Synthesis and antibacterial activity of new spiro[thiadiazoline-quinoxaline] derivatives

被引:23
作者
Caleb, Ahoya A. [1 ]
Ballo, Daouda [1 ]
Rachid, Bouhfid [2 ]
Amina, Hancali [3 ]
Mostapha, Bousmina [2 ]
Abdelfettah, Zerzouf
Rajae, El Aouad [3 ]
El Mokhtar, Essassi [1 ,2 ]
机构
[1] Univ Mohammed V Agdal, Fac Sci, Lab Chim Organ Heterocycl, Av Ibn Battouta,BP 1014, Rabat, Morocco
[2] MASCIR Fdn, INANOTECH Inst Nanomat & Nanotechnol, Rabat 10100, Morocco
[3] Natl Inst Hyg, Microbiol Lab, Rabat, Morocco
关键词
3-Methylquinoxaline-2-thione; 1,3-dipolar cycloaddition; spiro[thiadiazoline-quinoxaline; antibacterial activity; ANTICANCER; ANTIFUNGAL;
D O I
10.3998/ark.5550190.0012.217
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1,3-dipolar cycloaddition of 3-methylquinoxaline-2-thione and their N-alkylated derivatives to diphenylnitrile imine is presented. Using this method, spiro[thiadiazoline-quinoxaline] derivatives as biologically interesting compounds were produced in high to excellent yields. These compounds have been characterized on the basis of their spectroscopic et spectrometric data (H-1 and C-13 NMR, IR, MS and X-ray). Antibacterial activity of the synthesized products has been studied by employing five bacterial strains. The compounds with ethyl group showed the best activity with MIC value of 32 mu g/mL against Streptococcus fasciens.
引用
收藏
页码:217 / 226
页数:10
相关论文
共 21 条
[1]   Synthesis of new oxindole derivatives containing an oxazolidin-2-one [J].
Alsubari, Abdulsalam ;
Bouhfid, Rachid ;
Essassi, El Mokhtar .
ARKIVOC, 2009, :337-346
[2]   New quinoxaline 1,4-di-N-oxides.: Part 1:: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides [J].
Amin, Kamelia M. ;
Ismail, Magda M. F. ;
Noaman, Eman ;
Soliman, Dalia H. ;
Ammar, Yousry A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (20) :6917-6923
[3]   Quinolone activity against anaerobes [J].
Appelbaum, PC .
DRUGS, 1999, 58 (Suppl 2) :60-64
[4]   Synthesis and antimicrobial activity of novel quinoxaline derivatives [J].
Badran, Mohga M. ;
Moneer, Ashraf A. ;
Refaat, Hanan M. ;
El-Malah, Afaf A. .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (02) :469-478
[5]   Chemistry, biological properties and SAR analysis of quinoxalinones [J].
Carta, A. ;
Piras, S. ;
Loriga, G. ;
Paglietti, G. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2006, 6 (11) :1179-1200
[6]   Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles [J].
Castro, A ;
Castaño, T ;
Encinas, A ;
Porcal, W ;
Gil, C .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1644-1652
[7]   ANTIBACTERIAL ACTIVITIES OF NON-ANTIBIOTIC DRUGS [J].
CEDERLUND, H ;
MARDH, PA .
JOURNAL OF ANTIMICROBIAL CHEMOTHERAPY, 1993, 32 (03) :355-365
[8]  
Chao W S, 2007, SOC INFORM DISPLAY, P802
[9]   Doubly ortho-linked quinoxaline/triarylamine hybrid as a bifunctional, dipolar electroluminescent template for optoelectronic applications [J].
Chen, CT ;
Lin, JS ;
Moturu, MVRK ;
Lin, YW ;
Yi, W ;
Tao, YT ;
Chien, CH .
CHEMICAL COMMUNICATIONS, 2005, (31) :3980-3982
[10]   Synthesis of quinoxaline derivatives from substituted acetanilides through intramolecular quaternization reactions [J].
de Castro, S ;
Chicharro, R ;
Arán, VJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (06) :790-802