Review of the synthesis and biological activity of thiazoles

Ali, Sukinah H.; Sayed, Abdelwahed R.

doi:10.1080/00397911.2020.1854787

Cited by 127 publications

(76 citation statements)

References 81 publications

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“…The condensation reactions occur through imino thioether and hydroxythiazoline intermediates, which are sometimes stable and isolable. The alpha-halocarbonyl component may be represented by alpha-haloketones and alpha-haloesters [32,33]. Another method of obtaining thiazoles is represented by Gabriel synthesis, which consists of the cyclization reaction of acylaminocarbonyl compounds and a stoichiometric amount of phosphorus pentasulfide at 170 °C (Scheme 2) [28,34].…”

Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

“…Cook-Heilbron synthesis leads to 2,4-disubstituted 5-aminothiazole derivatives by the reaction of an α-aminonitrile and dithioacids or esters of dithioacids, carbon disulfide, carbon oxysulfide, or isothiocyanates under mild reaction conditions (Scheme 3). When carbon disulfide is used in the reaction, 5-amino-2-mercaptothiazole compounds are formed (Scheme 4) [32,33]. Lingaraju et al [35] efficiently synthesized a series of 4,5-disubstituted thiazole derivatives from active methylene isocyanides and methyl carbodithioates (Scheme 5).…”

Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

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An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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Thiazole, a five-membered heteroaromatic ring, is an important scaffold of a large number of synthetic compounds. Its diverse pharmacological activity is reflected in many clinically approved thiazole-containing molecules, with an extensive range of biological activities, such as antibacterial, antifungal, antiviral, antihelmintic, antitumor, and anti-inflammatory effects. Due to its significance in the field of medicinal chemistry, numerous biologically active thiazole and bisthiazole derivatives have been reported in the scientific literature. The current review provides an overview of different methods for the synthesis of thiazole and bisthiazole derivatives and describes various compounds bearing a thiazole and bisthiazole moiety possessing antibacterial, antifungal, antiprotozoal, and antitumor activity, encouraging further research on the discovery of thiazole-containing drugs.

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Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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“…The chemistry of thiazoles is currently widely developed due to the relatively easy synthesis of a wide range of compounds, which enables studying the relationship between their structure and properties [12,13]. Due to the nonlinear optical properties (NLO) of the thiazole system, it is used in optical devices such as photovoltaic detectors or light-emitting diodes [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Physicochemical Characterization of Novel Dicyclopropyl-Thiazole Compounds as Nontoxic and Promising Antifungals

et al. 2021

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There is a need to search for new antifungals, especially for the treatment of the invasive Candida infections, caused mainly by C. albicans. These infections are steadily increasing at an alarming rate, mostly among immunocompromised patients. The newly synthesized compounds (3a–3k) were characterized by physicochemical parameters and investigated for antimicrobial activity using the microdilution broth method to estimate minimal inhibitory concentration (MIC). Additionally, their antibiofilm activity and mode of action together with the effect on the membrane permeability in C. albicans were investigated. Biofilm biomass and its metabolic activity were quantitatively measured using crystal violet (CV) staining and tetrazolium salt (XTT) reduction assay. The cytotoxic effect on normal human lung fibroblasts and haemolytic effect were also evaluated. The results showed differential activity of the compounds against yeasts (MIC = 0.24–500 µg/mL) and bacteria (MIC = 125–1000 µg/mL). Most compounds possessed strong antifungal activity (MIC = 0.24–7.81 µg/mL). The compounds 3b, 3c and 3e, showed no inhibitory (at 1/2 × MIC) and eradication (at 8 × MIC) effect on C. albicans biofilm. Only slight decrease in the biofilm metabolic activity was observed for compound 3b. Moreover, the studied compounds increased the permeability of the membrane/cell wall of C. albicans and their mode of action may be related to action within the fungal cell wall structure and/or within the cell membrane. It is worth noting that the compounds had no cytotoxicity effect on pulmonary fibroblasts and erythrocytes at concentrations showing anticandidal activity. The present studies in vitro confirm that these derivatives appear to be a very promising group of antifungals for further preclinical studies.

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“…Besides, substituted thia-zole derivatives are well known as COX-2 [11,12], serine protease urokinase (uPa) inhibitors [13], adenosine A1 receptor [14] and metabotropic glutamate receptor 5 (mGluR5) antagonists [15]. Noteworthy, the thiazole cycle's uniqueness in the construction of new druglike molecules is based on the wide possibility of their functionalization providing different classes of condensed and non-condensed thiazoles [16][17][18][19][20]. Moreover, the structural modification of this heterocycle allows obtaining compounds with a new pharmacological profile, increased activity or reduced toxicity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of biological activity of 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones

et al. 2021

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To accomplish the synthesis and screening of anticancer and antimicrobial activities of 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones 2-10. Methods. The in vitro anticancer activity of compounds 4, 6, 8-10 has been established by DTP(Developmental Therapeutics Program) of the National Cancer Institute. The antibacterial and antifungal activities of synthesized thiazole-based derivatives were evaluated in vitro with the agar diffusion and broth microdilution methods to wards Gram-positive, Gram-negative bacteria and yeasts. For the synthesized compounds, the in silico drug-likeness screening using SwissADME online server is reported. Results. The novel 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones were synthesized from 1-[2-amino-4-methylthiazol-5-yl]ethanones and various aromatic aldehydes in the Claisen-Schmidt condensation. The synthesized compound 9 was moderately active against the leukemia CCRF-CEM and HL-60(TB), renal cancer UO-31 and breast cancer MCF7 cell lines. The antimicrobial screening led to identification of the active compound 10 against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans. Conclusions. The results obtained herein provide a platform for structure-based optimization of these newly identified thiazole-based compounds for the anticancer and antibacterial drug design.

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Review of the synthesis and biological activity of thiazoles

Cited by 127 publications

References 81 publications

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

Synthesis and Physicochemical Characterization of Novel Dicyclopropyl-Thiazole Compounds as Nontoxic and Promising Antifungals

Synthesis and evaluation of biological activity of 1-[2-amino-4-methylthiazol-5-yl]-3-arylpropenones

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