Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain

Lucas C. Kopel; Mahmoud S. Ahmed; Fathi T. Halaweish

doi:10.1016/j.steroids.2013.07.005

Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain

Lucas C. Kopel, Mahmoud S. Ahmed, Fathi T. Halaweish

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

16 Scopus citations

Abstract

Functionalized estrogen analogs have received interest due to their unique and differing biological activity compared to their parent compounds. The synthesis of a new class of 3-methoxyestrone analogs functionalized at the C17 position possessing both alkyl and aryl substituted α,β-unsaturated ketones is described, along with their thiophenol conjugate addition products.

Original language	English (US)
Pages (from-to)	1119-1125
Number of pages	7
Journal	Steroids
Volume	78
Issue number	11
DOIs	https://doi.org/10.1016/j.steroids.2013.07.005
State	Published - 2013
Externally published	Yes

Keywords

Aldol
Enone
Estrone
Sulfa-Michael addition
Thiol

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Endocrinology
Pharmacology
Clinical Biochemistry
Organic Chemistry

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10.1016/j.steroids.2013.07.005

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title = "Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain",

abstract = "Functionalized estrogen analogs have received interest due to their unique and differing biological activity compared to their parent compounds. The synthesis of a new class of 3-methoxyestrone analogs functionalized at the C17 position possessing both alkyl and aryl substituted α,β-unsaturated ketones is described, along with their thiophenol conjugate addition products.",

keywords = "Aldol, Enone, Estrone, Sulfa-Michael addition, Thiol",

author = "Kopel, {Lucas C.} and Ahmed, {Mahmoud S.} and Halaweish, {Fathi T.}",

note = "Funding Information: We wish to acknowledge the South Dakota Board of Regents-2010 BCAAP (Biological Control and Analysis by Applied Photonics) Center for financial support. We are also grateful to Dr. Andrew Sykes and Vinothini Balasubramanian (University of South Dakota) for their help in determining the X-ray structure of the OTMS cyanohydrin product 8 and Dr. Alice Bergmann (University of Buffalo) for performing the high-resolution mass spectrometry. ",

year = "2013",

doi = "10.1016/j.steroids.2013.07.005",

language = "English (US)",

volume = "78",

pages = "1119--1125",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Inc.",

number = "11",

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TY - JOUR

T1 - Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain

AU - Kopel, Lucas C.

AU - Ahmed, Mahmoud S.

AU - Halaweish, Fathi T.

N1 - Funding Information: We wish to acknowledge the South Dakota Board of Regents-2010 BCAAP (Biological Control and Analysis by Applied Photonics) Center for financial support. We are also grateful to Dr. Andrew Sykes and Vinothini Balasubramanian (University of South Dakota) for their help in determining the X-ray structure of the OTMS cyanohydrin product 8 and Dr. Alice Bergmann (University of Buffalo) for performing the high-resolution mass spectrometry.

PY - 2013

Y1 - 2013

N2 - Functionalized estrogen analogs have received interest due to their unique and differing biological activity compared to their parent compounds. The synthesis of a new class of 3-methoxyestrone analogs functionalized at the C17 position possessing both alkyl and aryl substituted α,β-unsaturated ketones is described, along with their thiophenol conjugate addition products.

AB - Functionalized estrogen analogs have received interest due to their unique and differing biological activity compared to their parent compounds. The synthesis of a new class of 3-methoxyestrone analogs functionalized at the C17 position possessing both alkyl and aryl substituted α,β-unsaturated ketones is described, along with their thiophenol conjugate addition products.

KW - Aldol

KW - Enone

KW - Estrone

KW - Sulfa-Michael addition

KW - Thiol

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DO - 10.1016/j.steroids.2013.07.005

M3 - Article

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AN - SCOPUS:84882778899

SN - 0039-128X

VL - 78

SP - 1119

EP - 1125

JO - Steroids

JF - Steroids

IS - 11

ER -

Synthesis of novel estrone analogs by incorporation of thiophenols via conjugate addition to an enone side chain

Abstract

Keywords

ASJC Scopus subject areas

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