Synthesis and Antiproliferative Screening of Some Heterocycles Derived from 4-((5-Chloro-3-Methyl-1-Phenyl-1H-Pyrazol-4-yl)Methylene)-2-Phenyloxazol-5(4H)-One

被引：7
|
作者：
Youssef, Youssef M. [1 ]
Azab, Mohammad E. [1 ]
Elsayed, Galal A. [1 ]
El-Sayed, Amira A. [1 ]
El-Helw, Eman A. E. [1 ]
机构：
[1] Ain Shams Univ, Fac Sci, Dept Chem, Cairo 11566, Egypt
来源：
POLYCYCLIC AROMATIC COMPOUNDS | 2023年 / 43卷 / 08期
关键词：
Antiproliferative; oxazolone; triazinone; pyrazole; triazole thione; RAPID COLORIMETRIC ASSAY; PYRAZOLE DERIVATIVES; ANTITUMOR; SYSTEMS; INHIBITION; SURVIVAL; SCAFFOLD; GROWTH; ACID;
D O I：
10.1080/10406638.2022.2130373
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new series of pyrazole derivatives was synthesized starting from the pyrazole-based oxazolone derivative 3. The activity of compound 3 toward some mono- and bidentate nucleophiles was investigated. Some of the synthesized compounds were screened for their antiproliferative activity against colon and breast cancer cell lines. The results of the biological assay revealed that the triazinone derivative 13 was the most potent against the two HCT116 and MCF7 cell lines since it showed IC50 = 8.37 +/- 0.5 mu M and 3.81 +/- 0.2 mu M, respectively, as compared to the reference drug doxorubicin (IC50 = 5.23 +/- 0.3 and 4.17 +/- 0.2 mu M, respectively).
引用
收藏
页码：7152 / 7163
页数：12
相关论文
共 50 条
  • [21] 4-[(Z)-(2-Furyl)(2-naphthylamino)methylene)]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
    Li, Jing
    Li, Jin-Zhou
    Li, Jing-Qi
    Zhang, Heng-Qiang
    Li, Jia-Min
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1824 - U2678
  • [22] 2-(Benzoylamino)-3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)acrylic acid
    Kaushik, Darpan
    Verma, Tarawanti
    Madaan, Kapish
    MOLBANK, 2011, (02)
  • [23] 4-[(2-Benzoyl-4-chlorophenyl)diazenyl]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
    Bahreni, Zaker
    Rahmani, Hossein
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O510 - U1705
  • [24] (Z)-4-[(2-Aminoanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
    Lu, Rong
    Xia, Hua
    Lu, Xingqiang
    Zhao, Shunsheng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2701 - +
  • [25] Synthesis of novel 5-substituted-6-methyl-4-[5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl]-3,4-dihydropyrimidin-2(1H)-ones
    Kumar, Rakesh
    Malik, Sakshi
    Chandra, Ramesh
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2007, 39 (01) : 101 - 106
  • [26] 3-Methyl-1-phenyl-4-[(phenyl)(2-phenylhydrazin-1-yl)methylidene]-1H-pyrazol-5(4H)-one
    Idemudia, Omoruyi G.
    Sadimenko, Alexander P.
    Afolayan, Anthony J.
    Hosten, Eric C.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1280 - +
  • [27] Synthesis, DFT, and eco-friendly insecticidal activity of some N-heterocycles derived from 4-((2-oxo-1,2-dihydroquinolin-3-yl) methylene)-2-phenyloxazol-5(4H)-one
    Ghareeb, Eman A.
    Mahmoud, Naglaa F. H.
    El-Bordany, Eman A.
    El-Helw, Eman A. E.
    BIOORGANIC CHEMISTRY, 2021, 112
  • [28] N-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)carbonyl]-N′-(4-hydroxy-phenyl)thiourea
    Du, Haitang
    Du, Haijun
    An, Ying
    Li, Shengnan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1404 - U1477
  • [29] Hydrogen-bonded chains in 3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(4-methoxyphenyl)-propenone and 3-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(3,4,5-trimethoxyphenyl)propenone
    Trilleras, J
    Quiroga, J
    Cobo, J
    Low, JN
    Glidewell, C
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O414 - O416
  • [30] 4-{[1-(Methoxycarbonyl)ethylamino](phenyl)methylidene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
    Zhu, HL
    Zhang, X
    Song, YJ
    Xu, HZ
    Dong, M
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2387 - O2388
12345