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.
Recommended Citation
Bajaber, Majed Abdullah, "Design and Synthesis of Novel NO-Drug Hybrid Compound and Green Catalytic Activity Evaluation of Synthesized Silver Nanoparticles-Halloysite Nanocomposite" (2020). University of New Orleans Theses and Dissertations. 3004.
https://scholarworks.uno.edu/td/3004
Included in
Inorganic Chemistry Commons, Medicinal-Pharmaceutical Chemistry Commons, Organic Chemicals Commons, Organic Chemistry Commons
Rights
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