Synthesis, In Vitro and In Silico Antibacterial Evaluation of 4,5-Dihydro-1H-Indazoles

被引:2
|
作者
Khan, Rasool [1 ]
Shah, Faiza [1 ]
Salman, Muhammad [1 ]
Khan, Zahid [1 ]
Tavman, Aydin [2 ]
机构
[1] Univ Peshawar, Inst Chem Sci, Peshawar 25000, Pakistan
[2] Instanbul Univ, Dept Chem, Istanbul, Turkey
来源
CHEMISTRYSELECT | 2017年 / 2卷 / 29期
关键词
4,5-dihydro-1H-indazole; pentane-2,4-dione; 1,5-diaryl; 4-acetyl cyclohexen-3-one; In-vitro anti-bacterial potential; Docking studies; BIOLOGICAL EVALUATION; TRYPANOSOMA-CRUZI; MOLECULAR DOCKING; DRUG DISCOVERY; INDAZOLES; AGENTS; DERIVATIVES; DESIGN; CHALCONES; CONDENSATION;
D O I
10.1002/slct.201701244
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis and evaluation of in-vitro and in-silico anti-bacterial potential of a series of 4, 5-dihydro-1H-indazoles is reported here. The synthesis of the target 4,5-dihydro-1H-indazoles was accomplished by reacting 1,5-diaryl,4-acetyl cyclohexen-3-one with hydrazine hydrate and selected hydrazides. All the synthesized compounds were evaluated for their anti-bacterial potential against Escherichia coli, Proteus vulgaris, Staphylococcus aureus and Salmonella typhimurium. Among the synthesized indazoles, N,N-dimethyl-4-(3-methyl-6-phenyl-4,5-dihydro-1H-indazol-4-yl)aniline and 3-methyl-4-(3-nitrophenyl)-1,6-diphenyl-4,5-dihydro-1H-indazole exhibited highest antimicrobial activity against Salmonella typhimurium i.e. MIC50 = 3.85 and 4.12 mg/ml respectively. Docking studies were also carried out to provide an insight into binding interaction with the active site of respective enzyme.
引用
收藏
页码:9364 / 9368
页数:5
相关论文
共 50 条
  • [31] Synthesis, characterisation, and in vitro antibacterial evaluation of a new class of 2-substituted-4-methyl-7,8-dihydro-5H-pyrimido[4,5-d]thiazolo[3,2-a]pyrimidines
    Etemadi, Yasaman
    Shiri, Ali
    Eshghi, Hossein
    Akbarzadeh, Marzieh
    Saadat, Kayvan
    Mozafari, Sarinasadat
    Beyzaei, Hamid
    Moghaddam-Manesh, Mohammadreza
    JOURNAL OF CHEMICAL RESEARCH, 2016, (10) : 600 - 603
  • [32] Synthesis, characterization and biological evaluation of novel azo fused 2,3-dihydro-1H-perimidine derivatives: In vitro antibacterial, antibiofilm, anti-quorum sensing, DFT, in silico ADME and Molecular docking studies
    Nagasundaram, Nagarajan
    Govindhan, Chinnasamy
    Sumitha, Sivagiri
    Sedhu, Nagarajan
    Raguvaran, Krishnan
    Santhosh, Sigamani
    Lalitha, Appaswami
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1248
  • [33] Thiazolo[4,5-d]pyrimidines: synthesis and antibacterial evaluation
    Rahimizadeh, Mohammad
    Bakavoli, Mehdi
    Shiri, Ali
    Faridnia, Reyhaneh
    Pordeli, Parvaneh
    Oroojalian, Fatemeh
    HETEROCYCLIC COMMUNICATIONS, 2011, 17 (1-2) : 43 - 47
  • [34] QUINAZOLINE-PURINE DERIVATIVES AS ANTIDIABETICS: SYNTHESIS, IN- SILICO AND IN-VITRO EVALUATION
    Alam, Faruk
    Kemisetti, Durgaprasad
    Dey, Biplab Kumar
    Parameshwar, R.
    Chandrasekar, M. J. N.
    Azam, Afzal
    HETEROCYCLIC LETTERS, 2023, 13 (01): : 185 - 203
  • [35] C-vinylation of enolates with acetylenes in a one-pot synthesis of 4,5-dihydro-1H-pyrazole-1-carbothioamides
    Schmidt, E. Yu
    Tatarinova, I. V.
    Trofimov, B. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (01) : 136 - 138
  • [36] SYNTHESIS OF DERIVATIVES OF 5-(4,5-DIHYDRO-1H-3-PYRAZOLYL)-3,4-DIHYDRO-2(1H)-PYRIMIDONE
    Kolosov, M. A.
    Orlov, V. D.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) : 873 - 875
  • [37] Microwave-assisted green synthesis of 4,5-dihydro-1H-pyrazole-1-carbothioamides in water
    Farmani, Hamid Reza
    Mosslemin, Mohammad Hossein
    Sadeghi, Bahareh
    MOLECULAR DIVERSITY, 2018, 22 (03) : 743 - 749
  • [38] Synthesis and evaluation of antibacterial activity of 7-alkyloxy-4,5-dihydro-imidazo[1,2-a]quinoline derivatives
    Sun, Xian-Yu
    Wu, Rui
    Wen, Xiang
    Guo, Li
    Zhou, Chang-Ping
    Li, Jian
    Quan, Zhe-Shan
    Bao, Jun
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 : 451 - 455
  • [39] Synthesis of derivatives of 5-(4,5-dihydro-1H-3-pyrazolyl)-3,4-dihydro-2(1H)-pyrimidone
    M. A. Kolosov
    V. D. Orlov
    Chemistry of Heterocyclic Compounds, 2009, 45 : 873 - 875
  • [40] Synthesis and in vitro antimicrobial evaluation of novel fluorine-containing 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-1H-pyrazoles and 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-isoxazoles
    Chundawat, Tejpal Singh
    Sharma, Nutan
    Bhagat, Sunita
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (03) : 1350 - 1359