Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents

Ling Wei Hsin; Thomas Prisinzano; Chavon R. Wilkerson; Christina M. Dersch; Robert Horel; Arthur E. Jacobson; Richard B. Rothman; Kenner C. Rice

doi:10.1016/S0960-894X(02)00940-X

Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents

Ling Wei Hsin
, Thomas Prisinzano
, Chavon R. Wilkerson
, Christina M. Dersch
, Robert Horel
, Arthur E. Jacobson
, Richard B. Rothman
, Kenner C. Rice

Producción científica: Article › revisión exhaustiva

16 Citas (Scopus)

Resumen

A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over the serotonin transporter (SERT) than the corresponding R enantiomers. Compound (+)-11 showed high affinity and selectivity for DAT over the SERT and, therefore, is a potential candidate for the development of a long-acting cocaine abuse therapeutic agent.

Idioma original	English
Páginas (desde-hasta)	553-556
Número de páginas	4
Publicación	Bioorganic and Medicinal Chemistry Letters
Volumen	13
N.º	3
DOI	https://doi.org/10.1016/S0960-894X(02)00940-X
Estado	Published - feb 2003

Nota bibliográfica

Funding Information:
The authors (L.M.C., N.I.D.D.K.) thank the National Institute on Drug Abuse, NIH, for partial financial support of our research program. The authors also thank Noel Whitaker and Wesley White (N.I.D.D.K., N.I.H.) for mass spectral analysis.

Financiación

The authors (L.M.C., N.I.D.D.K.) thank the National Institute on Drug Abuse, NIH, for partial financial support of our research program. The authors also thank Noel Whitaker and Wesley White (N.I.D.D.K., N.I.H.) for mass spectral analysis.

Financiadores	Número del financiador
National Institutes of Health (NIH)
National Institute on Drug Abuse
National Institute of Diabetes and Digestive and Kidney Diseases	Z01DK059501

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0960-894X(02)00940-X

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Hsin, L. W., Prisinzano, T., Wilkerson, C. R., Dersch, C. M., Horel, R., Jacobson, A. E., Rothman, R. B., & Rice, K. C. (2003). Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents. Bioorganic and Medicinal Chemistry Letters, 13(3), 553-556. https://doi.org/10.1016/S0960-894X(02)00940-X

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title = "Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents",

abstract = "A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over the serotonin transporter (SERT) than the corresponding R enantiomers. Compound (+)-11 showed high affinity and selectivity for DAT over the SERT and, therefore, is a potential candidate for the development of a long-acting cocaine abuse therapeutic agent.",

author = "Hsin, \{Ling Wei\} and Thomas Prisinzano and Wilkerson, \{Chavon R.\} and Dersch, \{Christina M.\} and Robert Horel and Jacobson, \{Arthur E.\} and Rothman, \{Richard B.\} and Rice, \{Kenner C.\}",

note = "Funding Information: The authors (L.M.C., N.I.D.D.K.) thank the National Institute on Drug Abuse, NIH, for partial financial support of our research program. The authors also thank Noel Whitaker and Wesley White (N.I.D.D.K., N.I.H.) for mass spectral analysis.",

year = "2003",

month = feb,

doi = "10.1016/S0960-894X(02)00940-X",

language = "English",

volume = "13",

pages = "553--556",

number = "3",

}

Hsin, LW, Prisinzano, T, Wilkerson, CR, Dersch, CM, Horel, R, Jacobson, AE, Rothman, RB & Rice, KC 2003, 'Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents', Bioorganic and Medicinal Chemistry Letters, vol. 13, n.º 3, pp. 553-556. https://doi.org/10.1016/S0960-894X(02)00940-X

Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents. / Hsin, Ling Wei; Prisinzano, Thomas; Wilkerson, Chavon R. et al.
En: Bioorganic and Medicinal Chemistry Letters, Vol. 13, N.º 3, 02.2003, p. 553-556.

Producción científica: Article › revisión exhaustiva

TY - JOUR

T1 - Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents

AU - Hsin, Ling Wei

AU - Prisinzano, Thomas

AU - Wilkerson, Chavon R.

AU - Dersch, Christina M.

AU - Horel, Robert

AU - Jacobson, Arthur E.

AU - Rothman, Richard B.

AU - Rice, Kenner C.

N1 - Funding Information: The authors (L.M.C., N.I.D.D.K.) thank the National Institute on Drug Abuse, NIH, for partial financial support of our research program. The authors also thank Noel Whitaker and Wesley White (N.I.D.D.K., N.I.H.) for mass spectral analysis.

PY - 2003/2

Y1 - 2003/2

N2 - A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over the serotonin transporter (SERT) than the corresponding R enantiomers. Compound (+)-11 showed high affinity and selectivity for DAT over the SERT and, therefore, is a potential candidate for the development of a long-acting cocaine abuse therapeutic agent.

AB - A series of optically pure phenyl-and non-phenyl-substituted 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines was synthesized and their binding affinity for dopamine transporter (DAT) was investigated. The analogues with a hydroxyl group in the S configuration were more selective for the DAT over the serotonin transporter (SERT) than the corresponding R enantiomers. Compound (+)-11 showed high affinity and selectivity for DAT over the SERT and, therefore, is a potential candidate for the development of a long-acting cocaine abuse therapeutic agent.

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VL - 13

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 3

ER -

Synthesis and dopamine transporter affinity of chiral 1-[2-[bis(4-fluorophenyl)methoxy]ethyl]-4-(2-hydroxypropyl)piperazines as potential cocaine abuse therapeutic agents

Resumen

Nota bibliográfica

Financiación

ASJC Scopus subject areas

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