Synthesis and biological activities of novel thieno[2,3-b]pyrrol-5-one derivatives: antioxidant and anticancer potential

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry Pub Date : 2025-05-04 DOI:10.1080/17415993.2025.2463482

M. Maya Pai , Basappa C. Yallur , Manjunatha D. Hadagali , Eliza Ahmed , Sheetal R. Batakurki , Raviraj Kusanur

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引用次数: 0

Abstract

In the present work, thiophene-substituted 4,6-dihydro-5H-thieno[2,3-b] pyrrol-5-ones (15a), (15b), (15c), and (15d) were synthesized. The key intermediate (13) was obtained by cyclization of 2-aminothiopheneaceate (6) using AlCl_3. Chloro-, bromo-, and methyl-substituted thiophene-2-carbaldehydes were coupled with (13) in aldol conditions to obtain compounds (15b), (15c), and (15d), respectively. Structural confirmation of all the synthesized compounds was done by ¹H NMR and studied for their antioxidant activity; compound (15a) showed 90.94% inhibition of DPPH free radical and 79.03% of ABTS free radical @ 500 μg/mL. Compounds (15a–d) were studied for their anticancer activity using MCF-7 cell lines, and the results of the MTT assay showed 78.23% for compound (15a). The IC₅₀ of (15a) was attained at 100 μg/mL for inhibiting the alpha amylase whereas 52.43 μg/mL for inhibiting EGFR Tyrosinase Kinase. The in-silico molecular docking studies showed the binding energy of compound (15a) at −5.3 kcal/mol for EGFR Tyrosinase Kinase (PDB - 5JEB) and −5.53 kcal/mol for α-amylase (PDB – 2MXX). Thus, compound (15a) exhibited good biological activities and further derivatization can lead to more potent molecules.

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新型噻吩[2,3-b]吡咯-5- 1衍生物的合成及其生物活性：抗氧化和抗癌潜力

本文合成了噻吩取代的4,6-二氢- 5h -噻吩[2,3-b]吡咯-5-酮（15a）、（15b）、（15c）和（15d）。关键中间体（13）由2-氨基噻吩酸酯(6)用AlCl3环化得到。氯代、溴代和甲基取代的噻吩-2-乙醛在醛醇条件下与（13）偶联，分别得到化合物（15b）、（15c）和（15d）。对合成的化合物进行了1H NMR结构确证，并对其抗氧化活性进行了研究；化合物（15a）在500 μg/mL时对DPPH自由基的抑制率为90.94%，对ABTS自由基的抑制率为79.03%。用MCF-7细胞系研究了化合物（15a - d）的抗癌活性，MTT实验结果显示化合物（15a）的抗癌活性为78.23%。抑制α淀粉酶的IC50为100 μg/mL，抑制EGFR酪氨酸激酶的IC50为52.43 μg/mL。硅基分子对接研究表明，化合物15a对EGFR酪氨酸激酶（PDB - 5JEB）和α-淀粉酶（PDB - 2MXX）的结合能分别为- 5.3 kcal/mol和- 5.53 kcal/mol。因此，化合物（15a）表现出良好的生物活性，进一步衍生化可以得到更有效的分子。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.