Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Abuo‐Rahma, Gamal El‐Din A.; Hassan, Abdelfattah; Hassan, Heba A.; Abdelhamid, Dalia

doi:10.3987/rev-21-956

Cited by 3 publications

(1 citation statement)

References 102 publications

(43 reference statements)

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“…In 1910, Gabriel reported a new synthetic route for the preparation of thiazoles, for which he used the cyclization of acylaminoacetones using diphosphorus pentasulfide at elevated temperatures; many thiazoles with substituents at the C2 or C5 positions can be obtained via this method. There is another method known as the Cook-Heilborn synthesis, which reacts α-aminonitriles/α-aminoamides with carbon disulfide, carbonyl oxysulfide, isocyanates, or dithioacid esters; many thiazoles with substituents at the C5 position can be obtained through this method [29,30]. On the other hand, the spectroscopic characterization by 1 H NMR (Nuclear Magnetic Resonance) shows chemical shifts for thiazole without substituents at 8.9 ppm (H2), 8.0 ppm (H4) and 7.4 ppm (H5), while the 13 C NMR are 154 ppm (C2), 143 pm (C4) and 120 ppm (C5).…”

Section: Synthesis and Characterization Of Thiazolesmentioning

confidence: 99%

Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

et al. 2023

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Throughout human history, bacteria and fungi have caused infections that are difficult to combat. For this reason, countless research groups have developed novel compounds to solve this problem. Thiazole and benzothiazole are present in different structures with interesting biological effects and are used to develop new effective antimicrobial agents. Moreover, nitrogen atoms that are present in this heterocycle allow for coordination with various metals, forming metal complexes that enhance the biological activity of organic ligands that are often used as commercial drugs. This bibliographical review summarizes the copper complexes that use thiazole and benzothiazole as ligands and that report efficient antimicrobial activity against different bacteria and fungi.

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Section: Synthesis and Characterization Of Thiazolesmentioning

confidence: 99%

Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

et al. 2023

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4-Methylthiazole Triggers Apoptosis and Mitochondrial Disruption in HL-60 Cells

Meriç,

Kar,

Kar

2024

Preprint

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Thiazole derivatives are gaining prominence in cancer research due to their potent anti-cancer effects and multifaceted biological activities. Notably, in leukemia research, these compounds are studied for their ability to induce apoptosis, disrupt mitochondrial membrane potential (MMP), and modulate cell signaling pathways. This study focuses on 4-Methylthiazole's effectiveness in inducing apoptosis in HL-60 leukemia cells. It significantly disrupts MMP, activates caspase-3, and promotes cytochrome c release, which are key indicators of apoptosis (**** p < 0.0001, *** p < 0.001, ** p < 0.01, * p < 0.05). Additionally, 4-Methylthiazole reduces CD45 and CD123 surface markers, altering the phenotypic characteristics of leukemia cells (**** p < 0.0001). A high-dose treatment with 4-Methylthiazole significantly increases ROS levels, pointing to elevated oxidative stress and intracellular free radicals, contributing to its cytotoxic effects (*p < 0.05). The study also observed a significant rise in TNF-α levels post-treatment, indicating a pro-inflammatory response that may further inhibit leukemia cell viability. While IL-6 levels remained unchanged, a dose-dependent decrease in IL-10 levels was noted, suggesting a reduction in immunosuppressive conditions within the tumor microenvironment (*p < 0.05). Overall, 4-Methylthiazole targets leukemia cells through multiple apoptotic mechanisms and modifies the immune landscape of the tumor microenvironment, enhancing its therapeutic potential. This study highlights the need for further clinical investigation to fully exploit the potential of thiazole derivatives in leukemia treatment.

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Recent Development in the Synthesis of Thiazoles

Duc

Chung

2022

COS

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Background: Thiazole-containing compounds are widely found in natural products as well as synthetic sources. Many thiazole-based compounds possess a broad spectrum of bioactivities and some of them are well-known drugs in the markets. The use of thiazole derivatives in other fields such as organic materials, cosmetics and organic synthesis has also widely reported. Due to a wide range of applicability, the synthesis of thiazole-containing compounds has attracted extensive interests of chemist and many studies in the synthesis of thiazole skeleton have been reported recently. Objective: This review article will discuss recent studies in the synthesis of thiazoles (from 2012). Beside the well-established Hantzsch thiazole synthesis, a large number of novel methods have been developed for the synthesis of thiazole derivatives. In most cases, reaction mechanisms have also been described. Conclusion: The synthesis of thiazole derivatives has drawn great attention of chemists and many studies in the synthesis of these heterocycles have been reported recently. The classical method, the Hantzsch thiazole synthesis have still received great research interest of chemists. Moreover, many new methods have been established to synthesize thiazole-derived compounds. Unquestionably, more and more approaches to access thiazole skeleton will appear in the literature. Application of established methods for thiazole synthesis to the synthesis of drugs, organic materials, and natural products will probably paid attention

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Synthetic Approaches toward Certain Structurally Related Antimicrobial Thiazole Derivatives (2010-2020)

Cited by 3 publications

References 102 publications

Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

Copper-Coordinated Thiazoles and Benzothiazoles: A Perfect Alliance in the Search for Compounds with Antibacterial and Antifungal Activity

4-Methylthiazole Triggers Apoptosis and Mitochondrial Disruption in HL-60 Cells

Recent Development in the Synthesis of Thiazoles

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