Synthesis, Characterization and Antimicrobial Evaluation of Novel Imidazo[1,2-a]pyrazine-linked 1,2,3-Triazole Derivatives via a Click Chemistry Approach

被引:1
作者
Parmar, R. V. [1 ]
Vadodaria, M. S. [1 ]
机构
[1] Shree M&N Virani Sci Coll, Chem Res Lab, Rajkot 360005, India
关键词
antimicrobial activity; minimum inhibitory concentration; CuAAC; 1,4-disubstituted 1,2,3-triazoles; click chemistry; EPIDEMIOLOGY; DISCOVERY; ANALOGS;
D O I
10.1134/S1070428023110118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This work summarizes the results of the synthesis of imidazo[1,2-a]pyrazine-linked 1,2,3-triazole derivatives and provides evidence for the importance of this motif as a lead structure for novel drug discovery. The novel synthetic approach to imidazo[1,2-a]pyrazin-1,2,3-triazole derivatives, developed in this work, is based on the click chemistry approach. Nine novel hybrid compounds were synthesized and characterized by IR and H-1 and C-13 NMR spectroscopy, mass spectrometry, and elemental analysis. The synthesized products were tested for antimicrobial activity against E. coli, P. aeruginosa, E. aerogenes, B. megaterium, S. aureus, and B. subtilis bacterial strains and A. niger, and A. flavus fungal strains. The antimicrobial activity was evaluated in terms of the minimum inhibitory concentration (MIC). Some of the test compounds showed a high activity antibacterial and antifungal activity.
引用
收藏
页码:1927 / 1939
页数:13
相关论文
共 34 条
  • [11] The growing impact of click chemistry on drug discovery
    Kolb, HC
    Sharpless, KB
    [J]. DRUG DISCOVERY TODAY, 2003, 8 (24) : 1128 - 1137
  • [12] PIPERAZINYLIMIDAZO[1,2-A]PYRAZINES WITH SELECTIVE AFFINITY FOR INVITRO ALPHA-ADRENERGIC RECEPTOR SUBTYPES
    LUMMA, WC
    RANDALL, WC
    CRESSON, EL
    HUFF, JR
    HARTMAN, RD
    LYON, TF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (03) : 357 - 363
  • [13] Targeting Plasmodium PI(4)K to eliminate malaria
    McNamara, Case W.
    Lee, Marcus C. S.
    Lim, Chek Shik
    Lim, Siau Hoi
    Roland, Jason
    Nagle, Advait
    Simon, Oliver
    Yeung, Bryan K. S.
    Chatterjee, Arnab K.
    McCormack, Susan L.
    Manary, Micah J.
    Zeeman, Anne-Marie
    Dechering, Koen J.
    Kumar, T. R. Santha
    Henrich, Philipp P.
    Gagaring, Kerstin
    Ibanez, Maureen
    Kato, Nobutaka
    Kuhen, Kelli L.
    Fischli, Christoph
    Rottmann, Matthias
    Plouffe, David M.
    Bursulaya, Badry
    Meister, Stephan
    Rameh, Lucia
    Trappe, Joerg
    Haasen, Dorothea
    Timmerman, Martijn
    Sauerwein, Robert W.
    Suwanarusk, Rossarin
    Russell, Bruce
    Renia, Laurent
    Nosten, Francois
    Tully, David C.
    Kocken, Clemens H. M.
    Glynne, Richard J.
    Bodenreider, Christophe
    Fidock, David A.
    Diagana, Thierry T.
    Winzeler, Elizabeth A.
    [J]. NATURE, 2013, 504 (7479) : 248 - +
  • [14] Mechanistic applications of click chemistry for pharmaceutical drug discovery and drug delivery
    Meghani, Nilesh M.
    Amin, Hardik H.
    Leel, Beom-Jin
    [J]. DRUG DISCOVERY TODAY, 2017, 22 (11) : 1604 - 1619
  • [15] Synthesis of new thiazole-2, -4, and -5-yl-(amino)methylphosphonates and phosphinates: unprecedented cleavage of thiazole-2 derivatives under acidic conditions
    Olszewski, Tomasz Krzysztof
    Boduszek, Bogdan
    [J]. TETRAHEDRON, 2010, 66 (45) : 8661 - 8666
  • [16] Antifungal Drug Resistance: Mechanisms, Epidemiology, and Consequences for Treatment
    Pfaller, Michael A.
    [J]. AMERICAN JOURNAL OF MEDICINE, 2012, 125 (01) : S3 - S13
  • [17] A new and versatile one-pot strategy to synthesize alpha-bromoketones from secondary alcohols using ammonium bromide and oxone
    Rammurthy, Banothu
    Swamy, Peraka
    Naresh, Mameda
    Srujana, Kodumuri
    Durgaiah, Chevella
    Sai, Gajula Krishna
    Narender, Nama
    [J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (10) : 3710 - 3714
  • [18] Research on heterocyclic compounds .37. Synthesis and antiinflammatory activity of methyl-substituted imidazo[1,2-a]pyrazine derivatives
    Rimoli, MG
    Avallone, L
    deCaprariis, P
    Luraschi, E
    Abignente, E
    Filippelli, W
    Berrino, L
    Rossi, F
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (03) : 195 - 203
  • [19] Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO
  • [20] 2-4