Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template

Jihyae Ann; Wei Sun; Xing Zhou; Aeran Jung; Jisoo Baek; Sunho Lee; Changhoon Kim; Suyoung Yoon; Sunhye Hong; Sun Choi; Noe A. Turcios; Brienna K.A. Herold; Timothy E. Esch; Nancy E. Lewin; Adelle Abramovitz; Larry V. Pearce; Peter M. Blumberg; Jeewoo Lee

doi:10.1016/j.bmcl.2016.06.010

Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template

Jihyae Ann, Wei Sun, Xing Zhou, Aeran Jung, Jisoo Baek, Sunho Lee, Changhoon Kim, Suyoung Yoon, Sunhye Hong, Sun Choi, Noe A. Turcios, Brienna K.A. Herold, Timothy E. Esch, Nancy E. Lewin, Adelle Abramovitz, Larry V. Pearce, Peter M. Blumberg, Jeewoo Lee

Department of Pharmaceutical Sciences

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

11 Scopus citations

Abstract

A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S.

Original language	English
Pages (from-to)	3603-3607
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	26
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2016.06.010
State	Published - 2016

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd

Keywords

Analgesic
TRPV1 antagonists
Vanilloid receptor 1

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10.1016/j.bmcl.2016.06.010

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Ann, J., Sun, W., Zhou, X., Jung, A., Baek, J., Lee, S., Kim, C., Yoon, S., Hong, S., Choi, S., Turcios, N. A., Herold, B. K. A., Esch, T. E., Lewin, N. E., Abramovitz, A., Pearce, L. V., Blumberg, P. M., & Lee, J. (2016). Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template. Bioorganic and Medicinal Chemistry Letters, 26(15), 3603-3607. https://doi.org/10.1016/j.bmcl.2016.06.010

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title = "Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template",

abstract = "A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S.",

keywords = "Analgesic, TRPV1 antagonists, Vanilloid receptor 1",

author = "Jihyae Ann and Wei Sun and Xing Zhou and Aeran Jung and Jisoo Baek and Sunho Lee and Changhoon Kim and Suyoung Yoon and Sunhye Hong and Sun Choi and Turcios, \{Noe A.\} and Herold, \{Brienna K.A.\} and Esch, \{Timothy E.\} and Lewin, \{Nancy E.\} and Adelle Abramovitz and Pearce, \{Larry V.\} and Blumberg, \{Peter M.\} and Jeewoo Lee",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

year = "2016",

doi = "10.1016/j.bmcl.2016.06.010",

language = "English",

volume = "26",

pages = "3603--3607",

journal = "Bioorganic and Medicinal Chemistry Letters",

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Ann, J, Sun, W, Zhou, X, Jung, A, Baek, J, Lee, S, Kim, C, Yoon, S, Hong, S, Choi, S, Turcios, NA, Herold, BKA, Esch, TE, Lewin, NE, Abramovitz, A, Pearce, LV, Blumberg, PM & Lee, J 2016, 'Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template', Bioorganic and Medicinal Chemistry Letters, vol. 26, no. 15, pp. 3603-3607. https://doi.org/10.1016/j.bmcl.2016.06.010

TY - JOUR

T1 - Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template

AU - Ann, Jihyae

AU - Sun, Wei

AU - Zhou, Xing

AU - Jung, Aeran

AU - Baek, Jisoo

AU - Lee, Sunho

AU - Kim, Changhoon

AU - Yoon, Suyoung

AU - Hong, Sunhye

AU - Choi, Sun

AU - Turcios, Noe A.

AU - Herold, Brienna K.A.

AU - Esch, Timothy E.

AU - Lewin, Nancy E.

AU - Abramovitz, Adelle

AU - Pearce, Larry V.

AU - Blumberg, Peter M.

AU - Lee, Jeewoo

PY - 2016

Y1 - 2016

N2 - A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S.

AB - A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S.

KW - Analgesic

KW - TRPV1 antagonists

KW - Vanilloid receptor 1

UR - https://www.scopus.com/pages/publications/84978878151

U2 - 10.1016/j.bmcl.2016.06.010

DO - 10.1016/j.bmcl.2016.06.010

M3 - Article

C2 - 27317643

AN - SCOPUS:84978878151

SN - 0960-894X

VL - 26

SP - 3603

EP - 3607

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 15

ER -

Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template

Abstract

Bibliographical note

Keywords

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