Issue 45, 2016
From the journal:

Organic & Biomolecular Chemistry

Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity†

Soumen Chakraborty,a   Gaurav Das,b   Surajit Ghoshb  and  Dipakranjan Mal*a  

* Corresponding authors

a Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur-721302, West Bengal, India
E-mail: dmal@chem.iitkgp.ernet.in

b Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, West Bengal, India

Abstract

An efficient and regioselective synthetic route to naphthoquinone/naphthoquinol–carbohydrate hybrids has been developed. It is based upon anionic annulation of 3-nucleofugalphthalides with an acrylate appended sugar moiety. In each of the annulations studied, the arene–carbohydrate hybrids were obtained in good to excellent yields. The in vitro cytotoxic activity of the synthetic naphthoquinone/naphthonol–carbohydrate hybrids were evaluated against the human cervical cancer cell line (HeLa), and a few of them were found to exhibit potent anticancer activity against the cell line.

Graphical abstract: Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity

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Article information

DOI
https://doi.org/10.1039/C6OB02154A
Article type
Paper
Submitted
04 Oct 2016
Accepted
19 Oct 2016
First published
19 Oct 2016

Org. Biomol. Chem., 2016,14, 10636-10647

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Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity

S. Chakraborty, G. Das, S. Ghosh and D. Mal, Org. Biomol. Chem., 2016, 14, 10636 DOI: 10.1039/C6OB02154A

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