Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring

被引:92
作者
Iqbal, A. K. Mohammed [1 ]
Khan, Ashraf Y. [1 ]
Kalashetti, Mallikarjun B. [1 ]
Belavagi, Ningaraddi S. [1 ]
Gong, Young-Dae [2 ]
Khazi, Imitiyaz Ahmed M. [1 ]
机构
[1] Karnatak Univ, Dept Chem, Dharwad 580003, Karnataka, India
[2] Dongguk Univ, Ctr Innovat Drug Lib Res, Coll Sci, Seoul, South Korea
关键词
Thiazolidinediones; Pioglitazone analogs; Hypoglycemic activity; Hypolipidemic activity; PEROXISOME; ACTIVATION;
D O I
10.1016/j.ejmech.2012.04.015
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Novel thiazolidinedione derivatives were synthesized by incorporating pharmacologically significant heterocycles viz, substituted thiazole, triazole, and oxadiazole moieties linked to the central phenyl ring via heteroatomlinkage with one/two carbon spacer as the structural analogs of Pioglitazone by employing multistep synthetic protocols. Structures of all the newly synthesized intermediates and target molecules were established by analytical and spectral data. These newly synthesized compounds were screened for their invivo hypoglycemic and hypolipidemic activities in male wistar rats. Some of the synthesized compounds demonstrated good activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:308 / 315
页数:8
相关论文
共 28 条
[21]   Thiazolidinedione use, fluid retention, and congestive heart failure [J].
Nesto, RW ;
Bell, D ;
Bonow, RO ;
Fonseca, V ;
Grundy, SM ;
Horton, ES ;
Le Winter, M ;
Porte, D ;
Semenkovich, CF ;
Smith, S ;
Young, LH ;
Kahn, R .
DIABETES CARE, 2004, 27 (01) :256-263
[22]   Synthesis and primary cytotoxicity evaluation of new 5-benzylidene-2, 4-thiazolidinedione derivatives [J].
Patil, Vijay ;
Tilekar, Kalpana ;
Mehendale-Munj, Sonali ;
Mohan, Rhea ;
Ramaa, C. S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) :4539-4544
[23]   Thiazolidinediones and insulin resistance:: Peroxisome proliferator-activated receptor γ activation stimulates expression of the CAP gene [J].
Ribon, V ;
Johnson, JH ;
Camp, HS ;
Saltiel, AR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (25) :14751-14756
[24]   (Z)-5-ARYLMETHYLENEHYDANTOINS AND (E)-5-ARYLMETHYLENEHYDANTOINS - SPECTROSCOPIC PROPERTIES AND CONFIGURATION ASSIGNMENT [J].
TAN, SF ;
ANG, KP ;
FONG, YF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (12) :1941-1944
[25]   The PPARs: From orphan receptors to drug discovery [J].
Willson, TM ;
Brown, PJ ;
Sternbach, DD ;
Henke, BR .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (04) :527-550
[26]   The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones [J].
Willson, TM ;
Cobb, JE ;
Cowan, DJ ;
Wiethe, RW ;
Correa, ID ;
Prakash, SR ;
Beck, KD ;
Moore, LB ;
Kliewer, SA ;
Lehmann, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (03) :665-668
[27]   Drug therapy: Thiazolidinediones [J].
Yki-Jarvinen, H .
NEW ENGLAND JOURNAL OF MEDICINE, 2004, 351 (11) :1106-1118
[28]   THE CYCLIZATION OF 3-ACYLDITHIOCARBAZATE ESTERS [J].
YOUNG, RW ;
WOOD, KH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (02) :400-403