SYNTHESIS AND EVALUATION FOR BIOLOGICAL ACTIVITIES OF 2-THIO-ACYLATED THIAZOLES CONTAINING PYRAZOLE MOIETY

被引：3

作者：

Masumoto, Eiichi ^{[1
]}

Kashige, Nobuhiro ^{[1
]}

Nagabuchi, Hayate ^{[1
]}

Okabe-Nakahara, Fumi ^{[1
]}

Maruoka, Hiroshi ^{[1
]}

机构：

[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, 8-19-1 Nanakuma, Fukuoka 8140180, Japan

来源：

HETEROCYCLES | 2019年 / 98卷 / 12期

关键词：

Pyrazole; Thiazole; Rhodanine; Acylation; DNA Cleavage; ANTIFUNGAL ACTIVITY; DNA; DERIVATIVES; POTENT; PYRAZOL-3-ONES; ANTIBACTERIAL; REACTIVITY; DISCOVERY; BINDING;

D O I：

10.3987/COM-19-14181

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An approach to the synthesis of novel 2-thio-acylated thiazoles containing pyrazole moiety is described. The pyrazole-thiazolethione derivative as the key building block for bis-heterocycles was formed via a Knoevenagel-type condensation of rhodanine with pyrazol-3-one. Thermal treatment of the pyrazole-thiazolethione derivative with acid anhydride and/or chloride in refluxing toluene caused diacylation reaction to give the corresponding 2-thio-acylated thiazoles containing pyrazole moiety. All the synthesized compounds were characterized by spectroscopic analysis and were tested for their DNA cleavage activity in vitro. Furthermore, they were evaluated for their antifungal activity against Candida albicans and Saccharomyces cerevisiae.

引用

页码：1736 / 1746

页数：11

共 36 条

[1] Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring
Bharti, S. K.
Nath, G.
Tilak, R.
Singh, S. K.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) : 651 - 660
[2] Synthesis and structure activity relationships of novel small molecule cathepsin D inhibitors
Dumas, J
Brittelli, D
Chen, JS
Dixon, B
Hatoum-Mokdad, H
König, G
Sibley, R
Witowsky, J
Wong, S
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (17) : 2531 - 2536
[3] FRIEDMAN AE, 1991, NUCLEIC ACIDS RES, V19, P2595
[4] From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles
Fustero, Santos
Sanchez-Rosello, Maria
Barrio, Pablo
Simon-Fuentes, Antonio
[J]. CHEMICAL REVIEWS, 2011, 111 (11) : 6984 - 7034
[5] Synthesis, hypoglycemic activity and molecular modeling studies of pyrazole-3-carbohydrazides designed by a CoMFA model
Hernandez-Vazquez, Eduardo
Aguayo-Ortiz, Rodrigo
Jose Ramirez-Espinosa, Juan
Estrada-Soto, Samuel
Hernandez-Luis, Francisco
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 : 10 - 21
[6] Microwave-assisted, one-pot syntheses and fungicidal activity of polyfluorinated 2-benzylthiobenzothiazoles
Huang, Wei
Yang, Guang-Fu
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (24) : 8280 - 8285
[7] Kai J., 2002, BIOORG MED CHEM LETT, V12, P3275
[8] Synthesis, analgesic, anti-inflammatory and antimicrobial studies of 2,4-dichloro-5-fluorophenyl containing thiazolotriazoles
Karthikeyan, Mari Sithambaram
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) : 827 - 833
[9] KASHIGE N, 1995, BIOL PHARM BULL, V18, P653
[10] SYNTHESIS OF PYRAZOLE DERIVATIVES POSSESSING ANTICANCER ACTIVITY: CURRENT STATUS
Kumari, Simpal
Paliwal, Sarvesh
Chauhan, Rajani
[J]. SYNTHETIC COMMUNICATIONS, 2014, 44 (11) : 1521 - 1578

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