Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

Ashish P. Vartak; A. Gabriela Deaciuc; Linda P. Dwoskin; Peter A. Crooks

doi:10.1016/j.bmcl.2010.04.117

Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

Ashish P. Vartak, A. Gabriela Deaciuc, Linda P. Dwoskin, Peter A. Crooks

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition.

Original language	English (US)
Pages (from-to)	3584-3587
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	20
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2010.04.117
State	Published - 2010

Bibliographical note

Funding Information:
The authors would like to thank the National Institutes of Health , NIDA Grant DA013519 for financial support.

Keywords

Dopamine transport
Lobeline analogs
VMAT2

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10.1016/j.bmcl.2010.04.117

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title = "Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2",

abstract = "Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition.",

keywords = "Dopamine transport, Lobeline analogs, VMAT2",

author = "Vartak, {Ashish P.} and {Gabriela Deaciuc}, A. and Dwoskin, {Linda P.} and Crooks, {Peter A.}",

note = "Funding Information: The authors would like to thank the National Institutes of Health , NIDA Grant DA013519 for financial support. ",

year = "2010",

doi = "10.1016/j.bmcl.2010.04.117",

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pages = "3584--3587",

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T1 - Quinlobelane

T2 - A water-soluble lobelane analogue and inhibitor of VMAT2

AU - Vartak, Ashish P.

AU - Gabriela Deaciuc, A.

AU - Dwoskin, Linda P.

AU - Crooks, Peter A.

N1 - Funding Information: The authors would like to thank the National Institutes of Health , NIDA Grant DA013519 for financial support.

PY - 2010

Y1 - 2010

N2 - Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition.

AB - Replacing the phenyl groups in the structure of the VMAT2 inhibitor, lobelane with either pyridyl, quinolyl or indolyl groups affords novel analogues with improved water solubility. The synthetic methodologies reported herein also underscore the paucity of hydrogenation methods that offer selectivity in the synthesis of the different classes of heteroaromatic lobelane analogues. The quinolyl group was the only replacement for the phenyl group in lobelane that retained VMAT2 inhibition.

KW - Dopamine transport

KW - Lobeline analogs

KW - VMAT2

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 12

ER -

Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2

Abstract

Bibliographical note

Keywords

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