Synthesis of formazans from Mannich base of 5-(4-chlorophenyl amino)-2-mercapto-1,3,4-thiadiazole as antimicrobial agents

Loại tài liệu:

Article

Tác giả:

Sah, P.

Đề mục:

Arabian Journal of Chemistry

Nhà xuất bản:

Elsevier Ltd.

Ngày xuất bản:

April 2014

Định dạng:

pdf

Nguồn gốc:

Arabian Journal of Chemistry, Volume 7, Issue 2, April 2014, Pages 181-187

Ngôn ngữ:

eng

Lượt xem:

Lượt tải:

Nội dung

5-(4-Chlorophenyl amino)-2-mercapto-1,3,4-thiadiazole (I) was refluxed with formaldehyde and ammonium chloride in ethanol yielding the Mannich base 5-(4-chloro phenyl amino)-3-aminomethyl-2-mercapto-1,3,4-thiadiazole (II). Esterification with 4-chloro-(2,6-dinitro phenoxy)-ethyl acetate (III) under anhydrous conditions gave the intermediate (IV). Subsequent hydrazinolysis with hydrazine hydrate gave the corresponding hydrazide 3-amino methyl-5-(4-chloro phenyl amino)-2-mercapto-4′-(2′,6′-dinitro phenoxy)-acetyl hydrazide (V). The hydrazide was converted into the Schiff bases (VI_a_–_b) by reacting with 2-chlorobenzaldehyde and 3-methoxy-4-hydroxy benzaldehyde in presence of methanol containing 2–3 drops of acetic acid. Diazotisation with aromatic amines, sulphanilic acid and sulphur drugs gave the formazans (VII_a_–_g) respectively. Chemical structures have been established by elemental analysis and the spectral techniques of FTIR, ¹H NMR and mass. Antimicrobial activity (in vitro) was evaluated against the two pathogenic bacterial strains. Escherichia coli and Salmonella typhi, three fungal strains Aspergillus niger, Penicillium species and Candida albicans. The compounds have shown moderate activity.

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Synthesis of formazans from Mannich base of 5-(4-chlorophenyl amino)-2-mercapto-1,3,4-thiadiazole as antimicrobial agents

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