Synthesis and Antioxidant Activity of New Pyrazolo[1,5-a]Pyrimidine Derivatives Incorporating a Thiazol-2-yldiazenyl Moiety

被引:10
|
作者
El-Mekabaty, Ahmed [1 ]
Habib, Osman M. O. [1 ]
Moawad, Evelin B. [1 ]
Hasel, Ali M. [1 ]
机构
[1] Mansoura Univ, Dept Chem, Fac Sci, El Gomhoria St, ET-35516 Mansoura, Egypt
关键词
FACILE SYNTHESIS; DISAZO DYES; AGENTS;
D O I
10.1002/jhet.2492
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-(Thiazol-2-yldiazenyl)-1H-pyrazole-3,5-diamine (2) was prepared by the reaction of 2-thiazolylazomalononitrile (1) with hydrazine hydrate in boiling ethanol and used as key intermediate for the synthesis of polyfunctionally substitut ed pyrazolo[1,5-a]pyrimidines via its reactions with reagents having 1,3-dielectrophilic centers. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. Representative compounds of the synthesized products were tested and evaluated as antioxidant agents. The results revealed that compounds (3), (4), (5), and (9) displayed promising antioxidant activity compared to the activity of ascorbic acid.
引用
收藏
页码:1820 / 1826
页数:7
相关论文
共 50 条
  • [11] New One-Step Synthesis of Pyrazolo[1,5-a]pyrimidine and Pyrazolo[1,5-a]quinazoline Derivatives via Multicomponent Reactions
    Ghotekar, Bhausaheb K.
    Jachak, Madhukar N.
    Toche, Raghunath B.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (04) : 708 - 713
  • [12] Efficient Synthesis and Biological Evaluation of Some New Pyrazolo[1,5-a]pyrimidine Derivatives as Antimicrobial Activity
    Abbas, Hebat-Allah S.
    Ahmed, Eman H.
    Fouda, Ahmed M.
    CHEMISTRYSELECT, 2024, 9 (41):
  • [13] New routes to the synthesis of pyridazinone, ethoxypyridine, pyrazole and pyrazolo[1,5-a]pyrimidine derivatives incorporating a benzotriazole moiety (vol 37, pg 1617, 2000)
    Al-Omran, F
    El-Hay, OYA
    El-Khair, AA
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) : 791 - 791
  • [14] SYNTHESIS OF NEW PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES VIA CT-COMPLEXATION
    MOHAMED, NK
    IBRAHIM, YR
    HASSAN, AA
    MOURAD, AFE
    ARCHIV DER PHARMAZIE, 1993, 326 (04) : 245 - 247
  • [16] HALOGENATION OF SOME DERIVATIVES OF PYRAZOLO[1,5-A]PYRIMIDINE
    AUZZI, G
    CECCHI, L
    COSTANZO, A
    PECORIVETTORI, L
    BRUNI, F
    FARMACO-EDIZIONE SCIENTIFICA, 1979, 34 (09): : 743 - 750
  • [17] HETEROCYCLIC SYNTHESIS WITH NITRILES - SYNTHESES OF SOME NOVEL PYRAZOLO[1,5-A]PYRIMIDINE AND PYRROLO[2',3'-3,4]PYRAZOLO[1,5-A]PYRIMIDINE DERIVATIVES
    ABDELRAZEK, FM
    JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (03): : 475 - 478
  • [18] Synthesis and Antimicrobial Activity of New Dihydropyrazolo[1,5-a]pyrimidine Derivatives
    Joshi, K. A.
    Pandya, H. B.
    Mahida, A. K.
    Modasiya, I. J.
    Dubal, G. G.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2024, 50 (02) : 304 - 312
  • [19] Synthesis, In Vitro Antimicrobial and Cytotoxic Activities of Some New Pyrazolo[1,5-a]pyrimidine Derivatives
    Fouda, Ahmed M.
    Abbas, Hebat-Allah S.
    Ahmed, Eman H.
    Shati, Ali A.
    Alfaifi, Mohammad Y.
    Elbehairi, Serag Eldin I.
    MOLECULES, 2019, 24 (06)
  • [20] Design and synthesis of novel pyrazolo[1,5-a]pyrimidine derivatives bearing nitrogen mustard moiety and evaluation of their antitumor activity in vitro and in vivo
    Zhao, Mingxia
    Ren, Hongyu
    Chang, Jin
    Zhang, Diqin
    Yang, Yating
    He, Yong
    Qi, Chuanmin
    Zhang, Huabei
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 119 : 183 - 196