One-pot synthesis and anticancer studies of 2-arylamino-5-aryl-1,3,4-thiadiazoles

被引：63

作者：

Kumar, Dalip ^{[1
]}

Vaddula, Buchi Reddy ^{[1
]}

Chang, Kuei-Hua ^{[2
,3
]}

Shah, Kavita ^{[2
,3
]}

机构：

[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India

[2] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

[3] Purdue Univ, Purdue Canc Ctr, W Lafayette, IN 47907 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 08期

关键词：

1,3,4-Thidiazoles; Anticancer agents; One-pot synthesis; Cancer cell lines; Oxidative cyclization; 1,3,4-THIADIAZOLE DERIVATIVES; ANTIPROLIFERATIVE ACTIVITY; ANTICONVULSANT ACTIVITY; EFFICIENT SYNTHESIS; 2-AMINO-1,3,4-THIADIAZOLE; AGENTS; INHIBITORS; COMPLEXES; CHLORIDE; LIQUID;

D O I：

10.1016/j.bmcl.2011.02.083

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 2-arylamino-5-aryl-1,3,4-thiadiazoles 1a-j were synthesized and screened for their anticancer activity against various human cancer cell lines. The novel one-pot synthesis of 1,3,4-thiadiazoles was achieved by refluxing aryl aldehydes, hydrazine hydrate, and aryl isothiocyanates in methanol followed by oxidative cyclization with ferric ammonium sulfate. The compounds 1g-j with trimethoxyphenyl at the C-5 position displayed extremely potent anticancer activity with at least twofold selectivity (IC(50): 4.3-9.2 mu M). The nature of substituent on the C-2 arylamino ring may be critical in opting for the selectivity towards a particular cancer cell. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2320 / 2323

页数：4

共 44 条

[1]

Barboiu M, 1996, Met Based Drugs, V3, P227, DOI 10.1155/MBD.1996.227

[2] Complexes of cobalt(II), nickel(II) and copper(II) with a thia ligand;: 2,5-bis(2-pyridyl)-1,3,4-thiadiazole:: structural identification [J].

Bentiss, F ;

Lagrenée, M ;

Wignacourt, JP ;

Holt, EM .

POLYHEDRON, 2002, 21 (04) :403-408

[3]

DAVIS M, 1979, ORG COMPD SULPHUR SE, V5, P440

[4] Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities [J].

Dogan, HN ;

Duran, A ;

Rollas, S ;

Sener, G ;

Uysal, MK ;

Gülen, D .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :2893-2898

[5]

ELSON PJ, 1988, INVEST NEW DRUG, V6, P97

[6]

Foroumadi A, 2007, DARU, V15, P89

[7] Synthesis and in vitro antibacterial evaluation of N-[5-(5-vitro-2-thienyl)-1, 3,4-thiadiazole-2-yl] piperazinyl quinolones [J].

Foroumadi, A ;

Mansouri, S ;

Kiani, Z ;

Rahmani, A .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (09) :851-854

[8] Electrospray ionization mass spectrometric study of 1,3,4-thiadiazole-copper complexes: comparison with 1,3,4-oxadiazole derivatives [J].

Franski, R .

JOURNAL OF MASS SPECTROMETRY, 2004, 39 (06) :705-706

[9] Study on 1,3,4-thiadiazole derivatives as novel multifunctional oil additives [J].

Gao, YJ ;

Zhang, ZJ ;

Xue, QJ .

MATERIALS RESEARCH BULLETIN, 1999, 34 (12-13) :1867-1874

[10] Synthesis of substituted 1,3,4-thiadiazoles using Lawesson's reagent [J].

Gierczyk, B ;

Zalas, M .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2005, 37 (03) :213-222

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