Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydroxybenzoyl)-1H-pyrazoles and pyrazolyl benzo[d]oxazoles

被引：52
|
作者：
Gadakh, Amol V. [1 ]
Pandit, Chetan [2 ]
Rindhe, Sahebrao S. [1 ]
Karale, Bhausaheb K. [3 ]
机构：
[1] Univ Pune, PG Dept Chem, New Arts Sci & Commerce Coll, Ahmednagar 414003, India
[2] Aurigene Discovery Technol Ltd, Bangalore 560100, Karnataka, India
[3] Univ Pune, Dept Chem, Radhabai Kale Mahila Mahavidyalaya, Ahmednagar 414003, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 18期
关键词：
Synthesis; Hydroxybenzoyl pyrazoles and benzoxazoles; Antimicrobial activities; Antifungal; Antibacterial; HETEROCYCLIC-SYSTEMS; FACILE SYNTHESIS; AGENTS; DERIVATIVES; NUCLEOPHILES; BENZOXAZOLES; RESISTANCE; CHEMISTRY;
D O I：
10.1016/j.bmcl.2010.07.019
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of fluorine containing 4-(substituted-2-hydroxybenzoyl) pyrazoles and pyrazolyl benzo[d]oxazoles were synthesized and evaluated for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Bacillus subtilis and antifungal activity against Candida albicans. The antibacterial activities were expressed as the minimum inhibitory concentration (MIC50) in mu g/ml. The compounds 1-(3,4-difluorophenyl)-4-(5-fluoro-2-hydroxybenzoyl)-1H-pyrazole (4b), oxime derivatives such as 1-(3,4-difluorophenyl)-1H-pyrazol-4-yl)(2-hydroxy-4-methylphenyl)methanone oxime (5b) and (5-chloro-2-hydroxyphenyl)(1-(3,4-difluorophenyl)-1H-pyrazol-4-yl)methanone oxime (5e) exhibited promising activities against tested bacterial strains. Except compound 1-(3,4-difluorophenyl)-4-(2-hydroxybenzoyl)-1H-pyrazole (4d), none of the other compounds showed promising antifungal activity. (C) 2010 Published by Elsevier Ltd.
引用
收藏
页码：5572 / 5576
页数：5
相关论文
共 50 条
  • [1] Nano-SnCl4/SiO2 as a Catalyst for One-Pot Synthesis of Substituted 1H-Pyrazoles as Antifungal and Cytotoxic Agents
    Khabnadideh, Soghra
    Faghih, Zeinab
    Zamani, Leila
    Zomorodian, Kamiar
    Mirjalili, Bi Bi Fatemesh
    Moradi, Hadi
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (06) : 459 - 465
  • [2] Evaluation of antioxidant activity and toxicity of sulfur- or selenium-containing 4-(arylchalcogenyl)-1H-pyrazoles
    de Oliveira, Daniela Hartwig
    Sabedra Sousa, Fernanda Severo
    Birmann, Paloma Taborda
    Pesarico, Ana Paula
    Alves, Diego
    Jacob, Raquel Guimaraes
    Savegnago, Lucielli
    CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 2020, 98 (07) : 441 - 448
  • [3] Synthesis, evaluation of antimicrobial activity, and molecular modeling of novel 2-((4-(2H-benzo[d] [1,2,3] triazol-2-yl)piperidin-1-yl)methyl)-5-substituted phenyl-1,3,4-oxadiazoles
    Vankadari, Srinivas Rao
    Mandala, Devender
    Pochampalli, Jalapathi
    Tigulla, Parthasarathy
    Valeru, Anil
    Thampu, Rajakomuraiah
    MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (12) : 5912 - 5919
  • [4] Synthesis of 2-substituted-6-(4H-1,2,4-triazol-4-yl)benzo[d]oxazoles as potential anticonvulsant agents
    Wei, Cheng-Xi
    Guan, Li-Ping
    Jia, Jing-Hao
    Chai, Kyu-Yun
    Quan, Zhe-Shan
    ARCHIVES OF PHARMACAL RESEARCH, 2009, 32 (01) : 23 - 31
  • [5] Synthesis, antimicrobial, anticancer and QSAR studies of 1-[4-(substituted phenyl)-2-(substituted phenyl azomethyl)-benzo[b]-[1,4]diazepin-1-yl]-2-substituted phenylaminoethanones
    Verma, Deepak
    Kumar, Pradeep
    Narasimhan, Balasubramanian
    Ramasamy, Kalavathy
    Mani, Vasudevan
    Mishra, Rakesh Kumar
    Majeed, Abu Bakar Abdul
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (08) : 2882 - 2896
  • [6] Synthesis and antimicrobial activity of 2-substituted [4-(1,3,4-oxadiazol-2-yl methyl)] phthalazin-1(2H)-one derivatives
    Sridhara, Ajjanna M.
    Reddy, Kallam R. Venugopala
    Keshavayya, Jathi
    Goud, Palusa Sanath Kumar
    Somashekar, Bankavadi C.
    Bose, Prosenjit
    Peethambar, Sanenahalli K.
    Gaddam, Satish Kumar
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) : 4983 - 4989
  • [7] Synthesis and antimicrobial activity of novel 1H-benzo[d]imidazole-aryl sulfonamide/amide derivatives
    Jadhav, Rahul, I
    Kedar, Nathrao A.
    Chavan, Kamlesh H.
    INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (02): : 184 - 191
  • [8] Synthesis and Antimicrobial Activity of Some Novel Substituted 1,2,4-Triazoles Bearing 1,3,4-Oxadiazoles or Pyrazoles
    Kalhor, Mehdi
    Mobinikhaledi, Akbar
    Dadras, Akbar
    Tohidpour, Maryam
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (06) : 1366 - 1370
  • [9] Synthesis and Antimicrobial Activity of 2-(4-(Hydroxyalkyl)-1H-1,2,3-triazol-1-yl)-N-substituted propanamides
    Kaushik, C. P.
    Luxmi, Raj
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3618 - 3625
  • [10] An Efficient Synthesis, Characterization and Antimicrobial Screening of N-substituted 2-(piperidin-4-yl)-2H-benzo[d] [1,2,3] Triazoles
    Pochampalli, Jalapathi
    Mandala, Devender
    Umapathireddy, Nalla
    Rajakomuraiah, Pompu
    LETTERS IN DRUG DESIGN & DISCOVERY, 2012, 9 (05) : 471 - 478
12345