The Synthesis of 2-(1-Indenyl)-phenol: A Potential Ligand For Metallocene Polymerization Catalysts; and, ω-Iodoalkyl(methyl) Malonate Esters: Synthesis and Application in Bioconjugate Chemistry

Author

Sara E. Bendler, Eastern Illinois University

Degree Name

Master of Science (MS)

Semester of Degree Completion

2003

Thesis Director

Robert W. Chesnut

Abstract

Chapter I:

Metallocene catalysis is an important division of polymerization chemistry. The design of appropriate ligands for metallocene catalysts has focused on stereochemical control and structural diversity. The synthesis of the potential ligand 2-(1-indenyl)-phenol has been developed. Indenyl phenol ligands offer advancements over cyclopentadienyl ligands because the steric and electronic properties of the catalyst could be tailored to suit individual polymerization reactions. 2-(1-Indenyl)-phenol was synthesized with an overall yield of 4% and characterized with ¹H NMR and ¹³C NMR.

Chapter II:

A large percentage of breast malignancies overexpress the nuclear estrogen receptor (ER) protein. Binding to nuclear receptors is a mechanism for concentrating ligands in cells, and this pathway can be expanded to ligand analogues provided the analogue is still recognized by the receptor. Estradiol is a high-affinity ligand for the estrogen receptor, and 7α monosubstituted estradiol derivatives have also been shown to be high-affinity ligands for ER. Therefore an estradiol derivative with a cytotoxic moiety incorporated into a 7α substituent could selectively concentrate in breast malignancies to cause cell death. A generation of linkage molecules designed to incorporate a cytotoxic moiety into 7α substitutents of estradiol has been developed. Since bidentate carboxylate ligands are known to form highly stable complexes with platinum, malonate groups were chosen as the common element in this family of linkage molecules. Alkylating malonate groups with diiodoalkanes afforded ω-iodoalkyl(methyl) malonate esters. One specific ester, diisoamyl-6-iodohexyl(methyl) malonate, was used to alkylate the 7α position of an estradiol derivative.

Recommended Citation

Bendler, Sara E., "The Synthesis of 2-(1-Indenyl)-phenol: A Potential Ligand For Metallocene Polymerization Catalysts; and, ω-Iodoalkyl(methyl) Malonate Esters: Synthesis and Application in Bioconjugate Chemistry" (2003). Masters Theses. 1423.
https://thekeep.eiu.edu/theses/1423