14-Pivaloylandrographolide
Chemical Name: 2,2-Dimethylpropionic acid (3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methyleneperhydronaphthalen-1-yl]ethylidene]-5-oxotetrahydrofuran-3-yl ester
CAS No. 374539-84-1
项目整合开发状态: Biological Testing
项目研究机构: Dr. Reddy's Laboratories (Originator)
合成路线:Andrographolide (I) is protected as the acetonide (II) upon treatment with 2,2-dimethoxypropane and pyridinium p-toluenesulfonate.Esterification of the remaining free hydroxyl group of (II) with pivaloyl chloride provides the pivalate ester (III).The acetonide group of (III) is then removed by hydrolysis with 70 % AcOH to furnish the desired 14-pivaloyl andrographolide.(1,2)
📌 参考资料/链接：
参考文献标题:Novel anticancer cpds.: Process for their preparation and pharmaceutical compsns.containing them
文献作者:Chakrabarti,R.; Akella,V.; Nanduri,S.; Rajagopal,S.; Pothukuchi,S.; Pillai,S.B.K.(Dr.Reddy's Research Foundation)
参考来源:US 2002016363; US 6486196; WO 0185710
📄 详细内容
合成路线:Andrographolide (I) is protected as the acetonide (II) upon treatment with 2,2-dimethoxypropane and pyridinium p-toluenesulfonate.Esterification of the remaining free hydroxyl group of (II) with pivaloyl chloride provides the pivalate ester (III).The acetonide group of (III) is then removed by hydrolysis with 70 % AcOH to furnish the desired 14-pivaloyl andrographolide.(1,2)
参考文献标题:Synthesis and evaluation of novel ester analogs of andrographolide as potent anticancer agents
文献作者:Nanduri,S.; Nyavanandi,V.K.; Thunuguntla,S.S.R.; Kasu,S.; Pothukuchi,S.R.; Rajagopal,S.; Deevi,D.S.; Reka,A.K.; Ramanujam,R.; Akella,V.
参考来源:225th ACS Natl Meet (March 23 2003,New Orleans) 2003,Abst MEDI 93