Reaction of Papaverine with Baran Diversinates<sup>TM</sup>
The reaction of papaverine with a series of Baran Diversinates<sup>TM</sup> 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 analogu...
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/21/3938 |
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doaj-2e5345c6703f47fd8f6bda7c3aaaf6a42020-11-25T02:32:55ZengMDPI AGMolecules1420-30492019-10-012421393810.3390/molecules24213938molecules24213938Reaction of Papaverine with Baran Diversinates<sup>TM</sup>Folake A. Egbewande0Mark J. Coster1Ian D. Jenkins2Rohan A. Davis3Griffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaGriffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaGriffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaGriffith Institute for Drug Discovery, Griffith University, Brisbane, QLD 4111, AustraliaThe reaction of papaverine with a series of Baran Diversinates<sup>TM</sup> 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 (<b>2</b>−<b>11</b>), 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 Diversinate<sup>TM</sup> reactions with this particular scaffold are discussed.https://www.mdpi.com/1420-3049/24/21/3938late-stage functionalizationsulfinatediversinate<sup>tm</sup>natural productmedicinal chemistrypapaverinescaffoldlibrarybiodiscovery |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Folake A. Egbewande Mark J. Coster Ian D. Jenkins Rohan A. Davis |
| spellingShingle |
Folake A. Egbewande Mark J. Coster Ian D. Jenkins Rohan A. Davis Reaction of Papaverine with Baran Diversinates<sup>TM</sup> Molecules late-stage functionalization sulfinate diversinate<sup>tm</sup> natural product medicinal chemistry papaverine scaffold library biodiscovery |
| author_facet |
Folake A. Egbewande Mark J. Coster Ian D. Jenkins Rohan A. Davis |
| author_sort |
Folake A. Egbewande |
| title |
Reaction of Papaverine with Baran Diversinates<sup>TM</sup> |
| title_short |
Reaction of Papaverine with Baran Diversinates<sup>TM</sup> |
| title_full |
Reaction of Papaverine with Baran Diversinates<sup>TM</sup> |
| title_fullStr |
Reaction of Papaverine with Baran Diversinates<sup>TM</sup> |
| title_full_unstemmed |
Reaction of Papaverine with Baran Diversinates<sup>TM</sup> |
| title_sort |
reaction of papaverine with baran diversinates<sup>tm</sup> |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2019-10-01 |
| description |
The reaction of papaverine with a series of Baran Diversinates<sup>TM</sup> 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 (<b>2</b>−<b>11</b>), 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 Diversinate<sup>TM</sup> reactions with this particular scaffold are discussed. |
| topic |
late-stage functionalization sulfinate diversinate<sup>tm</sup> natural product medicinal chemistry papaverine scaffold library biodiscovery |
| url |
https://www.mdpi.com/1420-3049/24/21/3938 |
| work_keys_str_mv |
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