Synthesis and radiosynthesis of 17α -[p-(iodophenylethynyl)]estra-3,17β-diols

Jian Wang; Masataka Watanabe; Shuntaro Mataka; Thies Thiemann; Goreti Ribeiro Morais; Fernanda Roleira; Elisiario Tavares Da Silva; Cristina Melo E Silva

doi:10.1515/znb-2003-0813

Synthesis and radiosynthesis of 17α -[p-(iodophenylethynyl)]estra-3,17β-diols

Jian Wang
, Masataka Watanabe
, Shuntaro Mataka
, Thies Thiemann
, Goreti Ribeiro Morais
, Fernanda Roleira
, Elisiario Tavares Da Silva
, Cristina Melo E Silva

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

6 Citations (Scopus)

Abstract

Estrones have been subjected to an addition reaction with [(4-ethynylphenyl)azo]pyrrolidine to provide 17 α -{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-3,17 β-diols. A subsequent iodination with iodotrimethylsilane, produced in situ from chlorotrimethylsilane and NaI, leads to 17α -(p-iodophenylethynyl)estra-3,17 β-diols. This reaction can also be carried out with Na¹²⁵I to give radiolabelled estra-3,17 β-diols, which are potentially useful radiodiagnostic agents for the detection of estrogen positive breast cancer. The stability of the radiolabelled compounds is exemplified in a stability study of 3-O-methyl 17 α-(p-[¹²⁵I]iodophenylethynyl)estra-1,3,5(10),6-tetraene-17 β-ol in acetonitrile.

Original language	English
Pages (from-to)	799-804
Number of pages	6
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	58
Issue number	8
DOIs	https://doi.org/10.1515/znb-2003-0813
Publication status	Published - Aug 1 2003
Externally published	Yes

Keywords

Radioiodination
Steroids
Triazenes

ASJC Scopus subject areas

General Chemistry

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@article{76fc83935dcf4f44933ab60c33ce095a,

title = "Synthesis and radiosynthesis of 17α -[p-(iodophenylethynyl)]estra-3,17β-diols",

abstract = "Estrones have been subjected to an addition reaction with [(4-ethynylphenyl)azo]pyrrolidine to provide 17 α -\{4-[(pyrrolidin-1-yl)-azo]phenylethynyl\}estra-3,17 β-diols. A subsequent iodination with iodotrimethylsilane, produced in situ from chlorotrimethylsilane and NaI, leads to 17α -(p-iodophenylethynyl)estra-3,17 β-diols. This reaction can also be carried out with Na125I to give radiolabelled estra-3,17 β-diols, which are potentially useful radiodiagnostic agents for the detection of estrogen positive breast cancer. The stability of the radiolabelled compounds is exemplified in a stability study of 3-O-methyl 17 α-(p-[125I]iodophenylethynyl)estra-1,3,5(10),6-tetraene-17 β-ol in acetonitrile.",

keywords = "Radioiodination, Steroids, Triazenes",

author = "Jian Wang and Masataka Watanabe and Shuntaro Mataka and Thies Thiemann and \{Ribeiro Morais\}, Goreti and Fernanda Roleira and \{Da Silva\}, \{Elisiario Tavares\} and \{Melo E Silva\}, Cristina",

year = "2003",

month = aug,

day = "1",

doi = "10.1515/znb-2003-0813",

language = "English",

volume = "58",

pages = "799--804",

journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",

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TY - JOUR

T1 - Synthesis and radiosynthesis of 17α -[p-(iodophenylethynyl)]estra-3,17β-diols

AU - Wang, Jian

AU - Watanabe, Masataka

AU - Mataka, Shuntaro

AU - Thiemann, Thies

AU - Ribeiro Morais, Goreti

AU - Roleira, Fernanda

AU - Da Silva, Elisiario Tavares

AU - Melo E Silva, Cristina

PY - 2003/8/1

Y1 - 2003/8/1

N2 - Estrones have been subjected to an addition reaction with [(4-ethynylphenyl)azo]pyrrolidine to provide 17 α -{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-3,17 β-diols. A subsequent iodination with iodotrimethylsilane, produced in situ from chlorotrimethylsilane and NaI, leads to 17α -(p-iodophenylethynyl)estra-3,17 β-diols. This reaction can also be carried out with Na125I to give radiolabelled estra-3,17 β-diols, which are potentially useful radiodiagnostic agents for the detection of estrogen positive breast cancer. The stability of the radiolabelled compounds is exemplified in a stability study of 3-O-methyl 17 α-(p-[125I]iodophenylethynyl)estra-1,3,5(10),6-tetraene-17 β-ol in acetonitrile.

AB - Estrones have been subjected to an addition reaction with [(4-ethynylphenyl)azo]pyrrolidine to provide 17 α -{4-[(pyrrolidin-1-yl)-azo]phenylethynyl}estra-3,17 β-diols. A subsequent iodination with iodotrimethylsilane, produced in situ from chlorotrimethylsilane and NaI, leads to 17α -(p-iodophenylethynyl)estra-3,17 β-diols. This reaction can also be carried out with Na125I to give radiolabelled estra-3,17 β-diols, which are potentially useful radiodiagnostic agents for the detection of estrogen positive breast cancer. The stability of the radiolabelled compounds is exemplified in a stability study of 3-O-methyl 17 α-(p-[125I]iodophenylethynyl)estra-1,3,5(10),6-tetraene-17 β-ol in acetonitrile.

KW - Radioiodination

KW - Steroids

KW - Triazenes

UR - https://www.scopus.com/pages/publications/0141729378

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DO - 10.1515/znb-2003-0813

M3 - Article

AN - SCOPUS:0141729378

SN - 0932-0776

VL - 58

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EP - 804

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

IS - 8

ER -

Synthesis and radiosynthesis of 17α -[p-(iodophenylethynyl)]estra-3,17β-diols

Abstract

Keywords

ASJC Scopus subject areas

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