Strategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides:: selective inhibitors of PKCβ

被引：22

作者：

Faul, MM ^{[1
]}

Grutsch, JL ^{[1
]}

Kobierski, ME ^{[1
]}

Kopach, ME ^{[1
]}

Krumrich, CA ^{[1
]}

Staszak, MA ^{[1
]}

Udodong, U ^{[1
]}

Vicenzi, JT ^{[1
]}

Sullivan, KA ^{[1
]}

机构：

[1] Eli Lilly & Co, Lilly Corp Ctr, Global Chem Proc Res & Dev, Indianapolis, IN 46285 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 36期

关键词：

N-(azacycloalkyl)bisindolylmaleimides; angiogenesis; vascular endothelial growth factor;

D O I：

10.1016/S0040-4020(03)00973-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-(Azacycloalkyl)bisindolylmaleimides 1 have been identified to be selective inhibitors of PKCbeta. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for preparation of N-(azacycloalkyl) indole 5, indole-3-acetamide 8 and indole-3-glyoxylate ester 4 derivatives. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：7215 / 7229

页数：15

共 24 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].

ABDELMAGID, AF ;

MARYANOFF, CA ;

CARSON, KG .

TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598

[3]

ADACHI M, 1985, CHEM PHARM BULL, V33, P1826

[4] Efficient synthesis of the 5-HT2c receptor agonist, Org 37684 [J].

Adams, DR ;

Duncton, MAJ .

SYNTHETIC COMMUNICATIONS, 2001, 31 (13) :2029-2036

[5] 2-(2-Aminophenyl)-acetaldehyde dimethyl acetal: A novel reagent for the protection of carboxylic acids. [J].

Arai, E ;

Tokuyama, H ;

Linsell, MS ;

Fukuyama, T .

TETRAHEDRON LETTERS, 1998, 39 (1-2) :71-74

[6] REACTION OF SOME INDOLES AND INDOLINES WITH 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE [J].

BERGMAN, J ;

CARLSSON, R ;

MISZTAL, S .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (09) :853-862

[7]

CARPINO PA, 1996, Patent No. 9638471

[8] Convenient preparation of N-substituted indoles by modified Leimgruber-Batcho indole synthesis [J].

Coe, JW ;

Vetelino, MG ;

Bradlee, MJ .

TETRAHEDRON LETTERS, 1996, 37 (34) :6045-6048

[9]

Danis RP, 1998, INVEST OPHTH VIS SCI, V39, P171

[10] IN-SITU NMR SPECTROSCOPIC STUDIES OF ANILINE ORTHO ACYLATION (SUGASAWA REACTION) - THE NATURE OF REACTION INTERMEDIATES AND LEWIS-ACID INFLUENCE ON YIELD [J].

DOUGLAS, AW ;

ABRAMSON, NL ;

HOUPIS, IN ;

KARADY, S ;

MOLINA, A ;

XAVIER, LC ;

YASUDA, N .

TETRAHEDRON LETTERS, 1994, 35 (37) :6807-6810

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