Thiazole Ring—A Biologically Active Scaffold

Petrou, Anthi; Fesatidou, Maria; Geronikaki, Athina

doi:10.3390/molecules26113166

Cited by 156 publications

(109 citation statements)

References 271 publications

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“…Compounds containing dihydrothiazoles in their structure exhibit a broad spectrum of biological activity, including antiproliferative, antibacterial, anti-inflammatory, antiparasitic, and antifungal activity [20,21]. Thiazole derivatives are also found as new enzyme inhibitors, for example Biovitrum BVT-2733, Biovitrum BVT-14225, AMG-221, and Amgen 2922 can inhibit 11β-hydroxysteroid dehydrogenase type 1 (Figure 1) [22][23][24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1—Synthesis, Molecular Docking and In Vitro Studies

Studzińska

Kupczyk

Płaziński

et al. 2021

IJMS

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A common mechanism in which glucocorticoids participate is suggested in the pathogenesis of such metabolic diseases as obesity, metabolic syndrome, or Cushing’s syndrome. The enzyme involved in the control of the availability of cortisol, the active form of the glucocorticoid for the glucocorticoid receptor, is 11β-HSD1. Inhibition of 11β-HSD1 activity may bring beneficial results for the alleviation of the course of metabolic diseases such as metabolic syndrome, Cushing’s syndrome or type 2 diabetes. In this work, we obtained 10 novel 2-(adamantan-1-ylamino)thiazol-4(5H)-one derivatives containing different substituents at C-5 of thiazole ring and tested their activity towards inhibition of two 11β-HSD isoforms. For most of them, over 50% inhibition of 11β-HSD1 and less than 45% inhibition of 11β-HSD2 activity at the concentration of 10 µM was observed. The binding energies found during docking simulations for 11β-HSD1 correctly reproduced the experimental IC50 values for analyzed compounds. The most active compound 2-(adamantan-1-ylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one (3i) inhibits the activity of isoform 1 by 82.82%. This value is comparable to the known inhibitor-carbenoxolone. The IC50 value is twice the value determined by us for carbenoxolone, however inhibition of the enzyme isoform 2 to a lesser extent makes it an excellent material for further tests.

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Section: Introductionmentioning

confidence: 99%

Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1—Synthesis, Molecular Docking and In Vitro Studies

Studzińska

Kupczyk

Płaziński

et al. 2021

IJMS

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“…As a result, its derivatives have been effectively applied in many pharmacological fields, such as antimicrobial, antitumor, antioxidant, antitubercular, anticonvulsant, anti-inflammatory, diuretic, and neuroprotective agents. 21 In addition, the thiazole ring acts as the main active ingredient in many promising biomolecules, pro-drugs, and clinical drugs. 14 This motivated us to fabricate novel room-temperature thiazolium ILs for chemotherapeutic applications.…”

Section: Introductionmentioning

confidence: 99%

Fine-tuning of the pharmacological potential of novel thiazolium ionic liquids by anion alteration

et al. 2022

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“…Natural and unnatural thiazole compounds have been widely explored by synthetic organic and medicinal chemists because of their broad range of biological activities, including antioxidant, analgesic, antimicrobial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic activities [5][6][7]. As part of our research interest in biologically active natural products, and because of their interesting structural features, we considered peganumals as attractive synthetic targets.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Confirmation of the Thiazole Alkaloids Derived from Peganum harmala L.

Sim

Han

2021

Applied Sciences

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Peganumal A and B are thiazole alkaloids isolated from the seeds of Peganum harmala L. Thiazole moieties are rarely found in natural products, but diverse compounds possessing thiazole moieties have attracted attention owing to their broad range of biological activities. Peganumals are the first natural thiazole compounds isolated from the genus Peganum. It was difficult to define the exact structure of peganumal A via spectroscopic analysis. In this paper, we report the first total synthesis of peganumal A and B. The 5-benzylthiazole skeleton possessing methyl or hydrogen at the 2-position of the peganumals was efficiently constructed via the Hantzsch thiazole synthesis of the α-bromoaldehyde intermediate. Moreover, the spectral data of the synthetic 2H–thiazole compound were identical to those previously reported for peganumal A. The synthesis allowed the confirmation of the structure of peganumal A.

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Thiazole Ring—A Biologically Active Scaffold

Cited by 156 publications

References 271 publications

Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1—Synthesis, Molecular Docking and In Vitro Studies

Novel 2-(Adamantan-1-ylamino)Thiazol-4(5H)-One Derivatives and Their Inhibitory Activity towards 11β-HSD1—Synthesis, Molecular Docking and In Vitro Studies

Fine-tuning of the pharmacological potential of novel thiazolium ionic liquids by anion alteration

Synthesis and Structural Confirmation of the Thiazole Alkaloids Derived from Peganum harmala L.

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