SYNTHESIS OF NOVEL 5-ARYL/HETARYLIDENYL 3-(2-METHYL-5,6,7,8-TETRAHYDROBENZO[4,5]THIENO[2,3-d]PYRIMIDIN-4-YL)-2-THIOXOTHIAZOLIDIN-4-ONES

被引：4

作者：

Mendoza, Kimberly ^{[1
]}

Kamila, Sukanta ^{[1
]}

Biehl, Edward R. ^{[1
]}

机构：

[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA

来源：

HETEROCYCLES | 2014年 / 88卷 / 01期

关键词：

Rhodanine; Knoevenagel Condensation; Microwave Heating; 5,6,7,8-Tetrahydrobenzothiophene; Pyrimidine-4-amine; MICROWAVE-ASSISTED SYNTHESIS; RHODANINE DERIVATIVES; ONE-POT; INHIBITORS; ANTAGONIST;

D O I：

10.3987/COM-13-S(S)36

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a variety of novel 5-substituted titled compounds containing a priviledged rhodanine scaffold is described. The synthesis involves a microwave (MW) assisted Knoevenagel condensation of 3-(2-methyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one with suitably substituted aromatic aldehydes. However, these condensations fail with aliphatic aldehydes. The 2-thioxothiazolidin-4-one (rhodanine) precursor was prepared by the condensation of 2-thioxothiazolidin-4-one-di-(carboxymethyl)trithiocarbonyl and 4,5,6,7-tetrahydrobenzo[4,5]thienyl[2,3-d]2-methylpyrimidin-4-amine in the presence of K2CO3.

引用

页码：741 / 753

页数：13

共 36 条

[1]

Abdel- Rahman B.A., 2007, Acta Pharm, V57, P395, DOI [10.2478/v10007-007-0032-6, DOI 10.2478/V10007-007-0032-6]

[2]

Alvord E, 1934, U.S. Patent, Patent No. 1962109

[3] SOME 3-SUBSTITUTED RHODANINES [J].

BROWN, FC ;

BRADSHER, CK ;

MORGAN, EC ;

TETENBAUM, M ;

WILDER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :384-388

[4] Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones [J].

Bruno, G ;

Costantino, L ;

Curinga, C ;

Maccari, R ;

Monforte, F ;

Nicolò, F ;

Ottanà, R ;

Vigorita, MG .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :1077-1084

[5]

CIBA A. G., 1946, Swiss Patent, Patent No. 242300

[6] NOVEL BENZOTHIOPHENECARBOXAMIDOTETRAZOLE, BENZOFURANCARBOXAMIDOTETRAZOLE, AND NAPHTHALENECARBOXAMIDOTETRAZOLE AS POTENTIAL ANTIALLERGY AGENTS [J].

CONNOR, DT ;

CETENKO, WA ;

MULLICAN, MD ;

SORENSON, RJ ;

UNANGST, PC ;

WEIKERT, RJ ;

ADOLPHSON, RL ;

KENNEDY, JA ;

THUESON, DO ;

WRIGHT, CD ;

CONROY, MC .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (05) :958-965

[7] Rhodanine derivatives as inhibitors of JS']JSP-1 [J].

Cutshall, NS ;

O'Day, C ;

Prezhdo, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (14) :3374-3379

[8] Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides [J].

Erben, Friedrich ;

Kleeblatt, Dennis ;

Sonneck, Marcel ;

Hein, Martin ;

Feist, Holger ;

Fahrenwaldt, Thomas ;

Fischer, Christine ;

Matin, Abdul ;

Iqbal, Jamshed ;

Ploetz, Michael ;

Eberle, Juergen ;

Langer, Peter .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (24) :3963-3978

[9]

Faftah A., 2006, J CHIN CHEM SOC-TAIP, V53, P402

[10] MECHANISM OF INHIBITION OF HISTIDINE DECARBOXYLASE BY RHODANINES [J].

FREE, CA ;

MAJCHROWICZ, E ;

HESS, SM .

BIOCHEMICAL PHARMACOLOGY, 1971, 20 (07) :1421-+

← 1 2 3 4 →