Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents

Pravat Kumar* Parida; Abhijit* Sau; Tamashree Ghosh; Kuladip Jana; Kaushik Biswas; Sanghamitra Raha; Anup Kumar Misra

doi:10.1016/j.bmcl.2014.06.054

Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents

Pravat Kumar* Parida, Abhijit* Sau, Tamashree Ghosh, Kuladip Jana^*, Kaushik Biswas, Sanghamitra Raha, Anup Kumar Misra

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

38 Citations (Scopus)

Abstract

A series of glycosyl triazol linked 18β-glycyrrhetinic acid (GA) derivatives have been synthesized using 1,3-dipolar cycloaddition reaction of per-O-acetylated glycosyl azide derivatives (4a-h) with propargyl ester of 18β-glycyrrhetinic acid (GA) (2 and 3) following the concept of 'Click chemistry'. The synthesized triazole derivatives were de-O-acetylated to furnish compounds (7a-h and 8a-c) with free hydroxyl groups in the carbohydrate moieties, which were evaluated for their anticancer potential against human cervical cancer cells (HeLa) and normal kidney epithelial (NKE) cells. GA (1), compound 7d, compound 7g and compound 8c showed promising anticancer activities.

Original language	English
Pages (from-to)	3865-3868
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	24
Issue number	16
DOIs	https://doi.org/10.1016/j.bmcl.2014.06.054
Publication status	Published - 15 Aug 2014

Keywords

18β-Glycyrrhetinic acid
Anticancer agent
Carbohydrate
Click chemistry
Triazole

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title = "Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents",

abstract = "A series of glycosyl triazol linked 18β-glycyrrhetinic acid (GA) derivatives have been synthesized using 1,3-dipolar cycloaddition reaction of per-O-acetylated glycosyl azide derivatives (4a-h) with propargyl ester of 18β-glycyrrhetinic acid (GA) (2 and 3) following the concept of 'Click chemistry'. The synthesized triazole derivatives were de-O-acetylated to furnish compounds (7a-h and 8a-c) with free hydroxyl groups in the carbohydrate moieties, which were evaluated for their anticancer potential against human cervical cancer cells (HeLa) and normal kidney epithelial (NKE) cells. GA (1), compound 7d, compound 7g and compound 8c showed promising anticancer activities.",

keywords = "18β-Glycyrrhetinic acid, Anticancer agent, Carbohydrate, Click chemistry, Triazole",

author = "Parida, {Pravat Kumar*} and Abhijit* Sau and Tamashree Ghosh and Kuladip Jana and Kaushik Biswas and Sanghamitra Raha and Misra, {Anup Kumar}",

year = "2014",

month = aug,

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doi = "10.1016/j.bmcl.2014.06.054",

language = "English",

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T1 - Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents

AU - Parida, Pravat Kumar

AU - Sau, Abhijit

AU - Ghosh, Tamashree

AU - Jana, Kuladip

AU - Biswas, Kaushik

AU - Raha, Sanghamitra

AU - Misra, Anup Kumar

PY - 2014/8/15

Y1 - 2014/8/15

N2 - A series of glycosyl triazol linked 18β-glycyrrhetinic acid (GA) derivatives have been synthesized using 1,3-dipolar cycloaddition reaction of per-O-acetylated glycosyl azide derivatives (4a-h) with propargyl ester of 18β-glycyrrhetinic acid (GA) (2 and 3) following the concept of 'Click chemistry'. The synthesized triazole derivatives were de-O-acetylated to furnish compounds (7a-h and 8a-c) with free hydroxyl groups in the carbohydrate moieties, which were evaluated for their anticancer potential against human cervical cancer cells (HeLa) and normal kidney epithelial (NKE) cells. GA (1), compound 7d, compound 7g and compound 8c showed promising anticancer activities.

AB - A series of glycosyl triazol linked 18β-glycyrrhetinic acid (GA) derivatives have been synthesized using 1,3-dipolar cycloaddition reaction of per-O-acetylated glycosyl azide derivatives (4a-h) with propargyl ester of 18β-glycyrrhetinic acid (GA) (2 and 3) following the concept of 'Click chemistry'. The synthesized triazole derivatives were de-O-acetylated to furnish compounds (7a-h and 8a-c) with free hydroxyl groups in the carbohydrate moieties, which were evaluated for their anticancer potential against human cervical cancer cells (HeLa) and normal kidney epithelial (NKE) cells. GA (1), compound 7d, compound 7g and compound 8c showed promising anticancer activities.

KW - 18β-Glycyrrhetinic acid

KW - Anticancer agent

KW - Carbohydrate

KW - Click chemistry

KW - Triazole

UR - http://www.scopus.com/inward/record.url?scp=84905905997&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2014.06.054

DO - 10.1016/j.bmcl.2014.06.054

M3 - Article (Academic Journal)

C2 - 25027936

AN - SCOPUS:84905905997

SN - 0960-894X

VL - 24

SP - 3865

EP - 3868

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 16

ER -

Synthesis and evaluation of triazole linked glycosylated 18β-glycyrrhetinic acid derivatives as anticancer agents

Abstract

Keywords

UN SDGs

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