Part I: Design, synthesis, and studies of novel age-inhibitors and age-breakers; Part II: Novel synthetic methods for organofluorine compound

Author

Jatin Mehta

Abstract

"Novel small molecule inhibitors and breakers of advanced glycation end-products (AGEs) have been synthesized and their in vitro inhibitory activities have been studied by ¹³C NMR, fluorescence, and UV-visible spectroscopy. We have demonstrated that these AGE-inhibitors and AGE-breakers were found to be more effective in their sequestration of AGE intermediates, such as dehydroascorbate (DHA) than the state-of-the art phenacylthiazolium bromide (PTB)-based AGE-inhibitors and AGE-breakers. Citric acid and other polyphenolic antioxidants have substantial AGE inhibitory effects in the D-glucose/leucine or benzylamine Maillard reaction model systems, and thus they are suitable as dietary additives for ameliorating AGE-induced complications.

Organofluorine compounds have found numerous applications as pharmaceutically interesting compounds, and toward developing novel synthetic methods for organofluorine compounds, we have investigated synthetic strategies for gem-difluoro and trifluormethyl compounds. gem-Difluorination of 1,3-dithiolanes, obtained from the corresponding ketones, form gem-difluoromethylene compounds through the photoredox catalysis, using photocatalyst 9-fluorenone in the presence of visible light (household bulb 13W CFL). This reaction proceeds under mild conditions and is applicable to gem-difluorination of variously substituted diaryl 1,3-dithiolanes. We have also developed a novel NHC-catalyzed trifluoromethylation of aromatic N-tosyl aldimines with electron-withdrawing as well as electron-donating groups on the aryl ring. We have synthesized a series of novel purine-based triazole derivatives as potential CDK-inhibitors and characterized their structures using high-field ¹H- and ¹³C-NMR spectroscopy”--Abstract, page iii.

Advisor(s)

Reddy, Prakash

Committee Member(s)

Ercal, Nuran
Ma, Yinfa
Winiarz, Jeffrey G.
Chandrashekhara, K.

Department(s)

Chemistry

Degree Name

Ph. D. in Chemistry

Publisher

Missouri University of Science and Technology

Publication Date

Fall 2018

Pagination

xx, 177 pages

Note about bibliography

Includes bibliographic references (pages 153-176).

Rights

© 2018 Jatin Mehta, All rights reserved.

Document Type

Dissertation - Open Access

File Type

text

Language

English

Thesis Number

T 12089

Recommended Citation

Mehta, Jatin, "Part I: Design, synthesis, and studies of novel age-inhibitors and age-breakers; Part II: Novel synthetic methods for organofluorine compound" (2018). Doctoral Dissertations. 3136.
https://scholarsmine.mst.edu/doctoral_dissertations/3136