Thienopyridone Antibacterials V [1]. Synthesis of Some N(7)-Azacyclohexyl-4-oxothieno[2,3-b]pyridine-5-carboxylic Acids and Related Congeners

被引：7

作者：

Al-Jaber, Hala I. ^{[2
]}

El-Abadelah, Mustafa M. ^{[2
]}

Sabri, Salim S. ^{[3
]}

Al-Tel, Taleb H. ^{[3
]}

Voelter, Wolfgang ^{[1
]}

机构：

[1] Univ Tubingen, Interfak Inst Biochem, D-72076 Tubingen, Germany

[2] Univ Jordan, Fac Sci, Dept Chem, Amman 11942, Jordan

[3] Univ Sharjah, Sharjah, U Arab Emirates

来源：

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2009年 / 64卷 / 11-12期

关键词：

4-Oxothieno[2,3-b]pyridines; 7-(N; N-Dimethylamino); 7-Azacyclohexyl Derivatives; 7-Chiral Alaninol / Phenylethylamine Moieties; Antibacterial Activity; 5-CARBOXYLIC ACIDS; INVITRO; AGENTS;

D O I：

10.1515/znb-2009-11-1249

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of N(7)-azacyclohexyl-4-oxo-4,7-dihydrothieno[2,3-b]-pyridine-5-carboxylic acids 9a-c, related congeners 9d-g and their methyl esters 8a-g were prepared by cyclization of the respective 2-[(2,5-dichlorothien-3-yl)carbonyl]-3-[(N(7)-azacyclyl/acyclic)amino]acrylates 7a-g. The latter intermediates are accessible from methyl 2-[(2,5-dichlorothien-3-yl)carbonyl]-3-ethoxyacrylate (6). Of the present series, the 7-(N,N-dimethylamino) derivative 9d exhibited good activity, especially against Klebsiella pneumoniae and Salmonella paratyphi A (MIC = 0.5 and 1.0 mu g mL(-1), respectively).

引用

页码：1625 / 1632

页数：8

共 35 条

[1] SYNTHESIS OF 7-ETHYL-4,7-DIHYDRO-4-OXO-2-(4-PYRIDINYL)THIENO[2,3-B]PYRIDINE-5-CARBOXYLIC ACID [J].

BACON, ER ;

DAUM, SJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (08) :1953-1955

[2]

BIERE H, 1976, LIEBIGS ANN CHEM, V11, P1972

[3]

BLASKIEWICZ P, 1976, Patent No. 2244477

[4] SYNTHESIS AND ANTI-BACTERIAL ACTIVITY OF 4,7-DIHYDRO-7-ETHYL-4-OXOTHIENO[2,3-B]PYRIDINE 5-CARBOXYLIC ACIDS [J].

BOMPART, J ;

GIRAL, L ;

MALICORNE, G ;

PUYGRENIER, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1988, 23 (05) :457-464

[5] SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF NEW 4,7-DIHYDRO 7-ETHYL 4-OXO (2,3-B)THIENO PYRIDINE 5-CARBOXYLIC ACIDS [J].

BOMPART, J ;

GIRAL, L ;

MALICORNE, G ;

PUYGRENIER, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (02) :139-145

[6]

BROVIC G, 1989, ACTA CRYSTALLOGR C, V45, P1983

[7]

DAIICHI SEIYAKU CO L, 1985, Patent No. 60034968

[8]

EGAWA H, 1986, CHEM PHARM BULL, V34, P4098

[9] Thienopyridinone antibacterials. Part II. Synthesis and antibacterial activity of some 2-chloro-7-cyclopropyl-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acids [J].

El-Abadelah, MM ;

Sabri, SS ;

Al-Ashqar, HA ;

Mion, P ;

Bompart, J ;

Calas, M .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 134 :21-29

[10] Thienopyridinone antibacterials:: Synthesis and antibacterial activity of some 7-aryl-2-chloro-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acids [J].

El-Abadelah, MM ;

Nazer, MZ ;

Okasha, SF ;

Calas, M ;

Bompart, J ;

Mion, P .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (01) :33-42

← 1 2 3 4 →