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
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
收藏
页码:3140 / 3148
页数:9
相关论文
共 61 条
[1]   Benzothiazole a privileged scaffold for Cutting-Edges anticancer agents: Exploring drug design, structure-activity relationship, and docking studies [J].
Aayishamma, I ;
Matada, Gurubasavaraja Swamy Purawarga ;
Pal, Rohit ;
Ghara, Abhishek ;
Aishwarya, Nimmagadda Venkata Satya Sai ;
Kumaraswamy, B. ;
Hosamani, Ketan R. ;
V. Manjushree, B. ;
Haripriya, E. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2024, 279
[2]  
akomska I., 2014, J. Inorg. Biochem, V141, P188, DOI [10.1016/j.jinorgbio.2014.08.005, DOI 10.1016/J.JINORGBIO.2014.08.005]
[3]  
Archna S. P., 2020, BIOORG CHEM, V101, DOI [DOI 10.1016/j.bioorg.2020.104026, 10.1016/j.bioorg.2020.104026]
[4]  
Babushkina AA, 2022, RUSS J GEN CHEM+, V92, P18, DOI [10.1134/S1070363222010042, 10.31857/S0044460X2201005X]
[5]   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
[6]   Novel strategies for overcoming multildrug resistance in cancer [J].
Baguley, BC .
BIODRUGS, 2002, 16 (02) :97-103
[7]  
Belenkii M., 1963, Parameters of Quantitative Evaluation of Pharmacological Effect, P152
[8]   The Design, Synthesis, and Biological Activities of Pyrrole-Based Carboxamides: The Novel Tubulin Inhibitors Targeting the Colchicine-Binding Site [J].
Boichuk, Sergei ;
Galembikova, Aigul ;
Syuzov, Kirill ;
Dunaev, Pavel ;
Bikinieva, Firuza ;
Aukhadieva, Aida ;
Zykova, Svetlana ;
Igidov, Nazim ;
Gankova, Ksenia ;
Novikova, Maria ;
Kopnin, Pavel .
MOLECULES, 2021, 26 (19)
[9]   2-APCAs, the Novel Microtubule Targeting Agents Active against Distinct Cancer Cell Lines [J].
Boichuk, Sergei ;
Galembikova, Aigul ;
Bikinieva, Firuza ;
Dunaev, Pavel ;
Aukhadieva, Aida ;
Syuzov, Kirill ;
Zykova, Svetlana ;
Igidov, Nazim ;
Ksenofontov, Alexander ;
Bocharov, Pavel .
MOLECULES, 2021, 26 (03)
[10]   Bioactive compounds in kombucha: A review of substrate effect and fermentation conditions [J].
Bortolomedi, Bruna Milena ;
Paglarini, Camila Souza ;
Brod, Fabio Cristiano Angonesi .
FOOD CHEMISTRY, 2022, 385