3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]

被引：35

作者：

Akaev, Andrey A. ^{[1
]}

Villemson, Elena V. ^{[1
]}

Vorobyeva, Nataliya S. ^{[2
]}

Majouga, Alexander G. ^{[1
,2
]}

Budynina, Ekaterina M. ^{[1
]}

Melnikov, Mikhail Ya ^{[1
]}

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1-3, Moscow 119991, Russia

[2] Natl Univ Sci & Technol MISiS, Leninskiy Pr 4, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 11期

关键词：

MDM2; INHIBITORS; CYCLOPROPANES; SPIROTRYPROSTATIN; CONSTRUCTION; FACILE;

D O I：

10.1021/acs.joc.7b00529

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthetic approach to biologically relevant spiro[pyrrolidine-3,3'-oxindoles] was developed on the basis of the cascade transformation of 3-(2-azidoethyl)-oxindoles via Staudinger/aza-Wittig/Mannich reactions. The parent azides were readily synthesized through a nudeophilic ring opening of spiro[cyclopropane-1,3'-oxindoles] with the azide ion. A series of new spiro[pyrrolidine-3,3'-oxindoles] with various (het)aryl substituents at the C2 and C5 positions of the pyrrolidine ring were synthesized. In vitro experiments revealed their high crotoxicity toward LNCaP and PC-3 tumor cell lines.

引用

页码：5689 / 5701

页数：13

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