Novel C-2 substituted carbapenem derivatives part IV. Synthesis and biological activity of five membered heteroaromatic derivatives

被引：7

作者：

Branch, CL ^{[1
]}

Burton, G ^{[1
]}

Clarke, GJ ^{[1
]}

Coulton, S ^{[1
]}

Douglas, JD ^{[1
]}

Eglington, AJ ^{[1
]}

Guest, AW ^{[1
]}

Hinks, JD ^{[1
]}

Hird, NW ^{[1
]}

Holland, RK ^{[1
]}

Hunt, E ^{[1
]}

Knott, SJ ^{[1
]}

Moss, SF ^{[1
]}

Naylor, A ^{[1
]}

Pearson, MJ ^{[1
]}

Takle, AK ^{[1
]}

机构：

[1] SmithKline Beecham Pharmaceut, Surrey RH3 7AJ, England

来源：

JOURNAL OF ANTIBIOTICS | 1998年 / 51卷 / 02期

关键词：

D O I：

10.7164/antibiotics.51.210

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, antibacterial activity, and stability to human dehydropeptidase-1 (DHP-1) of a novel series of (5R,6S)-6-[(1R)-1-hydroxyethyl]-2-heterocyclylcarbapen-2-em-3-carboxylates are described. Of the compounds investigated 1,5-disubstituted pyrazol-3-yl and 3-substituted isoxazol-5-yl derivatives have the best combination of antibacterial activity and stability to DHP-1. They are particularly active against community-acquired respiratory tract pathogens and have stabilities to DHP-1 superior to that of meropenem.

引用

页码：210 / 220

页数：11

共 16 条

[1] EMERGENCE OF DRUG-RESISTANT PNEUMOCOCCAL INFECTIONS IN THE UNITED-STATES [J].

BREIMAN, RF ;

BUTLER, JC ;

TENOVER, FC ;

ELLIOTT, JA ;

FACKLAM, RR .

JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, 1994, 271 (23) :1831-1835

[2] Novel C-2 substituted carbapenem derivatives .2. Synthesis and structure-activity relationships of isoxazolidin-2-yl, isoxazolidin-2-yl and 2-pyrazolin-2-yl carbapenems generated using 1,3-dipolar cycloaddition chemistry [J].

Burton, G ;

Clarke, GJ ;

Douglas, JD ;

Eglington, AJ ;

Frydrych, CH ;

Hinks, JD ;

Hird, NW ;

Hunt, E ;

Moss, SF ;

Naylor, A ;

Nicholson, NH ;

Pearson, MJ .

JOURNAL OF ANTIBIOTICS, 1996, 49 (12) :1266-1274

[3] Novel C-2 substituted carbapenem derivatives .1. Synthesis and biological activity of non-aromatic heterocyclic derivatives [J].

Burton, G ;

Clear, NJC ;

Eglington, AJ ;

Guest, AW ;

Hunt, E ;

Naylor, A ;

Pearson, MJ ;

Takle, AK .

JOURNAL OF ANTIBIOTICS, 1996, 49 (12) :1258-1265

[4] TOTAL SYNTHESIS OF THIENAMYCIN ANALOGS .3. SYNTHESES OF 2-ARYL AND 2-HETEROARYL ANALOGS OF THIENAMYCIN [J].

CAMA, LD ;

WILDONGER, KJ ;

GUTHIKONDA, R ;

RATCLIFFE, RW ;

CHRISTENSEN, BG .

TETRAHEDRON, 1983, 39 (15) :2531-2549

[5] Novel C-2 substituted carbapenem derivatives .3. Synthesis and biological activity of 2-(functionalised ethenyl, oxyimino methyl and alpha-[hydroxy]benzyl)-carbapenems [J].

Clear, NJC ;

Davies, JS ;

Eglington, AJ ;

Fell, SCM ;

Hinks, JD ;

Hird, NW ;

Hunt, E ;

Moss, SF ;

Pearson, MJ .

JOURNAL OF ANTIBIOTICS, 1997, 50 (03) :237-245

[6]

DONDONI A, 1986, SYNTHESIS-STUTTGART, P757

[7] NOVEL SYNTHESES OF THE CARBAPENEM KEY INTERMEDIATES, (3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE AND (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]-4-CARBOXYMETHYL-2-AZETIDINONE, FROM (S)-ETHYL LACTATE [J].

ITO, Y ;

KOBAYASHI, Y ;

KAWABATA, T ;

TAKASE, M ;

TERASHIMA, S .

TETRAHEDRON, 1989, 45 (18) :5767-5790

[8] PREVALENCE AND RESISTANCE MECHANISMS OF COMMON BACTERIAL RESPIRATORY PATHOGENS [J].

JACOBY, GA .

CLINICAL INFECTIOUS DISEASES, 1994, 18 (06) :951-957

[9] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].

NAHM, S ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818

[10]

NAKAGAWA S, 1991, Patent No. 430037

← 1 2 →