Synthesis and biological activity of 6H-isoindolo [2,1-a]indol-6-ones, analogues of batracylin, and related compounds

被引：72
作者：
Guillaumel, J
Léonce, S
Pierré, A
Renard, P
Pfeiffer, B
Arimondo, PB
Monneret, C
机构：
[1] Inst Curie, UMR 176 CNRS, Serv Pharmacochim, F-75248 Paris 5, France
[2] Inst Rech Servier, F-92450 Suresnes, France
[3] ADIR, F-92415 Courbevoie, France
[4] USM0503, MNHN, UMR5153 CNRS, INSERM UR565, F-75231 Paris 5, France
来源：
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2006年 / 41卷 / 03期
关键词：
batracylin; isoindolo[2,1-a]indole; indole; amino-basic chain; intramolecular wittig reaction;
D O I：
10.1016/j.ejmech.2005.10.008
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.
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页码：379 / 386
页数：8
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