Synthesis and antimicrobial evaluation of some fused heterocyclic [1,2,4]triazolo [3,4-b][1,3,4]thiadiazole derivatives

被引:81
作者
Almajan, Gabriela Laura [1 ]
Barbuceanu, Stefania-Felicia [1 ]
Bancescu, Gabriela [2 ]
Saramet, Ioana [1 ]
Saramet, Gabriel [3 ]
Draghici, Constantin [4 ]
机构
[1] Fac Pharm, Dept Organ Chem, Bucharest 020956, Romania
[2] Fac Dent, Dept Microbiol, Bucharest 050051, Romania
[3] Fac Pharm, Pharmaceut Tech & Drug Ind Dept, Bucharest 020956, Romania
[4] Romanian Acad, CD Nenitescu Inst Organ Chem, Bucharest 060023, Romania
关键词
1,2,4]triazolo[3,4-b][1,3,4]thiadiazole; Cyclization; Diphenylsulfone moiety; Antimicrobial activity; ANTICONVULSANT; PRODUCTS;
D O I
10.1016/j.ejmech.2010.10.007
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of fused 1,2,4-triazoles with diphenylsulfone moiety are prepared utilizing 4-amino-5-[4-(4-X-phenylsulfonyl)phenyl]-4H-1,2,4-triazole-3-thiol 1 (X = H, Br). The latter on reaction with aromatic isothiocyanate in DMF, aromatic acid in POCI3 and CDI in dioxane gives five membered fused triazole derivatives 2a-c, 3a-c, 4a-g, 5a-g and 6a,b. The structures of newly synthesized compounds were confirmed on the basis of their elemental analysis and spectral data results (IR, H-1-and C-13 NMR). New synthesized compounds were screened for their antimicrobial activities. The preliminary results revealed that some of the compounds exhibited promising antimicrobial activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:6139 / 6146
页数:8
相关论文
共 24 条
[1]  
Almajan GL, 2005, REV CHIM-BUCHAREST, V56, P1182
[2]   Synthesis of some new 1,2,4-triazoles starting from isonicotinic acid hydrazide and evaluation of their antimicrobial activities [J].
Bayrak, Hacer ;
Demirbas, Ahmet ;
Demirbas, Neslihan ;
Karaoglu, Senguel Alpay .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (11) :4362-4366
[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]  
Cho NS, 1996, B KOR CHEM SOC, V17, P1170
[5]   Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities [J].
Demirbas, Ahmet ;
Sahin, Deniz ;
Demirbas, Neslihan ;
Karaoglu, Senguel Alpay .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (07) :2896-2903
[6]   Synthesis and antimicrobial activities of some new [1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines [J].
Demirbas, N ;
Demirbas, A ;
Karaoglu, SA ;
Çelik, E .
ARKIVOC, 2005, :75-91
[7]   Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo-{1,2,4]triazole derivatives [J].
Demirbas, N ;
Karaoglu, SA ;
Demirbas, A ;
Sancak, K .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (09) :793-804
[8]   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
[9]   Synthesis of new 2,5-disubstituted-1,3,4-thiadiazoles and preliminary evaluation of anticonvulsant and antimicrobial activities [J].
Dogan, HN ;
Duran, A ;
Rollas, S ;
Sener, G ;
Uysal, MK ;
Gülen, D .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (09) :2893-2898
[10]   Synthesis of 4-amino-5-(3-chlorobenzo[b]thien-2-yl)-3-mercapto-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and triazolo[3,4,b][1,3,4]thiadiazines under classical and microwave conditions [J].
El Ashry, E. S. H. ;
Kassem, A. A. ;
Abdel-Hamid, H. ;
Louis, F. F. ;
Khattab, Sh. A. N. ;
Aouad, M. R. .
ARKIVOC, 2006, :119-132