Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent

Bimolendu Das; Chinmay Chowdhury; Deepak Kumar; Rupashree Sen; Rajneeta Roy; Padma Das; Mitali Chatterjee

doi:10.1016/j.bmcl.2010.09.126

Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent

Bioorg Med Chem Lett. 2010 Dec 1;20(23):6947-50. doi: 10.1016/j.bmcl.2010.09.126. Epub 2010 Oct 23.

Authors

Bimolendu Das¹, Chinmay Chowdhury, Deepak Kumar, Rupashree Sen, Rajneeta Roy, Padma Das, Mitali Chatterjee

Affiliation

¹ Indian Institute of Chemical Biology (CSIR), Kolkata, India.

PMID: 20974534
DOI: 10.1016/j.bmcl.2010.09.126

Abstract

A series of analogues of andrographolide, prepared through chemo-selective functionalization at C14 hydroxy, have been evaluated for in vitro cytotoxicities against human leukemic cell lines. Two of the analogues (6a, 9b) exhibited significant potency. Preliminary studies on structure-activity relationship (SAR) revealed that the α-alkylidene-γ-butyrolactone moiety of andrographolide played a major role in the activity profile. The structures of the analogues were established through spectroscopic and analytical data.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Diterpenes / pharmacology
Drug Screening Assays, Antitumor
Humans
Leukemia / drug therapy
Leukemia / pathology
Molecular Structure
Spectrum Analysis
Structure-Activity Relationship

Substances

Antineoplastic Agents
Diterpenes
andrographolide
4-Butyrolactone