DESIGN AND SYNTHESIS OF PURINE BASED NEUROPROTECTORS AND NOVEL SYNTHETIC METHODS FOR THE TRIFLUOROMETHYLATION OF ALDEHYDE HYDRAZONES

Author

Puspa Aryal, Missouri University of Science and Technology

Keywords and Phrases

Organic Synthesis

Abstract

"Purine-derived compounds are widely investigated as cyclin-dependent kinase inhibitors that have broad applications in the design of pharmaceuticals for treating diseases, such as diabetes, atherosclerosis, and cancers. Towards the goal of effective AGE-inhibitors, and neuroprotector compounds we have synthesized a series of novel purine-based triazoles and investigated their neuroprotective effects, using SHSY-3Y human neuroblastoma cell line. Through these studies, we have identified purine-based neuroprotector compounds that favorably modulate oxidative stress induced by the Fenton reaction-generated reactive oxygen species (ROS).

The C(sp²−H)-trifluoromethylation of hydrazones would give access to the αtrifluoromethylated hydrazones that can serve as intermediates in the synthesis of pharmaceutically interesting, fluorinated compounds. Herein, we demonstrate two different synthetic routes for the C(sp²−H)-trifluoromethylation of the aldehyde hydrazones using the readily available and cost-effective Langlois reagent (sodium trifluoromethanesulfinate). This reaction scheme is broadly applicable to a series of aromatic aldehyde N-amino morpholine hydrazones to give the corresponding C(sp²)- trifluoromethyl hydrazones in moderate to high yields. Cu (II)-catalysis provides a cost-effective synthetic approach while Rose Bengal mediated photo redox catalyzed method provides environmentally benign synthetic method for the trifluoromethylation of aldehyde hydrazones"--Abstract, p. iii

Advisor(s)

Reddy, Prakash

Committee Member(s)

Winiarz, Jeffrey G.
Choudhury, Amitava
Nam, Paul Ki-Souk
Chandrashekhara, K.

Department(s)

Chemistry

Degree Name

Ph. D. in Chemistry

Publisher

Missouri University of Science and Technology

Publication Date

Fall 2022

Pagination

ix, 113 pages

Note about bibliography

Includes_bibliographical_references_(pages 107-112)

Rights

© 2022 Puspa Aryal, All Rights Reserved

Document Type

Dissertation - Open Access

File Type

text

Language

English

Thesis Number

T 12186

Recommended Citation

Aryal, Puspa, "DESIGN AND SYNTHESIS OF PURINE BASED NEUROPROTECTORS AND NOVEL SYNTHETIC METHODS FOR THE TRIFLUOROMETHYLATION OF ALDEHYDE HYDRAZONES" (2022). Doctoral Dissertations. 3234.
https://scholarsmine.mst.edu/doctoral_dissertations/3234