Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers

Marion A Franks; Edward A. Schrader; E. Christine Pietsch; Daniel R. Pennella; Suzy V. Torti; Mark E. Welker

doi:10.1016/j.bmc.2004.12.037

Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers

Marion A Franks
, Edward A. Schrader
, E. Christine Pietsch
, Daniel R. Pennella
, Suzy V. Torti
, Mark E. Welker

Chemistry

Wake Forest University
Wake Forest University School of Medicine

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

19 Scopus citations

Abstract

A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2221-2233
Number of pages	13
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	6
DOIs	https://doi.org/10.1016/j.bmc.2004.12.037
State	Published - Mar 15 2005

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Cancer chemoprevention
NQO1
Sulfur heterocycle synthesis

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10.1016/j.bmc.2004.12.037

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Franks, M. A., Schrader, E. A., Pietsch, E. C., Pennella, D. R., Torti, S. V., & Welker, M. E. (2005). Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers. Bioorganic and Medicinal Chemistry, 13(6), 2221-2233. https://doi.org/10.1016/j.bmc.2004.12.037

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abstract = "A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers. {\textcopyright} 2004 Elsevier Ltd. All rights reserved.",

keywords = "Cancer chemoprevention, NQO1, Sulfur heterocycle synthesis",

author = "Franks, \{Marion A\} and Schrader, \{Edward A.\} and Pietsch, \{E. Christine\} and Pennella, \{Daniel R.\} and Torti, \{Suzy V.\} and Welker, \{Mark E.\}",

year = "2005",

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doi = "10.1016/j.bmc.2004.12.037",

language = "English",

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Franks, MA, Schrader, EA, Pietsch, EC, Pennella, DR, Torti, SV & Welker, ME 2005, 'Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers', Bioorganic and Medicinal Chemistry, vol. 13, no. 6, pp. 2221-2233. https://doi.org/10.1016/j.bmc.2004.12.037

Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers. / Franks, Marion A; Schrader, Edward A.; Pietsch, E. Christine et al.
In: Bioorganic and Medicinal Chemistry, Vol. 13, No. 6, 15.03.2005, p. 2221-2233.

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

TY - JOUR

T1 - Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers

AU - Franks, Marion A

AU - Schrader, Edward A.

AU - Pietsch, E. Christine

AU - Pennella, Daniel R.

AU - Torti, Suzy V.

AU - Welker, Mark E.

PY - 2005/3/15

Y1 - 2005/3/15

N2 - A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers. © 2004 Elsevier Ltd. All rights reserved.

AB - A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers. © 2004 Elsevier Ltd. All rights reserved.

KW - Cancer chemoprevention

KW - NQO1

KW - Sulfur heterocycle synthesis

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JO - Bioorganic and Medicinal Chemistry

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Franks MA, Schrader EA, Pietsch EC, Pennella DR, Torti SV, Welker ME. Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers. Bioorganic and Medicinal Chemistry. 2005 Mar 15;13(6):2221-2233. doi: 10.1016/j.bmc.2004.12.037

Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers

Abstract

UN SDGs

Keywords

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