Synthesis and antimicrobial activity of new urea and thiourea derivatives of (2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methanamine

被引:20
作者
Vedavathi, Pandreti [1 ]
Sudhamani, Hasti [1 ]
Raju, Chamarthi Naga [1 ]
机构
[1] Sri Venkateswara Univ, Dept Chem, Tirupati 517502, Andhra Pradesh, India
关键词
Isocyanates; Isothiocyanates; (2 '-(1H-Tetrazol-5-yl)biphenyl-4-yl)methanamine; Antibacterial activity; Antifungal activity; II RECEPTOR ANTAGONISTS; BIOLOGICAL-ACTIVITY; NITRILE IMINES; GENERATION; DISCOVERY; POTENT;
D O I
10.1007/s11164-016-2823-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of a series of novel urea and thiourea derivatives of (2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methanamine (valsartan intermediate) (1) was accomplished by reaction of 1 with various substituted aryl isocyanates and aryl isothiocyanates in presence of N,N-dimethylpiperazine (DMP). All synthesized compounds were evaluated for their antibacterial and antifungal activities and their minimum inhibitory concentration (MIC) values determined. A few of the title compounds showed good in vitro antibacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli. The title compounds also exhibited high antifungal activity. The title compounds were characterized by infrared (IR), H-1 and C-13 nuclear magnetic resonance (NMR), and mass spectral data.
引用
收藏
页码:3251 / 3263
页数:13
相关论文
共 47 条
[1]  
Adeoye O., 2007, J AGR BIOL SCI, V2, P4
[2]   Potent, selective tetrahydro-beta-carboline antagonists of the serotonin 2B (5HT(2B)) contractile receptor in the rat stomach fundus [J].
Audia, JE ;
Evrard, DA ;
Murdoch, GR ;
Droste, JJ ;
Nissen, JS ;
Schenck, KW ;
Fludzinski, P ;
Lucaites, VL ;
Nelson, DL ;
Cohen, ML .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) :2773-2780
[3]  
Bary V., 1977, P 9 INT C, V8, P103
[4]  
BAUER AW, 1966, AM J CLIN PATHOL, V45, P493
[5]  
Blondelle S.E., 1998, PURE APPL CHEM, V70, P11
[6]   Thiourea inhibitors of herpes viruses.: Part 2:: N-benzyl-N′-arylthiourea inhibitors of CMV [J].
Bloom, JD ;
Dushin, RG ;
Curran, KJ ;
Donahue, F ;
Norton, EB ;
Terefenko, E ;
Jones, TR ;
Ross, AA ;
Feld, B ;
Lang, SA ;
DiGrandi, MJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (13) :3401-3406
[7]   GAS-PHASE REACTIONS .61. NITRILE IMINES RC=+N--N-SI(CH3)3 - OPTIMIZATION OF GAS-PHASE SYNTHESIS AND ASSIGNMENT OF THEIR PHOTOELECTRON-SPECTRA [J].
BOCK, H ;
DAMMEL, R ;
FISCHER, S ;
WENTRUP, C .
TETRAHEDRON LETTERS, 1987, 28 (06) :617-620
[8]  
Brown M., 1968, Chem. Abstr., 87299, Patent No. [US Patent 3, (1967), 338915, 3(]
[9]  
Burger A, 1991, Prog Drug Res, V37, P287
[10]  
Butler R.N., 1996, Comprehensive Heterocyclic Chemistry II, V4