Date of Award

12-2020

Degree Type

Dissertation

Degree Name

Ph.D.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Mark L. Trudell

Second Advisor

Branko S. Jursic

Third Advisor

Viktor Poltavets

Fourth Advisor

Phoebe Anne Zito

Abstract

Acetaminophen is a well-known analgesic that can manage pain and reduce fever. SCP-1 is a derivative of acetaminophen that showed significantly reduced hepatotoxicity and nephrotoxicity comparative to acetaminophen. Nitric oxides have been well known to play a key role in a wide variety of physiological and pathophysiological important processes. It was therefore of interest to synthesize a nitric oxide donor linked to SCP-1 that could have enhanced analgesic and antipyretic activity. A furoxan CAS 1609 as NO-donor was synthesized and linked to SCP-1 successfully. The furoxan CAS 1609 was initially synthesized from tetronic acid to give 1,2- dioxime in 86 % yield. The furoxan 4-hydroxymethyl carboxymethyl ester was obtained in 55 % yield by using t-butyl hypochlorite as an oxidation agent. The furoxan 4-hydroxymethyl carboxymethyl ester was treated with ammonia solution in methanol and converted the ester group into an amide moiety and furnish the targeted furoxan CAS 1609 in 98% yield. The CAS 1609 was coupled with SCP-1, after bromination of the hydroxyl group by thionyl bromide, using DBU as base at room temperature to produce NO-SCP-1 in 57%.

Halloysite is a naturally available clay with a hollow tubular structure, and it is abundant and durable. Metallic nanoparticles supported by halloysite to form nanocomposite materials have huge potential in heterogeneous catalysis. Silver nanoparticles (~10 nm, AgNP) were synthesized inside the lumen of halloysite under green conditions to form Ag@Hal. The nanocomposite was characterized by Transmission Electron Microscopy and Inductively Coupled Plasma Atomic Emmision Spectroscopy and determined to be 6% Ag@Hal (wt/wt). The Ag@Hal nanocomposite exhibited catalytic activity and selectivity for the synthesis of 1,4-disubstituted over the 1,5- disubstituted triazoles under green condition. The reaction also showed enhanced over all yield when the temperature was increased. The 1-benzyl-4-phenyl-1,2,3-triazole was obtained in 58% yield while the 1,5-disubstituted 1,2,3-triazole was isolated in 19% yield.

Rights

The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or in part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.

Available for download on Monday, December 18, 2023

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