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

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2025-02-20 DOI:10.1007/s11172-024-4477-2

I. A. Gorbunova, K. Yu. Parkhoma, D. A. Kozlov, I. P. Nikonov, E. S. Denislamova, R. R. Makhmudov, D. A. Shipilovskikh

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引用次数: 0

Abstract

New substituted derivatives of 5-aryl-5-oxo-3-[(thiophen-2yl)amino]penta-1,3-dien-2-olates were synthesized by the reaction of the substituted 3-[(thiophen-2-yl)imino]furan-2(3H)-ones with cyanoacetic acid derivatives in the presence of sodium carbonate. The in vivo experiments revealed that the synthesized sodium salts possess pronounced antinociceptive activity that exceeded the activity of the reference drug (metamizole sodium). Sodium 1-amino-2-cyano-4-{[3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl]amino}-6-(4-methoxyphenyl)-1,6-dioxohexa-2,4-dien-3-olate demonstrated the highest activity exceeding that of metamizole sodium by ⩾1.5 times. Acute toxicity of all studied compounds (median lethal dose values (LD₅₀)) was greater than 1500 mg kg⁻¹ being six times higher than the LD₅₀ value for metamizole sodium.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.