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氨基磺酸促进的螺环氧化吲哚的一锅三组分合成及细胞毒性评价

Sulfamic acid promoted one-pot three-component synthesis and cytotoxic evaluation of spirooxindoles.

作者信息

Kamal Ahmed, Babu Korrapati Suresh, Vishnu Vardhan M V P S, Hussaini S M Ali, Mahesh Rasala, Shaik Siddiq Pasha, Alarifi Abdullah

机构信息

Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Catalytic Chemistry Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia.

Medicinal Chemistry and Pharmacology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

出版信息

Bioorg Med Chem Lett. 2015;25(10):2199-202. doi: 10.1016/j.bmcl.2015.03.054. Epub 2015 Mar 26.

Abstract

A simple, mild and efficient method for the synthesis of pyrazolopyridine based spirooxindoles by the three-component reaction has been developed using sulfamic acid (H2NSO3H) as a green catalyst. The method involves use of water as a solvent which makes it eco-friendly. The catalyst used is readily available and is prominent for short reaction time, operational simplicity and high yields. After completion of the reaction the catalyst could be recovered and reused for up to four cycles without loss in catalytic activity. Employing this method a library of 34 compounds has been synthesized and investigated for their cytotoxicity against a panel of three human cancer cell lines. Some of the compounds like 4o and 4p exhibited remarkable cytotoxicities with IC50 values of 0.35μM and 1.92μM against MDA-MB-231 cell line.

摘要

已经开发出一种简单、温和且高效的方法,以氨基磺酸(H2NSO3H)作为绿色催化剂,通过三组分反应合成基于吡唑并吡啶的螺环氧化吲哚。该方法使用水作为溶剂,使其具有环境友好性。所使用的催化剂易于获得,具有反应时间短、操作简单和产率高的特点。反应完成后,催化剂可以回收并重复使用多达四个循环,而不会损失催化活性。采用该方法合成了一个包含34种化合物的库,并研究了它们对三种人类癌细胞系的细胞毒性。一些化合物如4o和4p表现出显著的细胞毒性,对MDA-MB-231细胞系的IC50值分别为0.35μM和1.92μM。

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