Microwave-assisted synthesis of the antihyperglycemic drug rosiglitazone

被引：42

作者：

Gaonkar, Santosh L. ^{[1
]}

Shimizu, Hiroki ^{[1
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Hokkaido Ctr, Res Inst Genome Based Biofactory, Express & Mol Regulat Res Grp, Sapporo, Hokkaido 0628517, Japan

来源：

TETRAHEDRON | 2010年 / 66卷 / 18期

基金：

日本学术振兴会;

关键词：

Thiazolidine-2,4-dione; Rosiglitazone; Antihyperglycemic agent; Microwave-assisted Synthesis; ORGANIC-SYNTHESIS; DERIVATIVES; DISEASE; HYPERTENSION; SERIES;

D O I：

10.1016/j.tet.2010.03.006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed a simple, rapid, high yielding, and environmentally benign microwave assisted total synthesis of rosiglitazone, an antihyperglycemic agent for diabetes mellitus Type II. We used microwave heating successfully to improve reactions in four of six steps and obtain quicker and higher yields. In addition, all intermediates were isolated in good yields with crystallizations only and did not require chromatographic separations. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3314 / 3317

页数：4

共 24 条

[1] THE SYNTHESIS OF BRL-49653 - A NOVEL AND POTENT ANTIHYPERGLYCEMIC AGENT [J].

CANTELLO, BCC ;

CAWTHORNE, MA ;

HAIGH, D ;

HINDLEY, RM ;

SMITH, SA ;

THURLBY, PL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (10) :1181-1184

[2] [[OMEGA-(HETEROCYCLYLAMINO)ALKOXY]BENZYL]-2,4-THIAZOLIDINEDIONES AS POTENT ANTIHYPERGLYCEMIC AGENTS [J].

CANTELLO, BCC ;

CAWTHORNE, MA ;

COTTAM, GP ;

DUFF, PT ;

HAIGH, D ;

KINDLEY, RM ;

LISTER, CA ;

SMITH, SA ;

THURLBY, PL .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (23) :3977-3985

[3] Rosiglitazone Attenuates the Severity of Sodium Taurocholate-induced Acute Pancreatitis and Pancreatitis-associated Lung Injury [J].

Chen, Chen ;

Xu, Sheng ;

Wang, Wei-Xing ;

Ding, You-Ming ;

Yu, Kai-Huan ;

Wang, Bin ;

Chen, Xiao-Yan .

ARCHIVES OF MEDICAL RESEARCH, 2009, 40 (02) :79-88

[4]

Cruz P, 1996, TETRAHEDRON LETT, V37, P1113

[5] Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].

de la Hoz, A ;

Díaz-Ortiz, A ;

Moreno, A .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178

[6]

DORIS D, 2007, CHEM REV, V107, P2563

[7] Synthesis of novel 3-[5-ethyl-2-(2-phenoxy-ethyl)pyridin]-5-substituted isoxazoline libraries via 1,3-dipolar cycloaddition and evaluation of antimicrobial activities [J].

Gaonkar, S. L. ;

Rai, K. M. Lokanatha ;

Prabhuswamy, B. .

MEDICINAL CHEMISTRY RESEARCH, 2007, 15 (7-8) :407-417

[8] Microwave-assisted synthesis and evaluation of anti-inflammatory activity of new series of N-substituted 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde derivatives [J].

Gaonkar, S. L. ;

Rai, K. M. Lokanatha ;

Shetty, N. Suchetha .

MEDICINAL CHEMISTRY RESEARCH, 2009, 18 (03) :221-230

[9] A new method for the generation of azoalkenes from ketohydrazones and its application to the synthesis of tetrahydropyridazine derivatives [J].

Gaonkar, SL ;

Rai, KML .

TETRAHEDRON LETTERS, 2005, 46 (35) :5969-5970

[10] Growth inhibition and induction of apoptosis in MCF-7 breast cancer cells by a new series of substituted-1,3,4-oxadiazole derivatives [J].

Kumar, Akhilesh ;

D'Souza, Saritha S. ;

Gaonkar, S. L. ;

Rai, K. M. L. ;

Salimath, Bharathi P. .

INVESTIGATIONAL NEW DRUGS, 2008, 26 (05) :425-435

← 1 2 3 →