Judging Category

Basic or Experimental Research

Student Rank

Senior

College

Sciences and Mathematics

Description

Melanoma is the 5th most common cancer in both men and women in the USA. It originates in melanocytes, which make the melanin pigment that gives skin its color. While treatable in early stages, melanoma becomes nearly incurable once metastasized. Thiazole derivatives have been recognized in many pharmaceutical classes including anticancer, antimicrobial, antimalarial, anti-tuberculosis, and diuretics. They have long been researched for their natural pharmacological properties and have shown potential to inhibit melanoma cell growth. In this study, catechol-substituted thiazole derivatives were synthesized using the Hantzsch-Thiazole synthesis. A total of 13 novel compounds were made using 2-chlorodihydroxyacetophenone with various catechol-substituted thioureas. Selected derivatives were then acylated using various acid anhydrides to generate ester derivatives with potential prodrug behavior. These compounds, 26 in total, were evaluated using hydrogen (1H), carbon-13 (13C) NMR spectroscopy, and high-resolution mass spectrometry. All the catechol-substituted thiazole derivatives were successfully synthesized in moderate to good yields. Structural characterization using NMR and mass spectrometry confirmed the expected molecular structures for most of the compounds while providing insight into the structures formed by the acylation reactions. These compounds provide insight into future studies to evaluate their potential as anticancer agents in melanoma cell lines.

Disciplines

Medicinal-Pharmaceutical Chemistry

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Synthesis and Characterization of Thiazole Derivatives as Potential Antitumor Agents

Melanoma is the 5th most common cancer in both men and women in the USA. It originates in melanocytes, which make the melanin pigment that gives skin its color. While treatable in early stages, melanoma becomes nearly incurable once metastasized. Thiazole derivatives have been recognized in many pharmaceutical classes including anticancer, antimicrobial, antimalarial, anti-tuberculosis, and diuretics. They have long been researched for their natural pharmacological properties and have shown potential to inhibit melanoma cell growth. In this study, catechol-substituted thiazole derivatives were synthesized using the Hantzsch-Thiazole synthesis. A total of 13 novel compounds were made using 2-chlorodihydroxyacetophenone with various catechol-substituted thioureas. Selected derivatives were then acylated using various acid anhydrides to generate ester derivatives with potential prodrug behavior. These compounds, 26 in total, were evaluated using hydrogen (1H), carbon-13 (13C) NMR spectroscopy, and high-resolution mass spectrometry. All the catechol-substituted thiazole derivatives were successfully synthesized in moderate to good yields. Structural characterization using NMR and mass spectrometry confirmed the expected molecular structures for most of the compounds while providing insight into the structures formed by the acylation reactions. These compounds provide insight into future studies to evaluate their potential as anticancer agents in melanoma cell lines.

 

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