Lupane and 18αH-oleanane α-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)-C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)-C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 μM) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines. |
S 98 Synthesis of A-Pentacyclic Triterpene α,β-Alkenenitriles [Electronic resource] / A. V. Pereslavceva, I. A. Tolmacheva, P. A. Slepukhin, O. S. Eltsov, I. I. Kucherov, V. F. Eremin, V. V. Grishko // Chemistry of Natural Compounds. - 2014. - Vol.49, №6. - С. 1059-1066. - Bibliogr. : p. 1066 (24 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALFA,BETA- ALKENENITRILES -- A-SECO-TRITERPENOIDS -- ALLOBETULONE Аннотация: 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. \\\\expert2\\nbo\\Chemistry of Natural Compounds\\2014, V.49, N6, p.1059.pdf |