Thiazole: A Review on Chemistry, Synthesis and Therapeutic Importance of its Derivatives

Abstract

Thiazole, a unique heterocycle containing sulphur and nitrogen atoms, occupies an important place in medicinal chemistry. It is an essential core scaffold present in many natural (Vitamin B1- Thiamine) and synthetic medicinally important compounds. The versatility of thiazole nucleus demonstrated by the fact that it is an essential part of penicillin nucleus and some of its derivatives which have shown antimicrobial (sulfazole), antiretroviral (ritonavir), antifungal (abafungin), antihistaminic and antithyroid activities. The synthetic importance of thiazole derivatives, its reduced forms and condensed derivatives have been increased much by their recent applications as anticancer (tiazofurin), anthelmintic, vulcanising accelerators (mercaptobenzothiazole) and photographic sensitizers. Thiazole chemistry has developed steadily after the pioneering work of Hofmann and Hantsch. Bogert and co-workers made significant contribution to expand this field. Mills established the importance of thiazole ring in cyanine dyes which is used as photographic sensitizer. Benzothiazole, a fused derivative of thiazole have also proved its commercial value. Present review describes chemical and biological importance of thiazole and its condensed derivatives with an emphasis on recent developments.

N-Propargylamines: versatile building blocks in the construction of thiazole cores

“…Moreover, thiazoles are widely applied as pesticides and dyes [25]. As a consequence, many routes for the synthesis of thiazole derivatives are reported in the literature [26–33]. Among them, the Hantzsch thiazole synthesis (condensation of α-haloketones with thioamides) is the most efficient and straight forward procedure [34–43].…”

Synthesis of novel cyclopeptides containing heterocyclic skeletons

“…In addition, thiazole derivatives have applications as anticancer drugs (tiazofurin), anthelmintics, vulcanizing accelerators (mercaptobenzothiazole) and photographic sensitizers. 117 Since oxazoles and thiazoles were naturally discovered in the backbones of cyclopeptides, conrming that their presence can impose conformational restrictions on cyclic peptides, many studies have been performed on these heterocycles. 118,119 Condensation between side chain cysteine thiols or threonine/serine hydroxy groups and neighboring amide bonds affords heterocyclic rings, as illustrated in Scheme 18, resulting in highly constrained pseudo-boat or saddle-shaped macrocycles.…”

Synthesis of new thiazole and thiazolyl derivatives of medicinal significant-a short review

“…The synthetic significance of thiazole derivatives have been increased much by their recent medicinal applications as anticancer, antifungal, anti-inflammatory, antihypertensive, anti-HIV, anticonvulsant and antidiabetic thus, thiazole chemistry has developed in steady state as we can see in many recent literatures. 21,22 Based on this; many recent articles showed the use of palladium(II) acetate which catalyzes a really selective coupling of 4-substituted 2-aminothiazoles from vinyl azides and potassium thiocyanate, whereas iron(III) bromide supports the formation of 4-substituted 5-thiocyano-2-aminothiazoles. 23 In addition, a copper-catalyzed reaction of oxime acetates with isothiocyanates gives various 4-substituted and 4,5-disubstituted 2-aminothiazoles under mild reaction conditions via copper-catalyzed N-O bond splitting, activation of vinyl sp2 C-H bonds, and C-S/C-N bond formations.…”