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

被引:0
作者
Parkhoma, K. Yu. [1 ]
Davydenkova, E. D. [1 ]
Makhmudov, R. R. [1 ]
Gorbunova, I. A. [2 ]
Shipilovskikh, D. A. [1 ,3 ]
机构
[1] Perm State Univ, 15 Ul Bukireva, Perm 614990, Russia
[2] ITMO Univ, Build A,49 Kronverksky prosp, St Petersburg 197101, Russia
[3] Perm Natl Res Polytech Univ, 29 Komsomolsky Prosp, Perm 614990, Russia
关键词
Gewald thiophenes; 2,4-dioxobutanoic acids; 3-(thiophen-2-ylimino)furan-2(3H)-ones; antinociceptive activity; toxicity; in vivo studies; ANTIINFLAMMATORY ACTIVITY; DERIVATIVES; THIENOPYRIMIDINE; THIOPHENE; DESIGN;
D O I
10.1007/s11172-024-4452-y
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthetic procedure was developed and the scope of the substituted 4-(het)aryl-2-[(3-ethoxycarbonyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)amino]-4-oxobut-2-enoic acids was broadened. Antinociceptive activity and acute toxicity of the synthesized compounds were studied. It was found that the synthesized substituted acids show pronounced antinociceptive activity and were classified as being practically non-toxic.
引用
收藏
页码:3359 / 3366
页数:8
相关论文
共 44 条
[1]  
ADAMI E, 1956, ARCH INT PHARMACOD T, V107, P322
[2]   Thienopyrimidine derivatives exert their anticancer efficacy via apoptosis induction, oxidative stress and mitotic catastrophe [J].
Amawi, Haneen ;
Karthikeyan, Chandrabose ;
Pathak, Rekha ;
Hussein, Noor. ;
Christman, Ryann ;
Robey, Robert ;
Ashby, Charles R., Jr. ;
Trivedi, Piyush ;
Malhotra, Ashim ;
Tiwari, Amit K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 138 :1053-1065
[3]  
Babushkina AA, 2022, RUSS J GEN CHEM+, V92, P18, DOI [10.1134/S1070363222010042, 10.31857/S0044460X2201005X]
[4]   Efficient synthesis and evaluation of antiviral and antitumor activity of novel 3-phosphonylated thiazolo[3,2-a]oxopyrimidines [J].
Babushkina, Anastasia A. ;
Dogadina, Albina, V ;
Egorov, Dmitrij M. ;
Piterskaia, Julia L. ;
Shtro, Anna A. ;
Nikolaeva, Yulia, V ;
Galochkina, Anastasia, V ;
Kornev, Anton A. ;
Boitsov, Vitali M. .
MEDICINAL CHEMISTRY RESEARCH, 2021, 30 (12) :2203-2215
[5]  
Belenkii M.L., 1963, Elements of Quantitative Evaluation of Pharmacological Effect
[6]   Straightforward synthesis of novel spiroether derivatives [J].
Bobrovskaya, Olga V. ;
Russkih, Aleksandr A. ;
Yankin, Andrei N. ;
Dmitriev, Maksim V. ;
Bunev, Aleksandr S. ;
Gein, Vladimir L. .
SYNTHETIC COMMUNICATIONS, 2021, 51 (11) :1731-1741
[7]   2-Aminothiophene scaffolds: Diverse biological and pharmacological attributes in medicinal chemistry [J].
Bozorov, Khurshed ;
Nie, Li Fei ;
Zhao, Jiangyu ;
Aisa, Haji A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 140 :465-493
[8]   Multicomponent synthesis of chromophores - The one-pot approach to functional p-systems [J].
Brandner, Larissa ;
Mueller, Thomas J. J. .
FRONTIERS IN CHEMISTRY, 2023, 11
[9]   Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains [J].
Cvijetic, Ilija N. ;
Verbic, Tatjana Z. ;
de Resende, Pedro Ernesto ;
Stapleton, Paul ;
Gibbons, Simon ;
Juranic, Ivan O. ;
Drakulic, Branko J. ;
Zloh, Mire .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 143 :1474-1488
[10]   Synthesis, Intramolecular Cyclization, and Antinociceptive Activity of Substituted 2-[2-(4-Nitrobenzoyl)hydrazinylidene]-4-oxobut-2-enoic Acids [J].
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