Solution-Phase Parallel Synthesis of a Multi-substituted Benzo[b]thiophene Library

被引：49

作者：

Cho, Chul-Hee ^{[1
]}

Neuenswander, Benjamin ^{[2
]}

Lushington, Gerald H. ^{[2
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Univ Kansas, NIH, Ctr Excellence Chem Methodol & Lib Dev, Lawrence, KS 66047 USA

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2009年 / 11卷 / 05期

基金：

美国国家卫生研究院;

关键词：

ESTROGEN-RECEPTOR MODULATORS; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; TUBULIN POLYMERIZATION; ELECTROPHILIC CYCLIZATION; COMBINATORIAL CHEMISTRY; DEVELOPMENT SETTINGS; ESTIMATE SOLUBILITY; DRUG DISCOVERY; DERIVATIVES;

D O I：

10.1021/cc9000604

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Generation of a library using parallel syntheses of multi-substituted benzo[b]thiophenes is described. The requisite 3-iodobenzo[b]thiophenes are readily prepared in excellent yields from various alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I-2 in CH2Cl2. The heteroaromatic carbon-iodine bonds allow further diversification by palladium-catalyzed Suzuki-Miyaura, Sonogashira, Heck, and carboalkoxylation chemistry to give multi-substituted benzo[b]thiophene derivatives.

引用

收藏

页码：900 / 906

页数：7

相关论文

共 60 条

[31] Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation [J].

Liu, H ;

Liu, J ;

van Breemen, RB ;

Thatcher, GRJ ;

Bolton, JL .

CHEMICAL RESEARCH IN TOXICOLOGY, 2005, 18 (02) :162-173

[32]

Magarian R.A., 1994, CURR MED CHEM, V1, P61

[33] Conformationally restricted macrocyclic analogues of combretastatins [J].

Mateo, Carmen ;

Alvarez, Raquel ;

Perez-Melero, Concepcion ;

Pelaez, Rafael ;

Medarde, Manuel .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (22) :6316-6320

[34]

Merritt AT, 1998, COMB CHEM HIGH T SCR, V1, P57

[35] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].

MIYAURA, N ;

SUZUKI, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483

[36] Reactivity and synthetic utility of 1-(arenesulfonyloxy)benziodoxolones [J].

Muraki, T ;

Togo, H ;

Yokoyama, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (08) :2883-2889

[37] Chirality transfer in gold-catalyzed carbothiolation of o-alkynylphenyl 1-arylethyl sulfides [J].

Nakamura, Itaru ;

Sato, Takuma ;

Terada, Masahiro ;

Yamamoto, Yoshinori .

ORGANIC LETTERS, 2008, 10 (13) :2649-2651

[38] Gold-catalyzed intramolecular carbothiolation of alkynes:: Synthesis of 2,3-disubstituted benzothiophenes from (α-alkoxy alkyl) (ortho-alkynyl phenyl) sulfides [J].

Nakamura, Itaru ;

Sato, Takuma ;

Yamamoto, Yoshinori .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (27) :4473-4475

[39] Structure activity relationship for a family of benzothiophene selective estrogen receptor modulators including raloxifene and arzoxifene [J].

Overk, Cassia R. ;

Peng, Kuan-Wei ;

Asghodom, Rezene T. ;

Kastrati, Irida ;

Lantvit, Daniel D. ;

Qin, Zhihui ;

Frasor, Jonna ;

Bolton, Judy L. ;

Thatcher, Gregory R. J. .

CHEMMEDCHEM, 2007, 2 (10) :1520-1526

[40] Discovery and synthesis of [6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-hydroxyphenyl)]benzo[b]thiophene: A novel, highly potent, selective estrogen receptor modulator [J].

Palkowitz, AD ;

Glasebrook, AL ;

Thrasher, KJ ;

Hauser, KL ;

Short, LL ;

Phillips, DL ;

Muehl, BS ;

Sato, M ;

Shetler, PK ;

Cullinan, GJ ;

Pell, TR ;

Bryant, HU .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (10) :1407-1416

← 1 2 3 4 5 6 →