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The synthesis of Waltherione F and analogues with modifications at the 2- and 3-positions as potential antitrypanosomal agents

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posted on 2023-06-09, 15:48 authored by Brian Cox, Victor Zdorichenko, Romain Paumier, Thomas Whitmarsh-Everiss, Mark Roe
Chagas disease also know as American Trypanosomiasis (AT) is a tropical parasitic disease endemic in South America, is caused by Trypanosoma cruzi which is transmitted by the blood-sucking insect vectors called triatomine bugs. Quinoline alkaloids from the root extract of Waltheria indica are known to possess antitrypanosomal activity. Waltherione F 3, one of those alkaloids, was synthesised in 5 steps in 11% overall yield. A key step in the sequence utilised the Conrad-Limpach synthesis for the formation of the quinolin-4(1H)-one ring system. Our synthetic strategy was designed to enable the modification of the 2- and 3-positions of the scaffold, allowing the generation of a diverse library of analogues to support our on-going medicinal chemistry program that is looking for new agents to tackle this devastating disease.

History

Publication status

  • Published

File Version

  • Accepted version

Journal

Chemistry - A European Journal

ISSN

0947-6539

Publisher

Wiley

Issue

5

Volume

25

Page range

1286-1292

Department affiliated with

  • Biochemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2018-11-09

First Open Access (FOA) Date

2019-11-06

First Compliant Deposit (FCD) Date

2018-11-09

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