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Open AccessFeature PaperArticle

Reaction of Papaverine with Baran DiversinatesTM

Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, Australia
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Academic Editor: John C. D’Auria
Molecules 2019, 24(21), 3938; https://doi.org/10.3390/molecules24213938
Received: 30 September 2019 / Revised: 24 October 2019 / Accepted: 28 October 2019 / Published: 31 October 2019
(This article belongs to the Special Issue Advances in Plant Alkaloid Research)
The reaction of papaverine with a series of Baran DiversinatesTM is reported. Although the yields were low, it was possible to synthesize a small biodiscovery library using this plant alkaloid as a scaffold for late-stage C–H functionalization. Ten papaverine analogues (211), including seven new compounds, were synthesized. An unexpected radical-induced exchange reaction is reported where the dimethoxybenzyl group of papaverine was replaced by an alkyl group. This side reaction enabled the synthesis of additional novel fragments based on the isoquinoline scaffold, which is present in numerous natural products. Possible reasons for the poor yields in the DiversinateTM reactions with this particular scaffold are discussed. View Full-Text
Keywords: late-stage functionalization; sulfinate; DiversinateTM; natural product; medicinal chemistry; papaverine; scaffold; library; biodiscovery late-stage functionalization; sulfinate; DiversinateTM; natural product; medicinal chemistry; papaverine; scaffold; library; biodiscovery
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MDPI and ACS Style

Egbewande, F.A.; Coster, M.J.; Jenkins, I.D.; Davis, R.A. Reaction of Papaverine with Baran DiversinatesTM. Molecules 2019, 24, 3938. https://doi.org/10.3390/molecules24213938

AMA Style

Egbewande FA, Coster MJ, Jenkins ID, Davis RA. Reaction of Papaverine with Baran DiversinatesTM. Molecules. 2019; 24(21):3938. https://doi.org/10.3390/molecules24213938

Chicago/Turabian Style

Egbewande, Folake A.; Coster, Mark J.; Jenkins, Ian D.; Davis, Rohan A. 2019. "Reaction of Papaverine with Baran DiversinatesTM" Molecules 24, no. 21: 3938. https://doi.org/10.3390/molecules24213938

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