An efficient synthesis of [1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel thiazapodophyllotoxin analogues with potential anticancer activity

Tuanjie Li; Ting Lu; Chenxia Yu; Changsheng Yao

doi:10.1016/j.bmcl.2015.02.047

An efficient synthesis of [1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel thiazapodophyllotoxin analogues with potential anticancer activity

Bioorg Med Chem Lett. 2015 Apr 1;25(7):1417-9. doi: 10.1016/j.bmcl.2015.02.047. Epub 2015 Feb 27.

Authors

Tuanjie Li¹, Ting Lu¹, Chenxia Yu¹, Changsheng Yao²

Affiliations

¹ School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, PR China.
² School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, PR China. Electronic address: csyao@jsnu.edu.cn.

PMID: 25759030
DOI: 10.1016/j.bmcl.2015.02.047

Abstract

A catalyst-free synthesis of 6,9-dihydro-[1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel analogues of podophyllotoxins was developed by a three-component reaction of aldehydes, ethyl 2,4-dioxotetrahydrothiophene-3-carboxylate and 3,4-(methylenedioxy)aniline. This methodology not only provides new chemical library for the screening of anticancer activity, but also features excellent isolated yields, short reaction time, simple work up procedure and little environmental impact.

Keywords: Multicomponent synthesis; Potential anticancer activity; Thiazapodophyllotoxin.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Benzodioxoles / chemical synthesis
Benzodioxoles / chemistry
Benzodioxoles / pharmacology*
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Heterocyclic Compounds, 4 or More Rings / chemistry
Heterocyclic Compounds, 4 or More Rings / pharmacology*
Molecular Structure
Podophyllotoxin / chemical synthesis*
Podophyllotoxin / chemistry
Quinolines / chemical synthesis
Quinolines / chemistry
Quinolines / pharmacology*

Substances

Antineoplastic Agents
Benzodioxoles
Heterocyclic Compounds, 4 or More Rings
Quinolines
Podophyllotoxin