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

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

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

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.

Original language	English (US)
Pages (from-to)	6947-6950
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2010.09.126
State	Published - Dec 1 2010
Externally published	Yes

Keywords

Analogue
Andrographolide
Anti-cancer
Apoptosis
C14-ester

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2010.09.126

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

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.",

keywords = "Analogue, Andrographolide, Anti-cancer, Apoptosis, C14-ester",

author = "Bimolendu Das and Chinmay Chowdhury and Deepak Kumar and Rupashree Sen and Rajneeta Roy and Padma Das and Mitali Chatterjee",

note = "Funding Information: This work is supported by the CSIR net-work projects ( NWP 0009 and IAP 0001 ). Partial financial support from DST (project no: SR/S1/OC-42/2009 ), India is also gratefully acknowledged. B.D. and D.K. thank CSIR, New Delhi, for the award of fellowships. ",

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language = "English (US)",

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T1 - Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent

AU - Das, Bimolendu

AU - Chowdhury, Chinmay

AU - Kumar, Deepak

AU - Sen, Rupashree

AU - Roy, Rajneeta

AU - Das, Padma

AU - Chatterjee, Mitali

N1 - Funding Information: This work is supported by the CSIR net-work projects ( NWP 0009 and IAP 0001 ). Partial financial support from DST (project no: SR/S1/OC-42/2009 ), India is also gratefully acknowledged. B.D. and D.K. thank CSIR, New Delhi, for the award of fellowships.

PY - 2010/12/1

Y1 - 2010/12/1

N2 - 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.

AB - 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.

KW - Analogue

KW - Andrographolide

KW - Anti-cancer

KW - Apoptosis

KW - C14-ester

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DO - 10.1016/j.bmcl.2010.09.126

M3 - Article

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VL - 20

SP - 6947

EP - 6950

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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