Synthesis, antioxidant, and antimicrobial activity of some novel N-substituted derivatives of 3-(benzo[b]thiophen-2-yl)-5-(3-[trifluoromethyl]styryl)-4,5-dihydro-1H-pyrazole

被引:1
|
作者
Pandy, Karthik Manikandan [1 ]
Krishnan, Radhakrishnan [2 ]
Paratharaj, Senthilkumar [1 ]
机构
[1] Solara Act Pharma Sci Ltd, Res Ctr, Synthet Dev, Chennai, Tamil Nadu, India
[2] Madurai Kamaraj Univ, Saraswathi Narayanan Coll Arts & Sci, Madurai, Tamil Nadu, India
关键词
OXIDATIVE STRESS; PYRAZOLINE; ANTICANCER; CU2+;
D O I
10.1002/jhet.4519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The new series of various N-substituted pyrazoline derivatives containing benzo[b]thiophene and styryl with trifluoromethyl substitution at meta- position were synthesized. Compound 1-(3-(benzo[b]thiophen-2-yl)-5-(3-[trifluoromethyl]styryl)-4,5-dihydro-1H-pyrazol-1-yl)-2-chloroethan-1-one (3b) was further substituted with various thiols. The structures of newly synthesized compounds were characterized by UV, IR, NMR, and Mass and had been screened for antioxidant and antimicrobial activity. The in vitro antioxidant screening revealed that hydroxyl radical scavenging (HRS) activities of compounds 3a, 3b, 3c, 3f, 3i, 3j, 4a, and 4c are stronger than the other compounds and the in vitro antimicrobial activities of the compounds were tested against Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis, Aspergillus flavus, and Aspergillus Niger. The compounds 3d and 3e exhibit good activity against P. mirabilis. Compounds 3a, 3b, 3c, 3 h, 3i, 3j, and 4a showed significant activity against S. aureus. Compounds 3e and 3f showed very good activity against A. flavus. Compounds 3e, 3f, and 4c showed good activity against A. Niger.
引用
收藏
页码:1790 / 1800
页数:11
相关论文
共 50 条
  • [1] Synthesis and Antimicrobial Activity of Some Novel Substituted 3-(Thiophen-2-yl)pyrazole-based Heterocycles
    Abdel-Wahab, Bakr F.
    Farahat, Abdelbasset A.
    Awad, Ghada E. A.
    El-Hiti, Gamal A.
    LETTERS IN DRUG DESIGN & DISCOVERY, 2017, 14 (11) : 1316 - 1323
  • [2] Ultrasound-Promoted Synthesis of 3-(Thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1carboximidamides and Anticancer Activity Evaluation in Leukemia Cell Lines
    dos Santos, Eric F. S.
    Cury, Nathalia M.
    do Nascimento, Tainara A.
    Raminelli, Cristiano
    Casagrande, Gleison A.
    Pereira, Claudio M. P.
    Simionatto, Euclesio
    Yunes, Jose A.
    Pizzuti, Lucas
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2017, 28 (02) : 217 - +
  • [3] MICROWAVE ASSISTED SYNTHESIS OF 3-(2-BENZOYL-6-HYDROXY-3-METHYL BENZO[b] FURAN-5-YL)-5-(ARYL)-4, 5-DIHYDRO-1H-PYRAZOLE CARBOTHIOAMIDES AND THEIR ANTIBACTERIAL ACTIVITY
    Ashok, D.
    Sudershan, K.
    Khalilullah, M.
    HETEROCYCLIC LETTERS, 2011, 1 (04): : 311 - 317
  • [4] Synthesis and antihepatotoxic activity of 5-(2,3-dihydro-1,4-benzodioxane-6-yl)-3-substituted-phenyl-4,5-dihydro-1H-pyrazole derivatives
    Khalilullah, Habibullah
    Khan, Shamshir
    Ahsan, Mohamed Jawed
    Ahmed, Bahar
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (24) : 7251 - 7254
  • [5] SYNTHESIS, PRECLINICAL EVALUATION AND ANTIDEPRESSANT ACTIVITY OF 5-SUBSTITUTED PHENYL-3-(THIOPHEN-2-YL)-4, 5-DIHYDRO-1H-PYRAZOLE-1-CARBOTHIOAMIDES
    Mathew, Bijo
    Suresh, Jerad
    Anbazhagan, S.
    EXCLI JOURNAL, 2014, 13 : 437 - 445
  • [6] Synthesis, characterization and antioxidant activities of novel N-substituted pyrazoline derivatives bearing 3-benzo[b]thiophene and 5-styryl substituents
    Krishnan, Radhakrishnan
    Pandy, Karthik Manikandan
    Paratharaj, Senthil Kumar
    Ray, Uttam Kumar
    INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (07): : 703 - 716
  • [7] Synthesis and evaluation of in vitro antiviral activity of 2-[3-(substituted phenyl)-4,5-dihydro-1H-5-pyrazolyl]benzofuran-3-yl chloride derivatives
    Yar, A. Shahar
    Abdullah, M. Mustaqeem
    Husain, A.
    Bhakht, M. Afroz
    De Clercq, Erik
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (04) : 949 - 956
  • [8] Synthesis and in vitro evaluation of antioxidant and anti-inflammatory activity of 3-[4,5-dihydro-(5-substituted phenyl)-1H-pyrazol-3-yl]-2H-chromen-2-one derivatives
    A. Bhatnagar
    P. K. Sharma
    N. Kumar
    A. Upadhyay
    Pharmaceutical Chemistry Journal, 2012, 46 : 482 - 487
  • [9] Synthesis and in vitro evaluation of antioxidant and anti-inflammatory activity of 3-[4,5-dihydro-(5-substituted phenyl)-1H-pyrazol-3-yl]-2H-chromen-2-one derivatives
    Bhatnagar, A.
    Sharma, P. K.
    Kumar, N.
    Upadhyay, A.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2012, 46 (08) : 482 - 487
  • [10] Synthesis, single crystal structure, DNA binding and antioxidant properties of 5-(4-(dimethylamino)phenyl)-3-(thiophen-2-yl)-pyrazoline-1-carbothioamide
    Rana, Manish
    Fatima, Aysha
    Siddiqui, Nazia
    Dar, Sajad Hussain
    Javed, Saleem
    Rahisuddin
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1261