Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands

Jing Fang; Adwoa Akwabi-Ameyaw; Jonathan E. Britton; Subba R. Katamreddy; Frank Navas III; Aaron B. Miller; Shawn P. Williams; David W. Gray; Lisa A. Orband-Miller; Jean Shearin; Dennis Heyer

doi:10.1016/j.bmcl.2008.07.121

Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands

Jing Fang, Adwoa Akwabi-Ameyaw, Jonathan E. Britton, Subba R. Katamreddy, Frank Navas III, Aaron B. Miller, Shawn P. Williams, David W. Gray, Lisa A. Orband-Miller, Jean Shearin, Dennis Heyer

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

26 Citations (Scopus)

Abstract

A series of estrogen receptor ligands based on a 3-alkyl naphthalene scaffold was synthesized using an intramolecular enolate-alkyne cycloaromatization as the key step. Several of these compounds bearing a C6-OH group were shown to be high affinity ligands. All compounds had similar ERalpha and ERbeta binding affinity ranging from micromolar to low nanomolar.

Original language	English
Pages (from-to)	5075-5077
Number of pages	3
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	18
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2008.07.121
Publication status	Published - 15 Sept 2008

Keywords

Molecular Structure
Estrogen Receptor Modulators
Naphthalenes
Humans
Estrogen Receptor alpha
Combinatorial Chemistry Techniques
Selective Estrogen Receptor Modulators
Ligands
Female
Estrogen Receptor beta
Structure-Activity Relationship
Receptors, Estrogen

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10.1016/j.bmcl.2008.07.121

http://www.journals.elsevier.com/bioorganic-and-medicinal-chemistry-letters

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title = "Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands",

abstract = "A series of estrogen receptor ligands based on a 3-alkyl naphthalene scaffold was synthesized using an intramolecular enolate-alkyne cycloaromatization as the key step. Several of these compounds bearing a C6-OH group were shown to be high affinity ligands. All compounds had similar ERalpha and ERbeta binding affinity ranging from micromolar to low nanomolar.",

keywords = "Molecular Structure, Estrogen Receptor Modulators, Naphthalenes, Humans, Estrogen Receptor alpha, Combinatorial Chemistry Techniques, Selective Estrogen Receptor Modulators, Ligands, Female, Estrogen Receptor beta, Structure-Activity Relationship, Receptors, Estrogen",

author = "Jing Fang and Adwoa Akwabi-Ameyaw and Britton, {Jonathan E.} and Katamreddy, {Subba R.} and {Navas III}, Frank and Miller, {Aaron B.} and Williams, {Shawn P.} and Gray, {David W.} and Orband-Miller, {Lisa A.} and Jean Shearin and Dennis Heyer",

year = "2008",

month = sep,

day = "15",

doi = "10.1016/j.bmcl.2008.07.121",

language = "English",

volume = "18",

pages = "5075--5077",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "1464-3405",

publisher = "Elsevier",

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TY - JOUR

T1 - Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands

AU - Fang, Jing

AU - Akwabi-Ameyaw, Adwoa

AU - Britton, Jonathan E.

AU - Katamreddy, Subba R.

AU - Navas III, Frank

AU - Miller, Aaron B.

AU - Williams, Shawn P.

AU - Gray, David W.

AU - Orband-Miller, Lisa A.

AU - Shearin, Jean

AU - Heyer, Dennis

PY - 2008/9/15

Y1 - 2008/9/15

N2 - A series of estrogen receptor ligands based on a 3-alkyl naphthalene scaffold was synthesized using an intramolecular enolate-alkyne cycloaromatization as the key step. Several of these compounds bearing a C6-OH group were shown to be high affinity ligands. All compounds had similar ERalpha and ERbeta binding affinity ranging from micromolar to low nanomolar.

AB - A series of estrogen receptor ligands based on a 3-alkyl naphthalene scaffold was synthesized using an intramolecular enolate-alkyne cycloaromatization as the key step. Several of these compounds bearing a C6-OH group were shown to be high affinity ligands. All compounds had similar ERalpha and ERbeta binding affinity ranging from micromolar to low nanomolar.

KW - Molecular Structure

KW - Estrogen Receptor Modulators

KW - Naphthalenes

KW - Humans

KW - Estrogen Receptor alpha

KW - Combinatorial Chemistry Techniques

KW - Selective Estrogen Receptor Modulators

KW - Ligands

KW - Female

KW - Estrogen Receptor beta

KW - Structure-Activity Relationship

KW - Receptors, Estrogen

U2 - 10.1016/j.bmcl.2008.07.121

DO - 10.1016/j.bmcl.2008.07.121

M3 - Article

C2 - 18722117

SN - 1464-3405

VL - 18

SP - 5075

EP - 5077

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 18

ER -

Synthesis of 3-alkyl naphthalenes as novel estrogen receptor ligands

Abstract

Keywords

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