Synthesis of novel 2-[4-(4-substitutedbenzamido/phenylacetamido)phenyl]benzothiazoles as antimicrobial agents

被引:15
作者
Bolelli, Kayhan [1 ]
Yalcin, Ismail [1 ]
Ertan-Bolelli, Tugba [1 ]
Ozgen, Selda [2 ]
Kaynak-Onurdag, Fatma [2 ]
Yildiz, Ilkay [1 ]
Aki, Esin [1 ]
机构
[1] Ankara Univ, Dept Pharmaceut Chem, Fac Pharm, TR-06100 Ankara, Turkey
[2] Gazi Univ, Dept Pharmaceut Microbiol, Fac Pharm, TR-06330 Ankara, Turkey
关键词
Benzothiazole; Antibacterial activity; Antifungal activity; Multi-drug resistance; TOPOISOMERASE-II INHIBITORS; ANTITUMOR BENZOTHIAZOLES; BENZIMIDAZOLES; BENZOXAZOLES; DERIVATIVES; 3D-QSAR; ACID;
D O I
10.1007/s00044-011-9918-4
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of 2-[4-(4-substitutedbenzamido/phenylacetamido)phenyl] benzothiazole derivatives (6a-k) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Escherichia coli with their drug-resistant isolates and a yeast Candida albicans. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at minimum inhibitory concentration (MIC) values between 100 and 6.25 mu g/ml. Compounds 6d and 6k exhibited significant antibacterial activity showing 6.25 mu g/ml MIC values against drug-resistant S. aureus and P. aeruginosa isolates, respectively.
引用
收藏
页码:3818 / 3825
页数:8
相关论文
共 26 条
[1]   SYNTHESIS AND ORAL ANTIALLERGIC ACTIVITY OF CARBOXYLIC-ACIDS DERIVED FROM IMIDAZO[2,1-C][1,4]BENZOXAZINES, IMIDAZO[1,2-A]QUINOLINES, IMIDAZO[1,2-A]QUINOXALINES, IMIDAZO[1,2-A]QUINOXALINONES, PYRROLO[1,2-A]QUINOXALINONES, PYRROLO[2,3-A]QUINOXALINONES, AND IMIDAZO[2,1-B]BENZOTHIAZOLES [J].
AGER, IR ;
BARNES, AC ;
DANSWAN, GW ;
HAIRSINE, PW ;
KAY, DP ;
KENNEWELL, PD ;
MATHARU, SS ;
MILLER, P ;
ROBSON, P ;
ROWLANDS, DA ;
TULLY, WR ;
WESTWOOD, R .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1098-1115
[2]   Antitumor benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines [J].
Chua, MS ;
Shi, DF ;
Wrigley, S ;
Bradshaw, TD ;
Hutchinson, I ;
Shaw, PN ;
Barrett, DA ;
Stanley, LA ;
Stevens, MFG .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (03) :381-392
[3]  
Clinical and Laboratory Standards Institute, 2006, M100S16 CLSI
[4]  
Clinical and Laboratory Standards Institute (CLSI) (formerly NCCLS), 2006, M27A3 CLSI
[5]  
CLSI, 2006, informational supplement M100-S16, V26
[6]  
Dilworth JR, 2007, World Intellectual Property Organization, WO2007003944 A2, Patent No. 2007003944
[7]   Antimicrobial resistance in intensive care units [J].
Fridkin, SK ;
Gaynes, RP .
CLINICS IN CHEST MEDICINE, 1999, 20 (02) :303-+
[8]   THE USE OF POLYPHOSPHORIC ACID IN THE SYNTHESIS OF 2-ARYL-SUBSTITUTED AND 2-ALKYL-SUBSTITUTED BENZIMIDAZOLES, BENZOXAZOLES AND BENZOTHIAZOLES [J].
HEIN, DW ;
ALHEIM, RJ ;
LEAVITT, JJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (02) :427-429
[9]   Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs [J].
Hutchinson, I ;
Jennings, SA ;
Vishnuvajjala, BR ;
Westwell, AD ;
Stevens, MFG .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :744-747
[10]  
Kagaya T, 1996, J PHARMACOL EXP THER, V278, P243