Studies on Semisynthesis and Antibacterial Activity of 3-Heterocyclicthiomethyl Cephalosporins

Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (10): 1564.

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Studies on Semisynthesis and Antibacterial Activity of 3-Heterocyclicthiomethyl Cephalosporins

HAO Lan¹, HUI Xin-Ping¹, ZHANG Zi-Yi¹, GUAN Zuo-Wu², HE Yu-Lin³, YU Hong-Juan³

1. National Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;
2. Institute of Applied Pharmacy, Beijing Medical University, Beijing 100083, China;
3. Department of Microbiology, Lanzhou Medical College, Lanzhou 730000, China

Received:1999-01-28 Online:1999-10-24 Published:1999-10-24

Abstract

Abstract: Fourteen new mother nucleus of 7-amino-3-heterocyclicthiomethyl cephalosporins 2a_2n were synthesized by the reaction of 7-ACA with 2-substituted 1,3,4-oxadiazol-5-thione-1a_1g, 2-arylamino-1,3,4-thiadiazol-5-thione 1h_1l or 1, 2, 4-triazoline-5-hione 1m, 1n. Two new compounds, 7-(1-aryl-5-methyl-1H-1,2,3-triazol-4-formylamido)-3-(2-substituted-1,3,4-oxadiazol-5-thiomethyl) cephalosporins 4c, 4d, were obtained by the acylation of 7-amino group of 2c, 2d with 1-aryl-5-methyl-1H-1,2,3-triazol-4-formyl chloride 3a, 3b. The structures of the compounds synthesized were confirmed by elementary analyses, IR, ¹HNMR and FAB-MS. In preliminary antibacterial sensitivity test, the compounds 2a_2l were found to show higher antibacterial activity than 7-ACA against Gram-positive bacteria, 4c, 4d were found to have significant antibacterial activity against both Gram-positive and Gram-negative bacteria.

Key words: Cephalosporin, Heterocycle, Semisynthesis, Antibacterial activities

CLC Number:

R914

TrendMD:

HAO Lan, HUI Xin-Ping, ZHANG Zi-Yi, GUAN Zuo-Wu, HE Yu-Lin, YU Hong-Juan . Studies on Semisynthesis and Antibacterial Activity of 3-Heterocyclicthiomethyl Cephalosporins[J]. Chem. J. Chinese Universities, 1999, 20(10): 1564.

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Studies on Semisynthesis and Antibacterial Activity of 3-Heterocyclicthiomethyl Cephalosporins

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