Synthesis and Antitumor Activities of Novel 5-amino-3-(halophenyl)-1-phenyl-1H-pyrazole-4-carbonitriles

被引:0
|
作者
Abd El-Wahab, Ashraf H. F. [1 ]
机构
[1] Jazan Univ, Fac Sci, Dept Chem, Jazan 2097, Saudi Arabia
关键词
Microwave; haloaromatic aldehydes; malononitrile; phenyl hydrazine and antitumor activities; MICROWAVE-ASSISTED SYNTHESIS; DNA GYRASE INHIBITORS; ANTIBACTERIAL ACTIVITY; ONE-POT; PYRAZOLE; DERIVATIVES; ANALOGS; 4-HYDROXYCOUMARIN; CATALYST; DESIGN;
D O I
10.2174/0115701794259226231023091306
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this work, a series of novel 3-(halophenyl)-1-phenyl-1H-pyrazole moieties have been synthesized. Their structures were characterized by IR, NMR, and MS spectroscopy, and the corresponding antitumor properties were also studied.Objectives This study aimed to synthesize a series of new 3-(halophenyl)-1-phenyl-1H-pyrazole moieties and survey the antitumor properties of these compounds.Materials and Methods 3-(halophenyl)-1-phenyl-1H-pyrazoles (4a-j) were prepared by reaction of phenyl hydrazine (3) with different halogen aromatic aldehydes 1a-j and malononitrile (2) in C2H5OH and piperidine. The reaction took place under microwave irradiation settings for two minutes at140 degrees C.Results Three human cancer cell lines were used as in vitro test subjects for compounds 4a - j. Three cell lines from mammals HeLa (a cell line for human cervical cancer), MCF-7 (a cell line for human breast cancer), and PC-3 (a cell line for human prostate cancer), all with 5-fluorouracil as the standard reference drug were used.Conclusion A series of novel 3-(halophenyl)-1-phenyl-1H-pyrazoles were synthesized in this work. All substances had their anticancer properties assessed.
引用
收藏
页码:72 / 78
页数:7
相关论文
共 50 条
  • [31] Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents
    Insuasty, Braulio
    Tigreros, Alexis
    Orozco, Fabian
    Quiroga, Jairo
    Abonia, Rodrigo
    Nogueras, Manuel
    Sanchez, Adolfo
    Cobo, Justo
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (14) : 4965 - 4974
  • [32] 5-(4-Fluorophenyl)-3-(naphthalen-1-yl)-1-phenyl-1H-pyrazole
    Jasril, Jasril
    Frimayanti, Neni
    Nurulita, Yuana
    Zamri, Adel
    Ikhtiarudin, Ihsan
    Guntur, Guntur
    MOLBANK, 2021, 2021 (01)
  • [33] Synthesis of 2,5,7-Triaryl-4,7(6,7)-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitriles by Reaction of 5(3)-Amino-3(5)-aryl-1H-pyrazole-4-carbonitriles with Chalcones
    Kolosov, Maksim A.
    Beloborodov, Dmitriy A.
    Kulyk, Olesia G.
    Orlov, Valeriy D.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 : E89 - E92
  • [34] 4-Bromo-3-methoxy-1-phenyl-1H-pyrazole
    Kleiziene, Neringa
    Arbaciauskiene, Egle
    Holzer, Wolfgang
    Sackus, Algirdas
    MOLBANK, 2009, (04)
  • [35] Synthesis and antimicrobial activities of some new 5-((3-(aryl)-1-phenyl-1H-pyrazol-4-yl)methylene)-3-phenylthiazolidine-2,4-diones
    Prakash, Om
    Aneja, Deepak Kumar
    Arora, Sanjiv
    Sharma, Chetan
    Aneja, K. R.
    MEDICINAL CHEMISTRY RESEARCH, 2012, 21 (01) : 10 - 15
  • [36] Vibrational and electronic absorption spectral studies of 5-amino-1-(4-bromophenyl)-3-phenyl-1-H-pyrazole
    Prasad, M. V. S.
    Chaitanya, Kadali
    Sri, N. Udaya
    Veeraiah, V.
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2012, 99 : 379 - 389
  • [37] Synthesis and Antimicrobial Activity of Novel 5-Amino-4-cyano-1H-pyrazole and Quinazolin-4(3H)-one Derivatives
    Abdel-Aal, Mohamed T.
    Abdel-Aleem, Abdel-Aleem H.
    Ibahim, Laila I.
    Zein, Ahmed L.
    ARCHIVES OF PHARMACAL RESEARCH, 2010, 33 (12) : 1891 - 1900
  • [38] An efficient and green reaction of isatins, 3-amino-1-phenyl-2-pyrazolin-5-one (3-amine-1H-pyrazole), and β-diketone in aqueous medium
    Wang, Zhansheng
    Xu, Hui
    Yan, Lirong
    Li, Qingyang
    Rong, Liangce
    MOLECULAR DIVERSITY, 2017, 21 (04) : 985 - 997
  • [39] COPPER(II) IONS MEDIATED CRYSTAL FORMATION OF 3-(3-HYDROXY PHENYL)-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE
    Banpurkar, Anita R.
    Wazalwar, Sach N. S.
    Perdih, Franc
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2020, 34 (03) : 589 - 596
  • [40] Synthesis, Antioxidant and Antidiabetic Activity of 1-[(5-Substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazole
    Kaushik, N.
    Kumar, N.
    Kumar, A.
    INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2016, 78 (03) : 351 - 359