Synthesis, characterization and biological activity of new 3(4H)-quinazolinone derivatives

被引:0
|
作者
A. I. El-Shenawy
机构
[1] Benha University,Chemistry Department, Faculty of Science
来源
关键词
quinazolinylbenzoic acid; isothiocyanate cyclization; antimicrobial activity;
D O I
暂无
中图分类号
学科分类号
摘要
Quinazolinylbenzoic acid 1 was used as a precursor for synthesis of many heterocyclic systems. Ethyl 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate 2 upon reaction with hydrazine hydrate gave 4-[4-oxo-2-phenylquinazolin-3(4H)-yl]benzoate benzoylhydrazide 3. Compound 3 on treatment with 3-nitrobenzaldehyde, acetyl acetone, ethyl acetoacetate, and ammonium thiocyanate yielded compounds 4–8, respectively. Isothiocyanate 8 was used for the synthesis of other quinazoline derivatives 9–16 via the reactions with various reagents. All newly synthesized quinazolinone derivatives have been characterized by 1H NMR, IR, and mass spectroscopy. Most of the synthesized products were evaluated for their antibacterial and antifungal activities and some of those demonstrated high activity.
引用
收藏
页码:2067 / 2072
页数:5
相关论文
共 50 条
  • [31] Synthesis of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone and their cytotoxic activity
    Cao, Sheng-Li
    Feng, Yu-Ping
    Zheng, Xiao-Lin
    Jiang, Yu-Yang
    Zhang, Me
    Wang, Yue
    Xu, Meng
    ARCHIV DER PHARMAZIE, 2006, 339 (05) : 250 - 254
  • [32] Synthesis and Evaluation of the Antidepressant Activity of Quinoxaline-2,3(1H,4H)-dione Derivatives
    Fang, Ying-Quan
    Zhang, Hong-Jian
    Ren, Yang
    Quan, Zhe-Shan
    LATIN AMERICAN JOURNAL OF PHARMACY, 2018, 37 (01): : 170 - 181
  • [33] SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF SOME 1, 3, 4-THIADIAZOL DERIVATIVES
    Singh, Arvind Kumar
    Lohani, Mahfooz
    Singh, Umesh Pratap
    PAKISTAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2011, 24 (04) : 571 - 574
  • [34] Synthesis of 2-phenyl- and 2-benzyl derivatives of 4(3H)-quinazolinone with analgesic activity
    Kodonidi, I. P.
    Bicherov, A. V.
    Manvelyan, E. A.
    Kolodina, A. A.
    Bicherov, A. A.
    Manvelyan, M. M.
    Ivchenko, A. V.
    Vdovenko-Martynova, N. N.
    Navalieva, A. T.
    Manvelyan, M. M.
    PHARMACY & PHARMACOLOGY-FARMATSIYA I FARMAKOLOGIYA, 2023, 11 (01): : 89 - 100
  • [35] Synthesis and Antitumor Activity of 3-Hydrazone Quinazolinone Derivatives
    Liu Wwiqin
    Shao Lihui
    Li Chengpeng
    Zou Yayu
    Long Haitao
    Li Yan
    Ge Qiangsheng
    Wang Zhenchao
    Ouyang Guiping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (01) : 214 - 222
  • [36] Synthesis of new 4(3H)-Quinazolinone derivatives by reaction of 3-amino-2(1H)-thioxo-4(3H)-quinazolinone with selected substituted cinnamic acids and halogenoketones
    Nawrocka, Wanda P.
    Stasko, Jan J.
    Liszkiewicz, Hanna
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2008, 183 (06) : 1379 - 1387
  • [37] Synthesis of New 4(3H)-Quinazolinone Derivatives by Reaction of 3-Amino-2(1H)-thioxo-4(3H)-quinazolinone with Selected Chloroformates: Ammonolysis of 3-Ethoxycarbonylamino-2-ethoxycarbonylthio-4(3h)-quinazolinone, Part 21
    Nawrocka, Wanda P.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2009, 184 (02) : 261 - 274
  • [38] Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units
    Shao, Lihui
    Gan, Yiyuan
    Hou, Mi
    Tao, Shilin
    Zhang, Liqiong
    Wang, Zhenchao
    Ouyang, Guiping
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (07) : 1975 - 1982
  • [39] STUDIES ON 4(3H)-QUINAZOLINONE DERIVATIVES AS ANTIMALARIALS
    LAKHAN, R
    SINGH, OP
    SINGH, RL
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1987, 64 (05) : 316 - 318
  • [40] A review on some synthetic methods of 4(3H)-quinazolinone and benzotriazepine derivatives and their biological activities
    Abdelkhalek, Ahmed S.
    Abokull, Mansour E.
    Ibrahim, Samy M.
    Soltan, Mostafa K.
    Abdul-Malik, MokhtarA.
    Abdel-Raheem, Shaban A. A.
    ORGANIC COMMUNICATIONS, 2024, 17 (02) : 63 - 98