Synthesis & Evaluation Of Thiophene Derivatives As CXCR4 Antagonists

Author

Francisco Javier Garcia Jr., Georgia State UniversityFollow

Date of Award

5-3-2017

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Dr. Suazette Reid Mooring

Second Advisor

Dr. Donald Hamelberg

Third Advisor

Dr. Jeremiah Harden

Abstract

There is a lack of good CXCR4 inhibitors that treat cancer cell metastasis and autoimmune diseases without serious drawbacks. AMD3100 and WZ811 are the CXCR4 antagonists that were the initial structural basis for our new potential therapeutics. Molecular modeling and the principles of drug discovery and design were used to plan the synthesis of the compounds presented here. These compounds were synthesized via reductive amination, and then purified via flash column chromatography or preparatory thin layer chromatography. The small molecules were then characterized via melting point, high resolution MS, ¹³C, and ¹H NMR spectroscopy. The Matrigel invasion assay and binding affinity assay were used to screen the potency of the compounds. Compounds that showed high potency in these assays were then subjected to the carrageenan mouse paw edema test. Two lead compounds have emerged as candidates for further testing (2v, and 2a).

DOI

https://doi.org/10.57709/10101786

Recommended Citation

Garcia, Francisco Javier Jr., "Synthesis & Evaluation Of Thiophene Derivatives As CXCR4 Antagonists." Thesis, Georgia State University, 2017.
doi: https://doi.org/10.57709/10101786