Synthesis of the antitumoural agent batracylin and related isoindolo[1,2-b]quinazolin-12(10H)-ones

被引：40

作者：

Martinez-Viturro, Carlos A.

Dominguez, Domingo ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Fac Quim, Dept Quim Organ, Santiago De Compostela 15782, Spain

[2] Univ Santiago de Compostela, Fac Quim, Unidad Asociada, CSIC, Santiago De Compostela 15782, Spain

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 06期

关键词：

batracylin; quinazolines; Mitsunobu reaction; quinazolinones;

D O I：

10.1016/j.tetlet.2006.11.168

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of batracylin and related isoindolo[1,2-b]quinazolin-12-ones from easily accessible o-acylanilines is reported. The preparation of these tetracyclic compounds through a Mitsunobu reaction followed by spontaneous cyclodehydration shows the ability of this methodology to afford good yields of a wide variety of diversely 7, 8, 9, 10-substituted isoindoloquinazolinones in two steps. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1023 / 1026

页数：4

共 15 条

[1]

ADGER BM, 1975, J CHEM SOC PERK T 1, P45, DOI 10.1039/p19750000045

[2] Pyrrolidinohydroquinazolines -: a novel class of CCR3 modulators [J].

Anderskewitz, R ;

Bauer, R ;

Bodenbach, G ;

Gester, D ;

Gramlich, B ;

Morschhäuser, G ;

Birke, FW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (03) :669-673

[3] Novel inhibitors of acetyl- and butyrylcholinesterase derived from the alkaloids dehydroevodiamine and rutaecarpine [J].

Decker, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (03) :305-313

[4] Synthesis and cytotoxic activity of conjugates of muramyl and normuramyl dipeptides with batracylin derivatives [J].

Dzierzbicka, K ;

Trzonkowski, P ;

Sewerynek, P ;

Mysliwski, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) :978-986

[5]

Eguchi S., 1994, HETEROCYCL COMMUN, V1, P51

[6] THE SYNTHESIS OF SUBSTITUTED 2-AMINOPHENYL HETEROCYCLIC KETONES [J].

FRYER, RI ;

ZHANG, PW ;

RIOS, R .

SYNTHETIC COMMUNICATIONS, 1993, 23 (07) :985-992

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

Guillaumel, J ;

Léonce, S ;

Pierré, A ;

Renard, P ;

Pfeiffer, B ;

Arimondo, PB ;

Monneret, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (03) :379-386

[8] A novel class of sodium/calcium exchanger inhibitor:: design, synthesis, and structure-activity relationships of 3,4-dihydro-2(1H)-quinazolinone derivatives [J].

Hasegawa, H ;

Muraoka, M ;

Ohmori, M ;

Matsui, K ;

Kojima, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (11) :3721-3735

[9]

KABBE HJ, 1978, LIEBIGS ANN CHEM, P398

[10] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF ISOINDOLO[1,2-B]QUINAZOLINONE AND ISOINDOLO[2,1-A]BENZIMIDAZOLE DERIVATIVES RELATED TO THE ANTITUMOR AGENT BATRACYLIN [J].

MEEGALLA, SK ;

STEVENS, GJ ;

MCQUEEN, CA ;

CHEN, AY ;

YU, C ;

LIU, LF ;

BARROWS, LR ;

LAVOIE, EJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) :3434-3439

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