CB2 selective sulfamoyl benzamides: Optimization of the amide functionality

Allan J. Goodman; Christopher W. Ajello; Karin Worm; Bertrand Le Bourdonnec; Markku A. Savolainen; Heather O'Hare; Joel A. Cassel; Gabriel J. Stabley; Robert N. DeHaven; Christopher J. LaBuda; Michael Koblish; Patrick J. Little; Bernice L. Brogdon; Steven A. Smith; Roland E. Dolle

doi:10.1016/j.bmcl.2008.11.091

CB₂ selective sulfamoyl benzamides: Optimization of the amide functionality

Allan J. Goodman, Christopher W. Ajello, Karin Worm, Bertrand Le Bourdonnec, Markku A. Savolainen, Heather O'Hare, Joel A. Cassel, Gabriel J. Stabley, Robert N. DeHaven, Christopher J. LaBuda, Michael Koblish, Patrick J. Little, Bernice L. Brogdon, Steven A. Smith, Roland E. Dolle

Center for Drug Discovery

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

21 Scopus citations

Abstract

Previous research within our laboratories identified sulfamoyl benzamides as novel cannabinoid receptor ligands. Optimization of the amide linkage led to the reverse amide 40. The compound exhibited robust antiallodynic activity in a rodent pain model when administered intraperitoneally. Efficacy after oral administration was observed only when ABT, a cytochrome P450 suicide inhibitor, was coadministered.

Original language	English
Pages (from-to)	309-313
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	2
DOIs	https://doi.org/10.1016/j.bmcl.2008.11.091
State	Published - Jan 15 2009

Keywords

Antiallodynia
CB1
CB2
Cannabinoid
Sulfamoyl benzamides

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10.1016/j.bmcl.2008.11.091

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Goodman, A. J., Ajello, C. W., Worm, K., Bourdonnec, B. L., Savolainen, M. A., O'Hare, H., Cassel, J. A., Stabley, G. J., DeHaven, R. N., LaBuda, C. J., Koblish, M., Little, P. J., Brogdon, B. L., Smith, S. A., & Dolle, R. E. (2009). CB₂ selective sulfamoyl benzamides: Optimization of the amide functionality. Bioorganic and Medicinal Chemistry Letters, 19(2), 309-313. https://doi.org/10.1016/j.bmcl.2008.11.091

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title = "CB2 selective sulfamoyl benzamides: Optimization of the amide functionality",

abstract = "Previous research within our laboratories identified sulfamoyl benzamides as novel cannabinoid receptor ligands. Optimization of the amide linkage led to the reverse amide 40. The compound exhibited robust antiallodynic activity in a rodent pain model when administered intraperitoneally. Efficacy after oral administration was observed only when ABT, a cytochrome P450 suicide inhibitor, was coadministered.",

keywords = "Antiallodynia, CB1, CB2, Cannabinoid, Sulfamoyl benzamides",

author = "Goodman, {Allan J.} and Ajello, {Christopher W.} and Karin Worm and Bourdonnec, {Bertrand Le} and Savolainen, {Markku A.} and Heather O'Hare and Cassel, {Joel A.} and Stabley, {Gabriel J.} and DeHaven, {Robert N.} and LaBuda, {Christopher J.} and Michael Koblish and Little, {Patrick J.} and Brogdon, {Bernice L.} and Smith, {Steven A.} and Dolle, {Roland E.}",

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doi = "10.1016/j.bmcl.2008.11.091",

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Goodman, AJ, Ajello, CW, Worm, K, Bourdonnec, BL, Savolainen, MA, O'Hare, H, Cassel, JA, Stabley, GJ, DeHaven, RN, LaBuda, CJ, Koblish, M, Little, PJ, Brogdon, BL, Smith, SA & Dolle, RE 2009, 'CB₂ selective sulfamoyl benzamides: Optimization of the amide functionality', Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 2, pp. 309-313. https://doi.org/10.1016/j.bmcl.2008.11.091

TY - JOUR

T1 - CB2 selective sulfamoyl benzamides

T2 - Optimization of the amide functionality

AU - Goodman, Allan J.

AU - Ajello, Christopher W.

AU - Worm, Karin

AU - Bourdonnec, Bertrand Le

AU - Savolainen, Markku A.

AU - O'Hare, Heather

AU - Cassel, Joel A.

AU - Stabley, Gabriel J.

AU - DeHaven, Robert N.

AU - LaBuda, Christopher J.

AU - Koblish, Michael

AU - Little, Patrick J.

AU - Brogdon, Bernice L.

AU - Smith, Steven A.

AU - Dolle, Roland E.

PY - 2009/1/15

Y1 - 2009/1/15

N2 - Previous research within our laboratories identified sulfamoyl benzamides as novel cannabinoid receptor ligands. Optimization of the amide linkage led to the reverse amide 40. The compound exhibited robust antiallodynic activity in a rodent pain model when administered intraperitoneally. Efficacy after oral administration was observed only when ABT, a cytochrome P450 suicide inhibitor, was coadministered.

AB - Previous research within our laboratories identified sulfamoyl benzamides as novel cannabinoid receptor ligands. Optimization of the amide linkage led to the reverse amide 40. The compound exhibited robust antiallodynic activity in a rodent pain model when administered intraperitoneally. Efficacy after oral administration was observed only when ABT, a cytochrome P450 suicide inhibitor, was coadministered.

KW - Antiallodynia

KW - CB1

KW - CB2

KW - Cannabinoid

KW - Sulfamoyl benzamides

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U2 - 10.1016/j.bmcl.2008.11.091

DO - 10.1016/j.bmcl.2008.11.091

M3 - Article

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AN - SCOPUS:57749115645

SN - 0960-894X

VL - 19

SP - 309

EP - 313

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 2

ER -

CB₂ selective sulfamoyl benzamides: Optimization of the amide functionality

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Keywords

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