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Synthesis and Characterization of Oxazaphospholidinone Phosphorus Mustard Derivatives

Harper, Marc Alan
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1596552579697146

Abstract Details

2020, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
This research describes the synthesis and characterization of oxazaphospholidinone phosphorus mustard derivatives (OAP). These products are analogous to the FDA approved chemotherapeutic drug, cyclophosphamide. It is known that the nitrogen mustard moiety of cyclophosphamide forms cross-linkages with DNA strands, thus inhibiting the replication of cells. This has proven to be a successful method of slowing the rapid replication of cancerous cells. Through the reaction of various commercially available chiral amino alcohols and bis-(2-chloroethyl)-phosphoramidic dichloride, diastereomeric mixtures were observed. The mixtures were purified via flash column chromatography furnishing moderate overall yields (46 – 77%). The compounds were distinguished through 31P NMR shifts and were hypothesized to correspond to a specific configuration where the amino alcohol substituent is opposite (anti) or on the same side (syn) of the nitrogen mustard moiety. In the anti-configuration, the molecule produces a more upfield shift and in the syn-configuration, a more downfield shift. Determination of the absolute configuration with respect to phosphorus was carried out using single crystal X-ray diffraction (SC-XRD). Mass spectrometry was also used to determine if the diastereomers produce distinct fragmentation patterns.
John Jackson , PhD (Advisor)
Peter Norris , PhD (Committee Member)
Douglas Genna , PhD (Committee Member)
158 p.
Organic Chemistry
Oxazaphospholidinones; Cyclophosphamide; Nitrogen Mustard; Alkylating Agents

Recommended Citations

Citations

  • Harper, M. A. (2020). Synthesis and Characterization of Oxazaphospholidinone Phosphorus Mustard Derivatives [Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1596552579697146

    APA Style (7th edition)

  • Harper, Marc. Synthesis and Characterization of Oxazaphospholidinone Phosphorus Mustard Derivatives . 2020. Youngstown State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1596552579697146.

    MLA Style (8th edition)

  • Harper, Marc. "Synthesis and Characterization of Oxazaphospholidinone Phosphorus Mustard Derivatives ." Master's thesis, Youngstown State University, 2020. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1596552579697146

    Chicago Manual of Style (17th edition)

ysu1596552579697146
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This open access ETD is published by Youngstown State University and OhioLINK.
Release 3.2.12