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
    Alsubari, Abdulsalam
    Bouhfid, Rachid
    Essassi, El Mokhtar
    [J]. 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
    Amin, Kamelia M.
    Ismail, Magda M. F.
    Noaman, Eman
    Soliman, Dalia H.
    Ammar, Yousry A.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (20) : 6917 - 6923
  • [3] Quinolone activity against anaerobes
    Appelbaum, PC
    [J]. DRUGS, 1999, 58 (Suppl 2) : 60 - 64
  • [4] Synthesis and antimicrobial activity of novel quinoxaline derivatives
    Badran, Mohga M.
    Moneer, Ashraf A.
    Refaat, Hanan M.
    El-Malah, Afaf A.
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2007, 54 (02) : 469 - 478
  • [5] Chemistry, biological properties and SAR analysis of quinoxalinones
    Carta, A.
    Piras, S.
    Loriga, G.
    Paglietti, G.
    [J]. 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
    Castro, A
    Castaño, T
    Encinas, A
    Porcal, W
    Gil, C
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) : 1644 - 1652
  • [7] ANTIBACTERIAL ACTIVITIES OF NON-ANTIBIOTIC DRUGS
    CEDERLUND, H
    MARDH, PA
    [J]. 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
    Chen, CT
    Lin, JS
    Moturu, MVRK
    Lin, YW
    Yi, W
    Tao, YT
    Chien, CH
    [J]. CHEMICAL COMMUNICATIONS, 2005, (31) : 3980 - 3982
  • [10] Synthesis of quinoxaline derivatives from substituted acetanilides through intramolecular quaternization reactions
    de Castro, S
    Chicharro, R
    Arán, VJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (06): : 790 - 802