Synthesis, Characterization and Antimicrobial Evaluation of Some New Schiff, Mannich and Acetylenic Mannich Bases Incorporating a 1,2,4-Triazole Nucleus

被引:25
作者
Aouad, Mohamed R. [1 ,2 ]
机构
[1] Taibah Univ, Dept Chem, Fac Sci, Al Madinah Al Munawarah 30002, Saudi Arabia
[2] Univ Sci & Technol Mohamed Boudiaf, Fac Sci, Dept Chem, Lab Chim & Electrochim Complexes Metall LCECM UST, Oran 31000, Algeria
关键词
Schiff bases; Mannich bases; acetylenic Mannich bases; 1,2,4-triazole; antimicrobial activity;
D O I
10.3390/molecules191118897
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of Schiff and Mannich bases derived from 4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione were synthesized. The alkylation of 4-phenyl-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione with propargyl bromide afforded the corresponding thiopropargylated derivative which upon treatment with the appropriate secondary amines in the presence of CuCl2 furnished the desired acetylenic Mannich bases. The synthesized compounds were characterized on the basis of their spectral (IR, H-1-and C-13-NMR) data and evaluated for their biological activities. Some of the compounds were found to exhibit significant antimicrobial activity.
引用
收藏
页码:18897 / 18910
页数:14
相关论文
共 22 条
[11]  
Kalluraya B, 2001, INDIAN J HETEROCY CH, V10, P239
[12]   SYNTHESIS AND ANTIMICROBIAL EVALUATION OF NOVEL OXA(THIA)DIAZOLYLQUINOLINES AND OXA(THIA)DIAZEPINO[7,6-B] QUINOLINES [J].
KHALIL, MA ;
ELSAYED, OA ;
ELSHAMY, HA .
ARCHIV DER PHARMAZIE, 1993, 326 (08) :489-492
[13]   Design, synthesis, and urease inhibition studies of a series of 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones [J].
Khan, Mahmood-ul-Hassan ;
Hameed, Shahid ;
Yasin, Khawaja A. ;
Akhtar, Tashfeen ;
Khan, Khalid M. .
MONATSHEFTE FUR CHEMIE, 2010, 141 (04) :479-484
[14]   Artemisinin derivatives bearing Mannich base group: Synthesis and antimalarial activity [J].
Li, Y ;
Yang, ZS ;
Zhang, H ;
Cao, BJ ;
Wang, FD ;
Zhang, Y ;
Shi, YL ;
Yang, JD ;
Wu, BA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (20) :4363-4368
[15]  
Merck V., 2001, MERCK INDEX, P320
[16]  
Merck V., 2001, MERCK INDEX, P3737
[17]   Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone [J].
Nithinchandra ;
Kalluraya, B. ;
Aamir, S. ;
Shabaraya, A. R. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :597-604
[18]   Metabolism of fluorine-containing drugs [J].
Park, BK ;
Kitteringham, NR ;
O'Neill, PM .
ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 2001, 41 :443-470
[19]  
SIDWELL RW, 1975, P SOC EXP BIOL MED, V148, P854
[20]  
Tang C.C., 1998, PESTICIDE CHEM