A novel and efficient synthesis of 3-iodo substituted 1,8-naphthyridines by electrophilic cyclization of 2-amino nicotinaldehyde and their antimicrobial activity

被引:5
作者
Sakram, B. [1 ]
Ashok, K. [1 ]
Rambabu, S. [1 ]
Sonyanaik, B. [1 ]
Ravi, D. [1 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
2-aminonicotinaldehyde; electrophilic cyclization; iodine; 1,8-naphthyridine; antimicrobial activity; DERIVATIVES; AGENTS;
D O I
10.1134/S1070363217080266
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of substituted 1,8-naphthyridines based on 2-aminonicotinaldehyde under mild conditions is studied. Out of three electrophilic iodine sources (I-2, NIS, and ICl) studied, I-2 was determined to act most efficiently in the process. High overall yields were achieved for aliphatic substitution at the reaction center. All compounds were evaluated for antibacterial activity (Staphylococus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumonia) and anti-fungi activity (Aspergillus flavus and Fusarium oxysporum).
引用
收藏
页码:1794 / 1799
页数:6
相关论文
共 50 条
  • [31] 1,8-Naphthyridines VIII. Novel 5-aminoimidazo[1,2-a] [1,8]naphthyridine-6-carboxamide and 5-amino[1,2,4]triazolo[4,3-a] [1,8]naphthyridine-6-carboxamide derivatives showing potent analgesic or anti-inflammatory activity, respectively, and completely devoid of acute gastrolesivity
    Roma, Giorgio
    Di Braccio, Mario
    Grossi, Giancarlo
    Piras, Daniela
    Ballabeni, Vigilio
    Tognolini, Massimiliano
    Bertoni, Simona
    Barocelli, Elisabetta
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) : 352 - 366
  • [32] Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents
    Ramesh, P.
    Reddy, Ch. Sanjeeva
    Babu, K. Suresh
    Reddy, P. Muralidhar
    Rao, V. Srinivasa
    Parthasarathy, T.
    MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (10) : 3696 - 3709
  • [33] Synthesis, characterization and molecular docking studies of novel 2-amino 3-cyano pyrano[2,3H]chrysin derivatives as potential antimicrobial agents
    P. Ramesh
    Ch. Sanjeeva Reddy
    K. Suresh Babu
    P. Muralidhar Reddy
    V. Srinivasa Rao
    T. Parthasarathy
    Medicinal Chemistry Research, 2015, 24 : 3696 - 3709
  • [34] Novel synthesis of substituted N-(3-aryl-1,8-naphthyridin-2-yl) and N,N′-bis(3-aryl-1,8-naphthyridin-2-yl)benzene-1,4-diamines and 2-(4-((3-aryl-1,8-naphthyridin-2-yl)amino)phenyl)isoindoline-1,3-diones and their biological evaluation
    Ravi, D.
    Sakram, B.
    Ashok, K.
    Rambabu, S.
    Sonyanaik, B.
    Kurumanna, A.
    Madhu, P.
    SYNTHETIC COMMUNICATIONS, 2018, 48 (01) : 50 - 58
  • [35] Synthesis and antimicrobial activity of new 3-amino suphonyl[3′-chloro-4′-(substituted phenyl)-2′-oxo azetidine]indole
    Murugesh, K
    Saravanan, VS
    Leonard, JT
    Sonia, G
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (02) : 980 - 984
  • [36] SYNTHESIS OF 2-(SUBSTITUTED PHENYL)-3-[5-(2-OXO-2H-CHROMEN-3-YL)-1,3,4-OXADIAZOL-2-YL]-1,3-THIAZOLIDIN-4-ONES WITH ANTIMICROBIAL ACTIVITY
    Bhat, Mashooq A.
    Al-Omar, Mohammed A.
    Siddiqui, Nadeem
    ACTA POLONIAE PHARMACEUTICA, 2011, 68 (02): : 295 - 299
  • [37] Synthesis and antimicrobial activity of some novel substituted pyridazin-3(2H)-ones containing 1,3,4-thiadiazole moiety
    Sallam, Mohammed S.
    El-Hashash, Maher A.
    Guirguis, Dalal B.
    MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (02) : 369 - 380
  • [38] Efficient Synthesis of 3-Substituted 1,2,4-Triazolo[4,3-a]pyridine by [Bis(Trifluroacetoxy)iodo]benzene-Catalyzed Oxidative Intramolecular Cyclization of Heterocyclic Hydrazones
    Padalkar, Vikas S.
    Patil, Vikas S.
    Phatangare, Kiran R.
    Umape, Prashant G.
    Sekar, N.
    SYNTHETIC COMMUNICATIONS, 2011, 41 (06) : 925 - 938
  • [39] Synthesis and Antimicrobial Activity of 1-[2-(10-p-Chlorobenzyl) phenothiazinyl]-3-(substituted aryl)-2-propen-1-ones
    Upadhyay, R. K.
    Upadhyay, Megha S.
    Jain, S.
    E-JOURNAL OF CHEMISTRY, 2009, 6 : S254 - S258
  • [40] Synthesis and Antimicrobial Activity of N,N-Disubstituted 3-Allyloxy-1-amino-2-propanethiols
    M. A. Allakhverdiev
    A. B. Askerov
    Russian Journal of Applied Chemistry, 2003, 76 : 1280 - 1283