（±）-硫代卡拉诺内酯A的合成、拆分及体外生物学评价。
A synthesis of (±)-thia-calanolide A, its resolution and in vitro biological evaluation.
作者信息
Chopade Anil U, Chopade Manojkumar U, Chanda Bhanu M, Sawaikar Dilip D, Sonawane Kiran B, Gurjar Mukund K
机构信息
Division of Organic Chemistry, National Chemical Laboratory, Pune 411008, India.
Department of Chemistry, University of Pune, Pune 411007, India.
出版信息
Arab J Chem. 2016 Nov;9:S1597-S1602. doi: 10.1016/j.arabjc.2012.04.027. Epub 2012 May 2.
Abstract
A synthesis of (±)-thia-calanolide A has been successfully accomplished starting from 3,5-dimethoxythiophenol , in six steps in an overall yield of 4.5%. The key reaction involved Friedel-Crafts tigloylation of 5,7-dihydroxy-4--propyl thiocoumarin employing an appropriate solvent of CS-PhNO in a ratio of 7:3. In its biological evaluation for anti-HIV activity, (±)-thia-calanolide A demonstrated comparatively less activity with calanolide A and its synthetic analogue aza-calanolide. Further, (±)-3 has been resolved by chiral HPLC to (+) and (-)-.
摘要
从3,5-二甲氧基苯硫酚出发，已成功完成了(±)-硫代卡拉诺内酯A的合成，共六步反应，总产率为4.5%。关键反应是在7:3的CS-PhNO适当溶剂中，对5,7-二羟基-4-丙基硫代香豆素进行傅克惕各酰化反应。在其抗HIV活性的生物学评价中，(±)-硫代卡拉诺内酯A与卡拉诺内酯A及其合成类似物氮杂卡拉诺内酯相比，活性相对较低。此外，(±)-3已通过手性高效液相色谱法拆分为(+)和(-)-异构体。
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