Synthesis and SAR of tolylamine 5-HT6 antagonists

Jamie M. Singer; Michael W. Wilson; Paul D. Johnson; Shelley R. Graham; Leonard W. Cooke; Robin L. Roof; Peter A. Boxer; Lisa H. Gold; Leonard T. Meltzer; Ann Janssen; Nicole Roush; Jeffrey E. Campbell; Ti Zhi Su; Susan I. Hurst; Chad L. Stoner; Jacob B. Schwarz

doi:10.1016/j.bmcl.2009.03.077

Synthesis and SAR of tolylamine 5-HT₆ antagonists

Jamie M. Singer, Michael W. Wilson, Paul D. Johnson, Shelley R. Graham, Leonard W. Cooke, Robin L. Roof, Peter A. Boxer, Lisa H. Gold, Leonard T. Meltzer, Ann Janssen, Nicole Roush, Jeffrey E. Campbell, Ti Zhi Su, Susan I. Hurst, Chad L. Stoner, Jacob B. Schwarz

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

21 Scopus citations

Abstract

The synthesis and SAR of tolylamines with 5-HT₆ receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT₆ examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm.

Original language	English
Pages (from-to)	2409-2412
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	19
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2009.03.077
State	Published - May 1 2009
Externally published	Yes

Keywords

5-HT6
Object recognition
Phenylpiperidine

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10.1016/j.bmcl.2009.03.077

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Singer, J. M., Wilson, M. W., Johnson, P. D., Graham, S. R., Cooke, L. W., Roof, R. L., Boxer, P. A., Gold, L. H., Meltzer, L. T., Janssen, A., Roush, N., Campbell, J. E., Su, T. Z., Hurst, S. I., Stoner, C. L., & Schwarz, J. B. (2009). Synthesis and SAR of tolylamine 5-HT₆ antagonists. Bioorganic and Medicinal Chemistry Letters, 19(9), 2409-2412. https://doi.org/10.1016/j.bmcl.2009.03.077

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abstract = "The synthesis and SAR of tolylamines with 5-HT6 receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT6 examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm.",

keywords = "5-HT6, Object recognition, Phenylpiperidine",

author = "Singer, {Jamie M.} and Wilson, {Michael W.} and Johnson, {Paul D.} and Graham, {Shelley R.} and Cooke, {Leonard W.} and Roof, {Robin L.} and Boxer, {Peter A.} and Gold, {Lisa H.} and Meltzer, {Leonard T.} and Ann Janssen and Nicole Roush and Campbell, {Jeffrey E.} and Su, {Ti Zhi} and Hurst, {Susan I.} and Stoner, {Chad L.} and Schwarz, {Jacob B.}",

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doi = "10.1016/j.bmcl.2009.03.077",

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AU - Singer, Jamie M.

AU - Wilson, Michael W.

AU - Johnson, Paul D.

AU - Graham, Shelley R.

AU - Cooke, Leonard W.

AU - Roof, Robin L.

AU - Boxer, Peter A.

AU - Gold, Lisa H.

AU - Meltzer, Leonard T.

AU - Janssen, Ann

AU - Roush, Nicole

AU - Campbell, Jeffrey E.

AU - Su, Ti Zhi

AU - Hurst, Susan I.

AU - Stoner, Chad L.

AU - Schwarz, Jacob B.

PY - 2009/5/1

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N2 - The synthesis and SAR of tolylamines with 5-HT6 receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT6 examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm.

AB - The synthesis and SAR of tolylamines with 5-HT6 receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT6 examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm.

KW - 5-HT6

KW - Object recognition

KW - Phenylpiperidine

UR - http://www.scopus.com/inward/record.url?scp=64249172204&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2009.03.077

DO - 10.1016/j.bmcl.2009.03.077

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AN - SCOPUS:64249172204

SN - 0960-894X

VL - 19

SP - 2409

EP - 2412

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 9

ER -

Synthesis and SAR of tolylamine 5-HT₆ antagonists

Abstract

Keywords

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