Montmorillonite K10 clay promoted one-pot pseudo-five-component synthesis of 5-cyano-6-(phenylthio)-2-((1-phenylvinyl)imino)-4- aryl(or heteroaryl)-2H-pyran-3-carboxylic acid derivatives and their potential cytotoxic activity

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Chemical Sciences Pub Date : 2024-02-28 DOI:10.1007/s12039-023-02247-1
Pragati Sharma, Pragya Sinha, Nidhi Gupta
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Abstract

A facile green accessibility for the synthesis of novel, distinctly substituted 2H-pyran analogues employing montmorillonite K10 clay as a sustainable catalyst via a one-pot multi-component reaction involving various aldehydes, thiophenol and cyanoacetic acid with acetophenone has been developed. The noteworthy features of the current methodology are short reaction time (1.5-2 h), good yields (70-82%), convenient technique, operational simplicity, ease of work-up, and reusability of the catalyst up to two runs, adhering to green chemistry principles. A spectroscopic assessment validated the structure of all the synthesized products. This multi-component one-pot transformation conveniently forms two new C-C bonds, one C-O bond, one C-S bond, and two new rings with all reactants consumed efficiently. Additionally, all synthesized compounds have been evaluated for anti-cancer activity, and two of them were found to be efficacious against human breast cancer cell line, namely, MDA-MB 231.

Graphical Abstract

A green and efficient method has been developed for synthesizing novel 2H-pyran analogues using montmorillonite K10 clay as a catalyst. The method involves a one-pot multi-component reaction and yields high products (70–82%) while adhering to green chemistry principles. The synthesized compounds have shown efficacy against human breast cancer cell line MDA-MB 231.

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蒙脱石 K10 粘土促进 5-氰基-6-(苯硫基)-2-((1-苯基乙烯基)亚氨基)-4-芳基(或杂芳基)-2H-吡喃-3-羧酸衍生物的单锅伪五组分合成及其潜在的细胞毒性活性
本研究采用蒙脱石 K10 粘土作为可持续催化剂,通过涉及各种醛、噻吩酚和氰基乙酸与苯乙酮的单锅多组分反应,开发了一种合成新型、独特取代的 2H 吡喃类似物的简便绿色方法。该方法的显著特点是反应时间短(1.5-2 小时)、产率高(70-82%)、技术方便、操作简单、易于加工,而且催化剂可重复使用两次,符合绿色化学原则。光谱评估验证了所有合成产物的结构。这种多组分一锅转化法可以方便地形成两个新的 C-C 键、一个 C-O 键、一个 C-S 键和两个新的环,并有效地消耗了所有反应物。此外,对所有合成的化合物进行了抗癌活性评估,发现其中两种化合物对人类乳腺癌细胞系 MDA-MB 231 有疗效。该方法采用一锅多组分反应,产物收率高(70-82%),同时符合绿色化学原则。合成的化合物对人类乳腺癌细胞系 MDA-MB 231 具有疗效。
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来源期刊
Journal of Chemical Sciences
Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
3.10
自引率
5.90%
发文量
107
审稿时长
1 months
期刊介绍: Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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