Synthesis and antitumor activities of novel bis-quinazolin-4(3H)-ones

被引:16
|
作者
Rahmannejadi, Nasrin [1 ,2 ]
Yavari, Issa [3 ]
Khabnadideh, Soghra [4 ]
机构
[1] Islamic Azad Univ, Dept Chem Sci, Tehran, Iran
[2] Islamic Azad Univ, Res Branch, Tehran, Iran
[3] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran
[4] Shiraz Univ Med Sci, Pharmaceut Sci Res Ctr, Shiraz, Iran
关键词
BREAST-CANCER; DERIVATIVES; QUINAZOLINONES; 2-AMINOBENZAMIDES;
D O I
10.1002/jhet.3749
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
With the aim of obtaining new antitumor agents, a series of bis-quinazolin-4(3H)-ones (3a-3 f) were designed and synthesized. These products contain 4-oxo-1,2,3,4-tetrahydro-quinazoline and 3H-quinazolin-4-one moieties linked together via a propyl chain. Cytotoxic activities of 3a-3 f were evaluated against lung adenocarcinoma (A549), breast carcinoma (MCF-7) and ovarian cancer (SKOV3) cell lines using MTT method. Cisplatin was used as a positive control. Among the tested compounds 3a, 3b, and 3e showed the best cytotoxic activities against all cancerous cell lines with IC50 values even less than cisplatin. Compounds 3d and 3f also showed desirable cytotoxic activities especially against A549 and MCF-7.
引用
收藏
页码:978 / 982
页数:5
相关论文
共 50 条
  • [31] Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst
    Davoodnia, A.
    Allameh, S.
    Fakhari, A. R.
    Tavakoli-Hoseini, N.
    CHINESE CHEMICAL LETTERS, 2010, 21 (05) : 550 - 553
  • [32] Straightforward synthesis of quinazolin-4(3H)-ones via visible light-induced condensation cyclization
    Sun, Wuji
    Ma, Xue
    Pang, Yuqi
    Zhao, Lifeng
    Zhong, Qidi
    Liu, Chunyan
    Fan, Qiangwen
    RSC ADVANCES, 2022, 12 (03) : 1494 - 1498
  • [33] Triflic Anhydride-Mediated Friedel-Crafts Arylation of Quinazolin-4(3H)-ones
    Yao, Zhenying
    Tang, Zhanyong
    Zhao, Depeng
    CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (03)
  • [34] Synthesis of acetyl deoxyvasicinone analogues from 2-(4-oxopentyl) quinazolin-4(3H)-ones via linear cyclizations
    Saebang, Yotsakorn
    Rukachaisirikul, Vatcharin
    Kaeobamrung, Juthanat
    TETRAHEDRON LETTERS, 2023, 121
  • [35] Formation of quinazolin-4(3H)-ones from N-sulfonoketenimines and 2-aminobenzamides
    Yavari, Issa
    Akbarzadeh, Somayeh
    Ghorbanzadeh, Meysam
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2024, 21 (4) : 1011 - 1019
  • [36] Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation
    Roberts, Bryan
    Liptrot, David
    Luker, Tim
    Stocks, Michael J.
    Barber, Catherine
    Webb, Nicola
    Dods, Robert
    Martin, Barrie
    TETRAHEDRON LETTERS, 2011, 52 (29) : 3793 - 3796
  • [37] FACILE AND EFFICIENT OXIDATION OF QUINAZOLINES INTO QUINAZOLIN-4(3H)-ONES BY PERACETIC ACID
    Jin, Jian-Wen
    Zhang, Lin
    Meng, Guang-Rong
    Zhu, Jian-Hua
    Zhang, Qian
    SYNTHETIC COMMUNICATIONS, 2014, 44 (03) : 346 - 351
  • [38] An efficient HCCP-mediated direct amination of quinazolin-4(3H)-ones
    Shen, Zhenlu
    He, Xiaofei
    Dai, Jialiang
    Mo, Weimin
    Hu, Baoxiang
    Sun, Nan
    Hu, Xinquan
    TETRAHEDRON, 2011, 67 (09) : 1665 - 1672
  • [39] CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones
    Mahdavi, Mohammad
    Asadi, Mehdi
    Khoshbakht, Mahsa
    Saeedi, Mina
    Bayat, Mohammad
    Foroumadi, Alireza
    Shafiee, Abbas
    HELVETICA CHIMICA ACTA, 2016, 99 (05) : 378 - 383
  • [40] Synthesis of novel glycosyl-1,2,3-1H-triazolyl methyl quinazolin-4(3H)-ones and their effect on GLUT4 translocation
    Ramakrishna, K. Kumar G.
    Thakur, Ravi Kumar
    Pasam, Venkata Reddy
    Pandey, Jyotsana
    Mahar, Rohit
    Shukla, Sanjeev K.
    Tamrakar, Akhilesh K.
    Tripathi, Rama Pati
    TETRAHEDRON, 2017, 73 (02) : 187 - 203