A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

被引：17

作者：

Carbone, Anna ^{[1
]}

Spano, Virginia ^{[1
]}

Parrino, Barbara ^{[1
]}

Ciancimino, Cristina ^{[1
]}

Attanasi, Orazio A. ^{[2
]}

Favi, Gianfranco ^{[2
]}

机构：

[1] Univ Palermo, Dipartimento Sci & Tecnol Biol Chim & Farmaceut, I-90123 Palermo, Italy

[2] Univ Urbino Carlo Bo, Dipartimento Sci Biomol, I-61029 Urbino, Italy

来源：

MOLECULES | 2013年 / 18卷 / 03期

关键词：

topsentin; bis-indole alkaloids; antitumor activity; ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)-carbonyl]-1H-pyrrole-3-carboxylates; ORGANIC-SYNTHESIS; METAL-IONS; CYTOTOXICITY EVALUATION; BIS(INDOLE) ALKALOIDS; ANTITUMOR PROPERTIES; NATURAL-PRODUCTS; INDOLE ALKALOIDS; SPONGOSORITES SP; SPONGE; NORTOPSENTIN;

D O I：

10.3390/molecules18032518

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of substituted ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl) carbonyl]-1H-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between beta-dicarbonyl compounds 12a-e and 1,2-diaza-1,3-diene (DD) 13. Derivatives 10a,c-e, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the in vitro one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound 9e, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.

引用

页码：2518 / 2527

页数：10

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