Convenient synthesis and antimicrobial evaluation of some novel 2-substituted-3-methylbenzofuran derivatives

被引:80
作者
Abdel-Aziz, Hatem A. [1 ]
Mekawey, Amal A. I. [2 ]
Dawood, Kamal M. [3 ]
机构
[1] Natl Res Ctr, Dept Appl Organ Chem, Cairo 12622, Egypt
[2] Al Azhar Univ, Reg Ctr Mycol & Biotechnol, Cairo, Egypt
[3] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
关键词
Benzofurans; Pyrazoles; 3,1-Benzoxazine; Antimicrobial activity; X-ray single crystal; ANTIFUNGAL ACTIVITIES; ANTITUMOR AGENTS; BENZOFURAN; 1,3,4-OXA(THIA)DIAZOLE; ANTICONVULSANT; ANTIBACTERIAL; ANTAGONISTS; PYRIDINE;
D O I
10.1016/j.ejmech.2009.02.020
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The reaction of 3-methylbenzofuran-2-carbohydrazide (1) with 1-phenyl-2-bromoethanone (2a) or 2-chloro-1-(4-chlorophenyl)ethanone (2b) afforded (Z)-1,2-di[(3-methylbenzofuran-2-carbohydrazido]-1-arylethenes Sa and 5b, respectively. Single crystal X-ray analyses of compound 5a proved that the reaction proceeds in 2:1 molar ratio and ruled out the other possible structures 1,3,4-oxadiazine derivative 6 or E-isomer 7. Furthermore, both of 3-(3-methylbenzofuran-2-yl)-3-oxopropanenitrile (9) and 3-methyl-2-benzofuranoyl chloride (15) were used as starting materials for the synthesis of several compounds, such as pyrazoles 10 and 14, oxime 11, hydrazones 12a, b and 3,1-bezoxazine 19. The newly synthesized compounds were tested for their antimicrobial activity against five fungal species and four bacterial species also their minimum inhibitory concentration (MIC) against most of test organisms was performed. Some of these compounds exhibited a significant antimicrobial activity. (C) 2009 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:3637 / 3644
页数:8
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