Synthesis of ketone analogues of prolyl and pipecolyl ester FKBP12 ligands

Yong Qian Wu; Douglas E. Wilkinson; David Limburg; Jia He Li; Hansjorg Sauer; Doug Ross; Shi Liang; Dawn Spicer; Heather Valentine; Mike Fuller; Hong Guo; Pam Howorth; Raj Soni; Yi Chen; Joseph P. Steiner; Gregory S. Hamilton

doi:10.1021/jm0200456

Synthesis of ketone analogues of prolyl and pipecolyl ester FKBP12 ligands

Yong Qian Wu, Douglas E. Wilkinson, David Limburg, Jia He Li, Hansjorg Sauer, Doug Ross, Shi Liang, Dawn Spicer, Heather Valentine, Mike Fuller, Hong Guo, Pam Howorth, Raj Soni, Yi Chen, Joseph P. Steiner, Gregory S. Hamilton

School of Medicine

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

12 Scopus citations

Abstract

The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

Original language	English (US)
Pages (from-to)	3558-3568
Number of pages	11
Journal	Journal of medicinal chemistry
Volume	45
Issue number	16
DOIs	https://doi.org/10.1021/jm0200456
State	Published - Aug 1 2002

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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title = "Synthesis of ketone analogues of prolyl and pipecolyl ester FKBP12 ligands",

abstract = "The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.",

author = "Wu, {Yong Qian} and Wilkinson, {Douglas E.} and David Limburg and Li, {Jia He} and Hansjorg Sauer and Doug Ross and Shi Liang and Dawn Spicer and Heather Valentine and Mike Fuller and Hong Guo and Pam Howorth and Raj Soni and Yi Chen and Steiner, {Joseph P.} and Hamilton, {Gregory S.}",

year = "2002",

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T1 - Synthesis of ketone analogues of prolyl and pipecolyl ester FKBP12 ligands

AU - Wu, Yong Qian

AU - Wilkinson, Douglas E.

AU - Limburg, David

AU - Li, Jia He

AU - Sauer, Hansjorg

AU - Ross, Doug

AU - Liang, Shi

AU - Spicer, Dawn

AU - Valentine, Heather

AU - Fuller, Mike

AU - Guo, Hong

AU - Howorth, Pam

AU - Soni, Raj

AU - Chen, Yi

AU - Steiner, Joseph P.

AU - Hamilton, Gregory S.

PY - 2002/8/1

Y1 - 2002/8/1

N2 - The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

AB - The recently discovered small-molecule ligands for the peptidyl and prolyl isomerases (PPIase) of FKBP12 have been shown to possess powerful neuroprotective and neuroregenerative effects. Ketone analogues of the prolyl and pipecolyl esters, which mimic only the FKBP binding domain portion of FK506, are proposed and an efficient synthetic strategy is presented in this report, along with the preliminary results of in vitro and in vivo biological studies.

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JO - Journal of medicinal chemistry

JF - Journal of medicinal chemistry

IS - 16

ER -

Synthesis of ketone analogues of prolyl and pipecolyl ester FKBP12 ligands

Abstract

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