SYNTHESIS AND BETA-LACTAMASE INHIBITORY ACTIVITY OF 6-[(1-HETEROARYLTHIOETHYL-1,2,3-TRIAZOL-4-YL)-METHYLENE]PENAM SULFONES

被引：38

作者：

IM, C

MAITI, SN

MICETICH, RG

DANESHTALAB, M

ATCHISON, K

PHILLIPS, OA

KUNUGITA, C

机构：

[1] UNIV ALBERTA,FAC PHARM & PHARMACEUT SCI,EDMONTON T6G 2N8,AB,CANADA

[2] SYNPHAR LABS INC,EDMONTON T6E 5V2,AB,CANADA

[3] TAIHO PHARMACEUT CO LTD,TOKUSHIMA RES CTR,TOKUSHIMA,JAPAN

来源：

JOURNAL OF ANTIBIOTICS | 1994年 / 47卷 / 09期

关键词：

D O I：

10.7164/antibiotics.47.1030

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

The synthesis of beta-lactamase inhibitory activity of a series of sodium 6-[(1-heteroarylthioethyl-1,2,3-triazol-4-yl)methylene]penicillanate 1,1-dioxides are described. Their activity was compared with tazobactam and sulbactam. The Z-isomers were more active than the E-isomers. The in vitro activity of the Z-isomers of the phenylthiadiazole derivatives (13a and 15a) was better than sulbactam against the tested beta P-lactamases and comparable to tazobactam especially against TEM-2 and cephalosporinase. But their synergistic activity with five antibiotics was inferior to tazobactam.

引用

收藏

页码：1030 / 1040

页数：11

相关论文

共 15 条

[1] 6-(SUBSTITUTED METHYLENE)PENEMS, POTENT BROAD-SPECTRUM INHIBITORS OF BACTERIAL BETA-LACTAMASE .3. STRUCTURE-ACTIVITY-RELATIONSHIPS OF THE 5-MEMBERED HETEROCYCLIC-DERIVATIVES [J].

BENNETT, I ;

BROOM, NJP ;

BRUTON, G ;

CALVERT, S ;

CLARKE, BP ;

COLEMAN, K ;

EDMONDSON, R ;

EDWARDS, P ;

JONES, D ;

OSBORNE, NF ;

WALKER, G .

JOURNAL OF ANTIBIOTICS, 1991, 44 (03) :331-337

[2] 6-(SUBSTITUTED METHYLENE)PENEMS, POTENT BROAD-SPECTRUM INHIBITORS OF BACTERIAL BETA-LACTAMASE .5. CHIRAL 1,2,3-TRIAZOLYL DERIVATIVES [J].

BENNETT, IS ;

BROOKS, G ;

BROOM, NJP ;

CALVERT, SH ;

COLEMAN, K ;

FRANCOIS, I .

JOURNAL OF ANTIBIOTICS, 1991, 44 (09) :969-978

[3] THE ACID-CATALYZED REACTION OF ALKYL AZIDES UPON CARBONYL COMPOUNDS [J].

BOYER, JH ;

HAMER, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (04) :951-954

[4]

BROOM NJP, 1989, Patent No. 321187

[5] SYNTHESIS OF A POTENT BETA-LACTAMASE INHIBITOR-1,1-DIOXO-6-(2-PYRIDYL)METHYLENEPENICILLANIC ACID AND ITS REACTION WITH SODIUM METHOXIDE [J].

CHEN, YL ;

CHANG, CW ;

HEDBERG, K .

TETRAHEDRON LETTERS, 1986, 27 (30) :3449-3452

[6] STRUCTURE-ACTIVITY-RELATIONSHIPS OF 6-(HETEROCYCLYL)-METHYLENE PENAM SULFONES - A NEW CLASS OF BETA-LACTAMASE INHIBITORS [J].

CHEN, YPL ;

CHANG, CW ;

HEDBERG, K ;

GUARINO, K ;

WELCH, WM ;

KIESSLING, L ;

RETSEMA, JA ;

HASKELL, SL ;

ANDERSON, M ;

MANOUSOS, M ;

BARRETT, JF .

JOURNAL OF ANTIBIOTICS, 1987, 40 (06) :803-822

[7] CP-45,899, A BETA-LACTAMASE INHIBITOR THAT EXTENDS ANTIBACTERIAL SPECTRUM OF BETA-LACTAMS - INITIAL BACTERIOLOGICAL CHARACTERIZATION [J].

ENGLISH, AR ;

RETSEMA, JA ;

GIRARD, AE ;

LYNCH, JE ;

BARTH, WE .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1978, 14 (03) :414-419

[8]

MICETICH RG, 1986, SYNTHESIS-STUTTGART, P292

[9] SYNTHESIS AND BETA-LACTAMASE INHIBITORY PROPERTIES OF 2-BETA-[(1,2,3-TRIAZOL-1-YL)METHYL]-2-ALPHA-METHYLPENAM-3-ALPHA-CARBOXYLIC ACID 1,1-DIOXIDE AND RELATED TRIAZOLYL DERIVATIVES [J].

MICETICH, RG ;

MAITI, SN ;

SPEVAK, P ;

HALL, TW ;

YAMABE, S ;

ISHIDA, N ;

TANAKA, M ;

YAMAZAKI, T ;

NAKAI, A ;

OGAWA, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) :1469-1474

[10] 2,4,6-TRIPYRIDINIO-1,3,5-TRIAZINE TRICHLORIDE, A NEW AND MILD ESTERIFICATION AGENT FOR PREPARATION OF PENICILLIN ESTERS [J].

MURAKAMI, M ;

HAJIMA, M ;

TAKAMI, F ;

YOSHIOKA, M .

HETEROCYCLES, 1990, 31 (11) :2055-2064