Synthesis, characterization, and in vitro antimicrobial evaluation of new 5-chloro-8-bromo-3-aryl-1,2,4-triazolo[4,3-c]pyrimidines

被引:4
作者
Kumara, Basavapatna N. Prasanna [1 ]
Mohana, Kikkeri N. [1 ]
Mallesha, Lingappa [2 ]
机构
[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India
[2] JSS Coll Arts Commerce & Sci, PG Dept Chem, Mysore 570025, Karnataka, India
关键词
8-Bromo-2,4-dichloropyrimidine; Triazolopyrimidines; Iodobenzene diacetate; Antimicrobial activity; Oxidative cyclization; ANTIBACTERIAL; REAGENTS; IODINE;
D O I
10.1007/s00044-013-0656-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of new 5-chloro-8-bromo-3-aryl-1,2,4-triazolo[4,3-c]pyrimidines (4a-j) have been accomplished in excellent yields by the oxidative cyclization of pyrimidinylhydrazines (3a-j) of various aryl aldehydes with one equivalents of iodobenzene diacetate in methanol. The chemical structures of the synthesized compounds were confirmed by elemental analyses, FT-IR, H-1 NMR, C-13 NMR, and mass spectral studies. Ten new compounds (4a-j) were tested in vitro for their antimicrobial activity against clinically isolated strains. Variable and modest activities were observed against the investigated strains of bacteria and fungi. Compounds 4f, 4i, and 4j demonstrated good antimicrobial activity against all the tested microbial strains.
引用
收藏
页码:445 / 453
页数:9
相关论文
共 50 条
  • [31] Synthesis and Antimicrobial Evaluation of Chiral 3, 5-Diaryl-5, 6-dihydro-thiazolo[2, 3-c] [1,2,4]triazoles
    Tiwari, Pawankumar R.
    John, Marina E.
    Karnik, Anil, V
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (12) : 978 - 982
  • [32] Platinum(II) complexes with 5,7-disubstituted-1,2,4-triazolo [1,5-a]pyrimidines: Spectroscopical characterization and cytotoxic activity in vitro
    Lakomska, Iwona
    Fandzloch, Marzena
    Poplawska, Beata
    Sitkowski, Jerzy
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2012, 91 : 126 - 129
  • [33] Synthesis of thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones via their [1,2,4]triazolo[4,3-c]pyrimidine compounds as new ring systems by dimroth-type rearrangement
    Nagamatsu, Tomohisa
    Ahmed, Shoeb
    Hossion, Abugafar M. L.
    Ohno, Seiji
    HETEROCYCLES, 2007, 73 (01) : 777 - +
  • [34] Synthesis and Biological Evaluation of New 1,2,4-Triazolo[1,5-a] pyridine and 1,2,4-Triazolo[1,5-a] isoquinoline Derivatives Bearing Diphenyl Sulfide Moiety as Antimicrobial Agents
    El-Adasy, Abu-Bakr A.
    Hussein, Abd El-Haleem M.
    Ishak, Esam A.
    Hafiz, Ibrahim S. A.
    Gawish, Emad H.
    Elapasery, Morsy A.
    El-Gaby, Mohamed S. A.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2021, 64 (02): : 913 - 921
  • [35] Synthesis, conformational analysis and antimicrobial activity of 10-benzyl-1,2,4-triazolo[4,3-b]1,2,4-triazino[5,6-b]indole acyclo C-nucleoside analogs
    Nasr, Adel Z.
    Keshk, Reda M.
    Abdelrehim, El-Sayed M.
    Sallam, Asmaa S.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2025, 44 (06) : 433 - 455
  • [36] Copper(II) chloride mediated synthesis and DNA photocleavage activity of 1-aryl/heteroaryl-4-substituted-1,2,4-triazolo[4,3-a]quinoxalines
    Aggarwal, Ranjana
    Sumran, Garima
    Kumar, Virender
    Mittal, Ashwani
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) : 6083 - 6088
  • [37] Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1-c][1,2,4]triazolo[3,4-f][1,2,4]triazines
    El Azab, Islam H.
    Elkanzi, Nadia A. A.
    MOLECULES, 2020, 25 (06):
  • [38] Synthesis, Characterization and Antibacterial Evaluation of some New 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines as Potential Antibacterial Agents
    Sim, Kooi-Mow
    Teo, Kah-Cheng
    LETTERS IN DRUG DESIGN & DISCOVERY, 2018, 15 (07) : 733 - 743
  • [39] Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity
    Badr, Sahar M. I.
    Barwa, Rasha M.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (15) : 4506 - 4512
  • [40] Regioselective synthesis and oxidation of a new series of 6-nitro-4,5,6,7-tetrahydro-1,2,4-triazolo[1,5-a]pyrimidines
    Chirkov, D. D.
    Butorin, I. I.
    Eltsov, O. S.
    Slepukhin, P. A.
    Rusinov, V. L.
    RUSSIAN CHEMICAL BULLETIN, 2024, 73 (08) : 2370 - 2384