Organic Chemistry Commons^™

Structure Activity Relationship (Sar) Studies Of Neurotoxin Quinoline-Derivatives, Dylan Smeyne

Honors College Theses

Structure activity relationship (SAR) studies are performed in order to identify the core structure that is responsible for the biological activity of an organic molecule. Recently, we have synthesized a drug prototype which contains several functional groups, such as an alcohol, an ester, a fluorine, and an aromatic ring. While studying in vivo toxicity of this molecule in zebrafish (Danio rerio) embryo, we observed that it has a unique biological activity that causes a sudden inactivity in embryo movement. Continued investigation revealed that this molecule blocks sodium channels in neurons causing a temporary anesthesia in Danio rerio embryo. The biological …

174— Developing Oxidation Of Alcohols In Sand, John Lepore, Stephanie Alvarez Merlos, Katelynn Dux, Theresa Lam

GREAT Day Posters

We present the oxidation of alcohols into aldehydes and ketones using (NH4)2Cr2O7 in sand. Several alcohols undergo oxidation using an appropriate solvent to afford aldehyde and ketones in good yields. The reactions were analyzed by TLC, 1H and 13C-NMR. The developed reaction is also compared to reactions done using silica gel.

Synthesized Tripodal Amine As Potential Anti-Cancer Therapeutic, Abigail G. Mcnamee

Honors College Theses

Cancer remains a prevalent disease today. This disease may manifest itself in many different ways and affect a variety of tissues with everything from the brain to the blood. With this wide diversity of cancer types, treatment can be complicated since there is not a “one size fits all” treatment for the disease. Surgery, radiation, and chemotherapy are all options that must be weighed with their benefits and side effects. Ultimately though, there are not enough effective treatment options available for every type of cancer. This leaves many with the grim prognosis of never being cured. With this clear need …

Identification Of Histone H4-Based Peptoids As Inhibitors Of Prmt1, Megan Demart, Molly Dubose, Sarah Mann, Corey Causey Phd, Bryan Knuckley Phd

Showcase of Osprey Advancements in Research and Scholarship (SOARS)

Protein Arginine Methyltransferases (PRMTs) are a family of 11 mammalian enzymes characterized by the post-translational methylation of arginine residues in the histone tail. The majority of the 11 members of the PRMT family are divided into two main types, Type I and Type II. PRMT1, the major Type I isozyme, catalyzes the formation of asymmetrically dimethylated arginine (ADMA). PRMT1 activates transcription of cancer genes. Peptoids, or poly-N-substituted glycine’s are a class of oligomers whose side chains are appended to the nitrogen atom of the peptide backbone rather than the alpha carbon. Kinetic parameters were conducted for both peptide and peptoid …

New Synthetic Methodology Using Base-Assisted Diazonium Salts Activation And Gold Redox Catalysis, Abiola Azeez Jimoh

USF Tampa Graduate Theses and Dissertations

Over the past two decades, homogeneous Au(I) catalysis has been a valuable synthetic tool for activating a series of unsaturated carbon-carbon bonds towards nucleophilic attack. Despite this progress, Au(I/III) redox chemistry has not been well explored. This is largely due to the challenges associated with the high oxidation potential of gold. Hence, the need for an efficient and safe method for Au oxidation.

Herein, a base-assisted diazonium salt activation has been used to facilitate Au redox reactions under mild reaction conditions. This oxidative coupling method afforded functional isoxazolines with good to excellent yields, while the alternative photoactivation method provided trace …

Monitoring And Identifying The Rhodamine 6g-Hydroxide Ion Reaction Using In-Situ, Surface-Enhanced Raman Spectroscopy, Ryan Lamb

Masters Theses & Specialist Projects

An effective method for monitoring chemical reactions is necessary to better understand their mechanisms and kinetics. Effective reaction monitoring requires a spectroscopy technique with fast data acquisition, high sensitivity, structure-to-spectrum correlation, and low solvent interference. Surface-enhanced Raman spectroscopy (SERS) provides these features, which makes it a valuable tool for monitoring reactions. To obtain the Raman enhancement, metallic nanostructures typically made of silver or gold are aggregated using a salt. The nanoparticles aggregates must then be stabilized using a surfactant to use this method in situ due to eventual nanoparticle precipitation. In this study, gold nanoparticles stabilized with sodium dodecyl sulfate …

Dissipation Of Benzobicyclon And Benzobicyclon Hydrolysate In A Louisiana Rice Field, Xavier Poole

LSU Master's Theses

Pesticide resistance in rice fields is an ongoing issue that has resulted in the development and use of pesticides with new modes of action. Benzobicyclon is the first registered hydroxyphenylpyruvate(HPPD)-inhibiting pesticide in the United States and has gained attention as a resistance management strategy to control weed pests in rice fields. Understanding the environmental fate and dissipation mechanisms of benzobicyclon is important due to the unique rotation of rice and crayfish in Louisiana on the same fields. Benzobicyclon persistence into the crayfish growing seasons may lead to unintended consequences for crayfish growth and production, assuming there is toxicity to crawfish. …

Assessing The Correlation Of Microscopy-Based And Volumetry-Based Measurements For Resin Swelling In A Range Of Potential Greener Solvents For Spps, Jordan K. Magtaan, Marc Devocelle, Fintan Kelleher

Articles

The degree of resin swelling in a particular solvent system is one of the critical parameters for SPPS, and for solid phase synthesis, in general. Methods used for measuring the degree of resin swelling include microscopy-based and volumetry-based methods. This study describes, and compares, the use of both methods for a number of commercially available resins commonly used in SPPS, with a range of solvents which have been identified in the literature as “greener” than DCM, DMF and NMP. The results were analysed by statistical methods and a significant correlation between the two distinct methods has been demonstrated for the …

Synthesis Of 12-Membered Tetra-Aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups, Akop Yepremyan, Magy A. Mekhail, Brian P. Niebuhr, Kristof Pota, Nishanth Sadagopan, Timothy M. Schwartz, Kayla N. Green

Biology, Chemistry, and Environmental Sciences Faculty Articles and Research

The number of substituted pyridine pyridinophanes found in the literature is limited due to challenges associated with 12-membered macrocycle and modified pyridine synthesis. Most notably, the electrophilic character at the 4-position of pyridine in pyridinophanes presents a unique challenge for introducing electrophilic chemical groups. Likewise, of the few reported, most substituted pyridine pyridinophanes in the literature are limited to electron-donating functionalities. Herein, new synthetic strategies for four new macrocycles bearing the electron-withdrawing groups CN, Cl, NO₂, and CF₃ are introduced. Potentiometric titrations were used to determine the protonation constants of the new pyridinophanes. Further, the influence of …

New Catalytic Reactions In Carbohydrate Chemistry, Scott Geringer

Dissertations

Carbohydrates or sugars are some of the most diverse and abundant biological molecules. They are involved in a multitude of processes in the body such as fertilization, cell-cell communication, and cancer metathesis. Because of these vital functions, the study of sugars is rapidly growing field. The field however is limited due to the complex nature of sugars which results in difficulties in obtaining large quantities for study.

Protecting group manipulation is a large emphasis area in carbohydrate chemistry due to the need to selectively protect different functional groups of each molecule during synthesis. Catalytic and selective cleavage of protecting groups …

Gram-Scale Synthesis Of 2,5-Difluoro-7,7,8,8-Tetracyanoquinodimethane (F2-Tcnq), En Chih Liu, Joseph J. Topczewski

Chemistry Faculty Research & Creative Works

The molecule 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (F2-TCNQ) is an organic semiconductor with many promising properties, including high charge mobility (μ). However, an efficient gram-scale synthesis of F2-TCNQ has not been fully documented. Herein, we report a synthesis of F2-TCNQ via a three-step sequence that affords F2-TCNQ in 58% cumulative yield. This synthesis was used to prepare more than 1 g of F2-TCNQ.

Polyphenols In Alzheimer’S Disease And In The Gut–Brain Axis, V. Prakash Reddy, Puspa Aryal, Sara Robinson, Raheemat Rafiu, Mark Obrenovich, George Perry

Chemistry Faculty Research & Creative Works

Polyphenolic antioxidants, including dietary plant lignans, modulate the gut–brain axis, which involves transformation of these polyphenolic compounds into physiologically active and neuroprotector compounds (called human lignans) through gut bacterial metabolism. These gut bacterial metabolites exert their neuroprotective effects in various neurodegenerative diseases, such as Alzheimer's disease (AD) and Parkinson's disease (PD), and also have protective effects against other diseases, such as cardiovascular diseases, cancer, and diabetes. For example, enterolactone and enterodiol, the therapeutically relevant polyphenols, are formed as the secondary gut bacterial metabolites of lignans, the non-flavonoid polyphenolic compounds found in plant-based foods. These compounds are also acetylcholinesterase inhibitors and …

Synthesis And Antitumor Activity Of Potentially Tumor Targeting Analogues Of The Tetrahydrofuran Containing Acetogenins, Patricia Gonzalez Periche

Dissertations, Theses, and Capstone Projects

The tetrahydrofuran containing acetogenins (THF-ACGs) are a naturally occurring class of compounds with potent toxicity against a broad range of tumors, including multidrug resistant (MDR) strains. However, the equally high toxicity to normal cells presents a hurdle for their clinical advancement. This study entails synthetic and tumor targeting strategies that are relevant to their therapeutic development.

Chapter 1 presents a review of the synthesis and biological activity of the THF-ACGs. Chapter 2 covers a modular approach for the synthesis of libraries of THF-ACGs. This strategy is illustrated in the synthesis of C-10 epimers of 4-deoxyannonomontacin (4-DAN), one of the more …

Synthesis Of Unsymmetrical Bidentate Ligands From Secondary Phosphine Oxides, Malachy J. Brink, Ryan Anderson

Student Research, Papers, and Creative Works

Stereochemistry is a key component in the field of asymmetric catalysis. The properties of a molecule can be drastically changed with the change of one stereocenter. Typically, chirality is imparted to a metal by the ligand. "Chiral-at-metal" compounds are unique because the metal complex is chiral, but the ligands are not. Phosphine ligands are notoriously difficult to work with (pyrophoric, toxic, prone to oxidation). The goal of this research was to prepare unsymmetrical bidentate ligands using secondary phosphine oxides, which are air-stable and easy to handle on the benchtop.

Controlling Transition Metal-Catalyzed Alkyne Annulations Utilizing Polarized Ynol Ethers, Brandon L. Coles-Taylor

Electronic Theses and Dissertations

Transition metal-catalyzed alkyne annulations have developed into incredibly powerful synthetic tools over there the past quarter century. These reactions provide rapid access to important organic scaffolds such as indole, quinoline, isoquinoline, indene, and isocoumarin scaffolds. Transition metal mediated alkyne annulations have proven invaluable in synthetic fields, such as natural product total synthesis, by offering efficient pathways to otherwise synthetically difficult to access substrates.

Foundational works performed by chemist such as Larock, Ackermann, Satoh, and Miura have been established through relying upon the usage of symmetrical alkynes. When unsymmetrical alkynes are used in annulation processes mixtures of regioisomers are often isolated. …

Development Towards An Ethylene Sensing Artificial Metalloenzyme, Mitchell Lee Ellinwood

Electronic Theses and Dissertations

Ethylene (ethene) is the essential ripening hormone for climacteric plants, and consequently its detection and quantification is of considerable interest to the horticulture industry. Its detection however is a non-trivial pursuit, traditionally requiring expensive and inaccessible instrumentation that fail to provide in vivo information about ethylene. A ruthenium based fluorescent probe for the selective detection of ethylene has recently been developed, and it was envisioned that this probe could be made biocompatible by encasing it within a protein scaffold making it an artificial metalloenzyme. To this end biotinylated N-heterocyclic carbenes (NHCs) were synthesized, which can be appended onto the ruthenium …

Development And Application Of Chemical Tools To Identify Kinase-Substrate Interactions, Aparni Kithulgoda Gamage

Wayne State University Dissertations

Post translational modifications regulate a variety of biological processes inside the cell.Protein phosphorylation is one such PTM modification catalyzed by protein kinases, which aid to transfer a signal from one place to another inside the cell. However, irregularities in kinase-mediated signaling are often implicated in many diseases, making kinases effective drug targets. To understand kinase-related disease formation and to discover drugs to treat these diseases, it is crucial to have a clear understanding on kinase-mediated cell signaling networks. A current gap in the kinase biology field is a lack of tools to identify which kinase phosphorylates which protein substrate inside …

Green Chemistry: The Oxidation Of Benzaldehyde Using Atmospheric Oxygen And N-Heterocyclic Carbenes As Catalysts, Alex Brody, John Morgan

Student Research Poster Presentations 2020

Oxidation is a vital process in organic and biochemical reactions. In particular, the oxidation of aromatic aldehydes to carboxylic acids and esters is a vital process used in many different environments. Benzaldehyde is one common subject of this type of reaction, used in the synthesis of benzoic acid and benzoate derivatives. Unfortunately, the industrial synthesis of these compounds uses harmful heavy metal oxidants such as Chromium(VI) and Manganese(VII), which are very harmful to the environment. We proposed to eliminate these pollutants by using atmospheric oxygen and an organic catalyst in a solvent free reaction. This reaction would then be microwaved …

Chemistry In Medicine, Olivia Visaggio, Alyssa Bondi, Matthew Gillingham, Hailey Loughlin

Student Research Poster Presentations 2020

The chemistry behind medicine is important and necessary to study many different drugs and their effects. In this project, we focused on the chemical composition and mechanisms of various drugs. The drugs we focused on include Opioids, NSAIDs, and other medications, such as Benzodiazepines and antibiotics. For each drug, we provided its structure as well as the functional groups, which include a part of a molecule that is recognized based on its arrangement of atoms. Organic Chemistry provides individuals with an understanding of various organic compounds, and this field of study is important as it explains the ways in which …

Influence Of Conformational Restriction On The Antibacterial Activity And Ribosomal Selectivity Of Aminoglycoside Antibiotics, Michael Gabriel Pirrone

Wayne State University Dissertations

The ever-increasing threat posed by multidrug-resistant infectious bacteria necessitates

the development of novel antibiotics. Aminoglycoside antibiotics are growing in interest due to

their broad spectrum of activity, lack of known drug related allergies, low manufacturing cost,

and their well-studied mechanism of action. The simplification of rational drug design due to the

well-studied mechanism of action is the key to overcoming the issues presented by these drugs,

namely ototoxicity and nephrotoxicity.

A study of the effect of the conformation of the aminoglycoside ring I side chain is

described wherein it was discovered that an increase in a particular conformation augments the …