Synthesis of β-hydroxypropanoic acid derivatives as potential anti-inflammatory, analgesic and antimicrobial agents

被引：28

作者：

Abdel-Rahman, Hamdy M. ^{[1
]}

Hussein, Mostafa A.

机构：

[1] Assiut Univ, Fac Pharm, Pharmaceut Med Chem Dept, Assiut 71526, Egypt

[2] Assiut Univ, Fac Pharm, Pharmaceut Organ Chem Dept, Assiut 71526, Egypt

来源：

ARCHIV DER PHARMAZIE | 2006年 / 339卷 / 07期

关键词：

beta-hydroxypropanoic acid derivatives; anti-inflammatory; antimicrobial; 1,2,4-triazoles; 1,3,4-oxadiazoles;

D O I：

10.1002/ardp.200600016

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new 3-(substituted) 3-hydroxy-propanoic acid ethyl esters 1a-c, hydrazides 2a-c, thiosemicarbazides 3a-f, and semicarbazides 3g, 3h has been synthesized. Cyclization of compounds 3a-d in basic medium yielded 1,2,4-triazole-5-thiones 4a-d. On the other hand, reaction of hydrazides 2a-c with CS2 in basic medium afforded 1,3,4-oxadiazole-5-thiones 5a-c. All the synthesized compounds were characterized by their physical and spectral analyses data. The newly synthesized compounds were evaluated for their anti-inflammatory, analgesic, and antimicrobial activities. Compounds 1c, 3g, 4a, 4b, 4c, and 3c exhibited comparable anti-inflammatory activity to that of indomethacin and compounds 1c, 4c, and 5c were more analgesics than acetyl salicylic acid. Compounds 4b, 4c, and 3c showed superior GI safety profile (33.3%, 33.3% and 50.0% ulceration) than that of indomethacin (100% ulceration) at 100 mg/kg oral dose. Compounds 4b, 4c, and 5c were also non-toxic with a median lethal dose (LD50) up to 200 mg/kg. The antibacterial and antifungal screenings identified compounds 3c, 4b, 4d, 5a, and 5b as the most effective against a variety of tested microorganisms.

引用

页码：378 / 387

页数：10

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