Design, Synthesis, Antioxidant and Antibacterial Activities of Novel 2-((1-Benzyl-1H-1,2,3-Triazol-4-yl)methyl)-5-(2HChromen-3-yl)-2H-Tetrazoles

被引:14
作者
Srinivas, Burra [1 ]
Kumar, P. Vijay [1 ]
Reddy, P. Nagendra [1 ]
Venu, Sankeshi [2 ]
Shyam, Perugu [3 ]
Krupadanam, G. L. David [1 ]
机构
[1] Osmania Univ, Dept Chem, Nat Prod Lab, Hyderabad 500007, Telangana, India
[2] Osmania Univ, Dept Zool, Hyderabad 500007, Telangana, India
[3] Natl Inst Nutr, Hyderabad 500007, Telangana, India
关键词
2H-chromene; 1,2,3,4-tetrazoles; 1,2,3-triazoles; antioxidant activity; antibacterial activity; molecular docking studies; BETA-LAPACHONE; BIOLOGICAL-ACTIVITY; DERIVATIVES; INHIBITORS; TRIAZOLOTHIADIAZOLES;
D O I
10.1134/S1068162018020097
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
1,4-Disubstituted 1,2,3-triazole derivatives of 2H-chromene-3-tetrazoles synthesized regioselectively by copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click reaction were characterized by (HNMR)-H-1, C-13 NMR, IR, and mass spectral data. These derivatives were screened for in vitro antioxidant activity using DPPH radical, H2O2 scavenging, and iron chelating activity methods and also evaluated for in vitro antibacterial activities against E. coli and S. aureus bacterial strains. The MIC and IC50 values for all these compounds were found to match the docking scores and relevant binding energies with the receptor active sites. These results allows one to consider the compounds as leads for a new generation of antioxidant and antibacterial agents.
引用
收藏
页码:244 / 251
页数:8
相关论文
共 47 条
  • [1] Synthesis and anticonvulsant activity of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles
    Almasirad, A
    Tabatabai, SA
    Faizi, M
    Kebriaeezadeh, A
    Mehrabi, N
    Dalvandi, A
    Shafiee, A
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (24) : 6057 - 6059
  • [2] Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of some new 2-[(2,6-dichloroanilino) phenyl]acetic acid derivatives
    Amir, M
    Shikha, K
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (06) : 535 - 545
  • [3] Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
    Anderson, DR
    Hegde, S
    Reinhard, E
    Gomez, L
    Vernier, WF
    Lee, L
    Liu, S
    Sambandam, A
    Snider, PA
    Masih, L
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) : 1587 - 1590
  • [4] Atoni P. H., 2009, ANGEW CHEM INT EDIT, V48, P2126
  • [5] Baylis A. B., 1972, German Pat, Patent No. 2155113
  • [6] The ferric reducing ability of plasma (FRAP) as a measure of ''antioxidant power'': The FRAP assay
    Benzie, IFF
    Strain, JJ
    [J]. ANALYTICAL BIOCHEMISTRY, 1996, 239 (01) : 70 - 76
  • [7] Bhuiyan M.M.H., 2011, CHEM J, V1, P21
  • [8] ASYMMETRIC-SYNTHESIS .3. SYNTHESIS OF (2R)-(+)-2,3-DIHYDRO-2,6-DIMETHYL-4H-PYRAN-4-ONE, A HOMOLOG OF PHEROMONES OF A SPECIES IN THE HEPIALIDAE FAMILY
    BIANCHI, G
    TAVA, A
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1987, 51 (07): : 2001 - 2002
  • [9] Synthesis of potentially photoactivatable cournarin derivatives via a 1,3-dipolar cycloaddition
    Chenot, Elodie-Denise
    Rodriguez-Dominguez, Juan Carlos
    Hannewald, Paul
    Comel, Alain
    Kirsch, Gilbert
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1429 - 1435
  • [10] Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo
    de Andrade-Neto, VF
    Goulart, MOF
    da Silva, JF
    da Silva, MJ
    Pinto, MD
    Pinto, AV
    Zalis, MG
    Carvalho, LH
    Krettli, AU
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) : 1145 - 1149