Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids

被引:0
|
作者
I. A. Gorbunova
I. P. Nikonov
R. R. Makhmudov
D. A. Shipilovskikh
P. S. Silaichev
S. A. Shipilovskikh
机构
[1] Perm State National Research University,School of Physics and Engineering
[2] Perm National Research Polytechnic University,undefined
[3] ITMO University,undefined
来源
Russian Chemical Bulletin | 2023年 / 72卷
关键词
Gewald thiophenes; 2,4-dioxobutanoic acids; 3-iminofuran-2-ones; antinociceptive activity; toxicity; medications;
D O I
暂无
中图分类号
学科分类号
摘要
Synthesis and intramolecular cyclization of the substituted 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids were studied. It was found that the synthesized compounds underwent the intramolecular cyclization to give the substituted ethyl 4-(4-chlorophenyl)-2-{[2-oxofuran-3(2H)-ylidene]-amino}thiophene-3-carboxylates. Evaluation of the biological activity of the synthesized compounds showed that they have pronounced antinociceptive activity along with low toxicity.
引用
收藏
页码:2255 / 2262
页数:7
相关论文
共 50 条
  • [1] Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-2-{[4-(4-chlorophenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids
    Gorbunova, I. A.
    Nikonov, I. P.
    Makhmudov, R. R.
    Shipilovskikh, D. A.
    Silaichev, P. S.
    Shipilovskikh, S. A.
    RUSSIAN CHEMICAL BULLETIN, 2023, 72 (09) : 2255 - 2262
  • [2] SYNTHESIS, INTRAMOLECULAR CYCLIZATION AND ANTINOCICEPTIVE ACTIVITY OF 4-(HET)ARYL-2-{[3-(ETHOXYCARBONYL)-4-(4-R-PHENYL)THIOPHEN-2-YL]AMINO}4-OXOBUT-2-ENOIC ACIDS
    Nikonov, I. P.
    Sharavyeva, Yu. O.
    Makhmudov, R. R.
    Shipilovskikh, D. A.
    Gorbunova, I. A.
    IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 2024, 67 (11): : 22 - 32
  • [3] Synthesis, intramolecular cyclization, and antinociceptive activity of 4-(het)aryl-4-oxo-2-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]-thiophen-2-yl)amino]but-2-enoic acids
    Parkhoma, K. Yu.
    Davydenkova, E. D.
    Makhmudov, R. R.
    Gorbunova, I. A.
    Shipilovskikh, D. A.
    RUSSIAN CHEMICAL BULLETIN, 2024, 73 (11) : 3359 - 3366
  • [4] Synthesis, Intramolecular Cyclization, and Antinociceptive Activity of Substituted 2-[2-(4-Nitrobenzoyl)hydrazinylidene]-4-oxobut-2-enoic Acids
    Denisova, E., I
    Lipin, D., V
    Parkhoma, K. Yu
    Devyatkin, I. O.
    Shipilovskikh, D. A.
    Chashchina, S., V
    Makhmudov, R. R.
    Igidov, N. M.
    Shipilovskikh, S. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 57 (12) : 1955 - 1960
  • [5] Synthesis, Intramolecular Cyclization, and Antinociceptive Activity of Substituted 2-[2-(4-Nitrobenzoyl)hydrazinylidene]-4-oxobut-2-enoic Acids
    E. I. Denisova
    D. V. Lipin
    K. Yu. Parkhoma
    I. O. Devyatkin
    D. A. Shipilovskikh
    S. V. Chashchina
    R. R. Makhmudov
    N. M. Igidov
    S. A. Shipilovskikh
    Russian Journal of Organic Chemistry, 2021, 57 : 1955 - 1960
  • [6] Crystal structure and Hirshfeld surface analysis of (Z)-4-{[4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl]amino}-4-oxobut-2-enoic acid
    Simsek, Okan
    Dincer, Muharrem
    Dege, Necmi
    Saif, Eiad
    Yilmaz, Ibrahim
    Cukurovali, Alaaddin
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2022, 78 : 120 - +
  • [7] Synthesis of Substituted 4-(Thiophen-2-yl)nicotinonitriles
    Hakobyan, R. M.
    Attaryan, H. S.
    Melikyan, G. S.
    Hayotsyan, S. S.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (02) : 356 - 360
  • [8] Synthesis of Substituted 4-(Thiophen-2-yl)nicotinonitriles
    R. M. Hakobyan
    H. S. Attaryan
    G. S. Melikyan
    S. S. Hayotsyan
    Russian Journal of Organic Chemistry, 2020, 56 : 356 - 360
  • [9] Synthesis and Analgesic Activity of Substituted 4-(Het)aryl-4-oxo-2-thienylaminobut-2-enoic Acids
    S. A. Shipilovskikh
    R. R. Makhmudov
    D. Yu. Lupach
    P. T. Pavlov
    E. V. Babushkina
    A. E. Rubtsov
    Pharmaceutical Chemistry Journal, 2013, 47 : 366 - 370
  • [10] Synthesis and search for compounds with hemostatic activity in the series of 4-(het)aryl-4-oxobut-2-enoic acid derivatives
    Pulina, N. A.
    Kozhukhar, V. Yu.
    Kuznetsov, A. S.
    Rubtsov, A. E.
    Starkova, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (08) : 1497 - 1502