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Design and Synthesis of Chiral Dihydrodioxins, 2,2,3-triaryl- and 2,3-diaryl-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins; As Photochemical DNA Cleaving Agents

Coyle, William Joseph
http://rave.ohiolink.edu/etdc/view?acc_num=ucin998313007

Abstract Details

2001, PhD, University of Cincinnati, Arts and Sciences : Chemistry.
A series of Dihydrodioxins has been synthesized as part of a research program investigating the development of 2,2,3-triaryl- and 2,3-diaryl-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins (dihydrodioxins) as efficient DNA cleaving agents. The dihydrodioxins are unique, photochemical, masked o-quinone DNA cleaving agents. When used in combination with DNA sequence-recognizing groups, they have the potential to be an important tool in the fight against cancer, and /or genetic disease. The focus of this research was the synthesis of chiral dihydrodioxins, utilizing the Schönberg-Mustafa reaction, a 2+4 photocyclization of phenanthroquinone (PAQ) and an appropriate alkene. The products of this reaction involving a variety of different alkenes is reported, and their use, and / or potential use, as chiral DNA cleaving agents is evaluated. The chiral resolution of a selected 2,3-diaryl-dihydrodioxin, followed by an examination of the DNA cleaving potential of the enantiomers is reported.
R. Wilson (Advisor)
Chemistry, Organic
DNA CLEAVING AGENT; CHIRAL; ORGANIC CHEMISTRY

Recommended Citations

Citations

  • Coyle, W. J. (2001). Design and Synthesis of Chiral Dihydrodioxins, 2,2,3-triaryl- and 2,3-diaryl-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins; As Photochemical DNA Cleaving Agents [Doctoral dissertation, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin998313007

    APA Style (7th edition)

  • Coyle, William. Design and Synthesis of Chiral Dihydrodioxins, 2,2,3-triaryl- and 2,3-diaryl-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins; As Photochemical DNA Cleaving Agents. 2001. University of Cincinnati, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin998313007.

    MLA Style (8th edition)

  • Coyle, William. "Design and Synthesis of Chiral Dihydrodioxins, 2,2,3-triaryl- and 2,3-diaryl-2,3-dihydrophenanthro[9,10-b]-1,4-dioxins; As Photochemical DNA Cleaving Agents." Doctoral dissertation, University of Cincinnati, 2001. http://rave.ohiolink.edu/etdc/view?acc_num=ucin998313007

    Chicago Manual of Style (17th edition)

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© 2001, all rights reserved.
This open access ETD is published by University of Cincinnati and OhioLINK.
Release 3.2.12