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
[1]   4-thiazolidinones: Novel inhibitors of the bacterial enzyme MurB [J].
Andres, CJ ;
Bronson, JJ ;
D'Andrea, SV ;
Deshpande, MS ;
Falk, PJ ;
Grant-Young, KA ;
Harte, WE ;
Ho, HT ;
Misco, PF ;
Robertson, JG ;
Stock, D ;
Sun, YX ;
Walsh, AW .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) :715-717
[2]  
[Anonymous], 1999, MOD DRUG DISCOV
[3]   Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities [J].
Bayrak, Hacer ;
Demirbas, Ahmet ;
Karaoglu, Senguel Alpay ;
Demirbas, Neslihan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1057-1066
[4]   Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents [J].
Demirbas, N ;
Ugurluoglu, R ;
Demirbas, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (12) :3717-3723
[5]   Interactions of azole antifungal agents with the human breast cancer resistance protein (BCRP) [J].
Gupta, Anshul ;
Unadkat, Jashvant D. ;
Mao, Qingcheng .
JOURNAL OF PHARMACEUTICAL SCIENCES, 2007, 96 (12) :3226-3235
[6]  
HASSAN E, 1983, PHARMAZIE, V38, P833
[7]   Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles [J].
Holla, BS ;
Veerendra, B ;
Shivananda, MK ;
Poojary, B .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (7-8) :759-767
[8]  
Holla BS, 2002, EUR J MED CHEM, V37, P511
[9]   Important fluorinated drugs in experimental and clinical use [J].
Ismail, FMD .
JOURNAL OF FLUORINE CHEMISTRY, 2002, 118 (1-2) :27-33
[10]  
Jorgensen J. H., 1995, CLIN MICROBIOLOGY