Synthesis and Cytostatic Activity of Substituted Derivatives of Sodium 1-Amino-2-cyano-1,6-dioxo-4-{[3-(ethoxycarbonyl)thiophen-2-yl]amino}hexa-2,4-dien-3-olates

被引：0

作者：

Gorbunova, I. A. ^{[1
,2
]}

Mitusova, K. A. ^{[1
]}

Parkhoma, K. Yu. ^{[3
]}

Sharavyova, Yu. O. ^{[3
]}

Makhmudov, R. R. ^{[3
,4
]}

Ustinova, O. Yu. ^{[4
]}

Denislamova, E. S. ^{[5
]}

Shipilovskikh, D. A. ^{[1
,5
]}

机构：

[1] Peter Great St Petersburg Polytech Univ, St Petersburg 195251, Russia

[2] ITMO Univ, St Petersburg 197101, Russia

[3] Perm State Univ, Perm 614990, Russia

[4] Fed Sci Ctr Med & Prevent Hlth Risk Management Tec, Perm 614045, Russia

[5] Perm Natl Res Polytech Univ, Perm 614990, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2024年 / 94卷 / 12期

基金：

俄罗斯科学基金会;

关键词：

Gewald thiophenes; 3-(thiophen-2-yl)iminofuran-2(3H)-ones; antitumor activity; toxicity; drugs; ANALGESIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ACUTE TOXICITY; RESISTANCE; DESIGN; STRATEGIES;

D O I：

10.1134/S1070363224120028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

AbstractA series of new substituted derivatives of sodium 1-amino-1,6-dioxo-2-cyano-4-{[3-(ethoxycarbonyl)thiophen-2-yl]amino}hexa-2,4-dien-3-olates was synthesized by the furan ring opening reaction of substituted 3-thienylimino-3H-furan-2-ones under the action of amide of cyanoacetic acid in the presence of sodium carbonate as a base. The cytotoxic effect on 4T1 breast cancer cells was studied and the acute toxicity of the obtained compounds was assessed. It was found that the obtained compounds have pronounced anticancer activity and are practically non-toxic drugs (hazard class IV).

引用

页码：3140 / 3148

页数：9

共 43 条

[1] Synthesis and antinociceptive activity of potassium 1-alkoxy-6-aryl-2-cyano-4-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]-thiophen-2-yl)amino]-1,6-dioxohexa-2,4-dien-3-olates
D. V. Lipin
V. M. Shadrin
S. K. Metlyakova
P. S. Silaichev
R. R. Makhmudov
D. A. Shipilovskikh
Russian Chemical Bulletin, 2025, 74 (4) : 1145 - 1152
[2] Synthesis of the substituted derivatives of sodium 5-aryl-5-oxo-3-[(thiophen-2-yl)amino]penta-1,3-dien-2-olates and evaluation of their antinociceptive activity in vivo
Gorbunova, I. A.
Parkhoma, K. Yu.
Kozlov, D. A.
Nikonov, I. P.
Denislamova, E. S.
Makhmudov, R. R.
Shipilovskikh, D. A.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (12) : 3669 - 3676
[3] Synthesis and Antinociceptive Activity of Substituted Derivatives of Potassium 1-Cyano-3-{(3-cyano-4,5,6,7-tetrahydrobenzo-[b]thiophen-2-yl)amino}-5-oxopenta-1,3-dien-2-olates
Kozlov, D. A.
Lipin, D. V.
Gorbunova, I. A.
Shipilovskikh, D. A.
Timin, A. S.
Silaichev, P. S.
Makhmudov, R. R.
Shadrin, V. M.
Shipilovskikh, S. A.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2024, 94 (05) : 1024 - 1030
[4] Synthesis and Hemostatic Activity of Substituted Potassium 1-Cyano-3-{(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino}-5-oxopenta-1,3-dien-2-olates
Lipin, D. V.
Kozlov, D. A.
Shadrin, V. M.
Parkoma, K. Yu.
Starkov, A. V.
Shipilovskikh, D. A.
Pulina, N. A.
Shipilovskikh, S. A.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (08) : 1322 - 1328
[5] 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
[6] Synthesis and anti-inflammatory activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]-4-oxobut-2-enamides
Gorbunova, I. A.
Okoneshnikova, E. A.
Makhmudov, R. R.
Shadrin, V. M.
Silaichev, P. S.
Shipilovskikh, S. A.
Shipilovskikh, D. A.
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (09) : 2758 - 2764
[7] Synthesis and antinociceptive activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]4-oxobut-2-enamides
Gorbunova, I. A.
Okoneshnikova, E. A.
Makhmudov, R. R.
Shipilovskikh, D. A.
Shadrin, V. M.
Silaichev, P. S.
Shipilovskikh, S. A.
RUSSIAN CHEMICAL BULLETIN, 2023, 72 (08) : 1905 - 1912
[8] 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
I. A. Gorbunova
I. P. Nikonov
R. R. Makhmudov
D. A. Shipilovskikh
P. S. Silaichev
S. A. Shipilovskikh
Russian Chemical Bulletin, 2023, 72 : 2255 - 2262
[9] 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
[10] Synthesis and antinociceptive activity of N-substituted 4-aryl-2-[(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino]4-oxobut-2-enamides
I. A. Gorbunova
E. A. Okoneshnikova
R. R. Makhmudov
D. A. Shipilovskikh
V. M. Shadrin
P. S. Silaichev
S. A. Shipilovskikh
Russian Chemical Bulletin, 2023, 72 : 1905 - 1912

← 1 2 3 4 5 →