Cox_et_al-2018-Chemistry_-_A_European_Journal.pdf (1.53 MB)
The synthesis of Waltherione F and analogues with modifications at the 2- and 3-positions as potential antitrypanosomal agents
journal contribution
posted on 2023-06-09, 15:48 authored by Brian Cox, Victor Zdorichenko, Romain Paumier, Thomas Whitmarsh-Everiss, Mark RoeChagas 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 JournalISSN
0947-6539Publisher
WileyExternal DOI
Issue
5Volume
25Page range
1286-1292Department affiliated with
- Biochemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2018-11-09First Open Access (FOA) Date
2019-11-06First Compliant Deposit (FCD) Date
2018-11-09Usage metrics
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