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

Anca-Maria Borcea,Ovidiu Oniga,Ovidiu Crișan,Ioana Ionuț

doi:10.3390/molecules26030624

Abstract

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.

Highlights

Nitrogen-containing heterocyclic compounds play an important role in the drug discovery process, as approximately 75% of FDA (Food and Drug Administration)-approved small-molecule drugs contain one or more nitrogen-based heterocycles [1]
By the reaction of thiourea with alpha-halocarbonyl compounds, monosubstituted or MMMMoooollelelececcucuuullelelesesss2222000022221111,22226666,6xxx2F4FFOOORRRPPPEEEEEERRRRRREEEVVVIIIEdEEWiWWsubstituted 2-aminothiazoles can be obtained, while by using other compounds co44n44tooooaffffi2n222666-6 ing thioamide moieties, such as thiosemicarbazides and thiosemicarbazones, 2-hydrazinothiazole and thiazol-2-yl-hydrazone derivatives can be synthesized in good yields
A new series of 2,5-dichloro thienyl-substituted thiazoles were efficiently obtained by Sarojini et al [53] and their minimum inhibitory concentration (MIC) values against four fungal strains (Aspergillus fumigatus, Aspergillus flavus, Penicillium marneffei, and Trichophyton mentagrophytes) and four bacterial strains (Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa) were determined

Summary

Introduction

Nitrogen-containing heterocyclic compounds play an important role in the drug discovery process, as approximately 75% of FDA (Food and Drug Administration)-approved small-molecule drugs contain one or more nitrogen-based heterocycles [1]. By the reaction of thiourea with alpha-halocarbonyl compounds, monosubstituted or MMMMoooollelelececcucuuullelelesesss2222000022221111,,,,22226666,,,,6xxx2F4FFOOORRRPPPEEEEEERRRRRREEEVVVIIIEdEEWiWWsubstituted 2-aminothiazoles can be obtained, while by using other compounds co44n44tooooaffffi2n222666-6 ing thioamide moieties, such as thiosemicarbazides and thiosemicarbazones, 2-hydrazinothiazole and thiazol-2-yl-hydrazone derivatives can be synthesized in good yields. The short reaction time (10–30 min) and obtaining sufficiently pure final products in good yields are the main advantages of this method This SSpSSccrcchhohheeceemmemmdeeeeu4444r....eCCCCoomooooooakkkkd––––HHeHHeeeieiitiilllblbbpbrrrrooooonsnnnsssissyybyynnlnnetttthhhhteeeoessssiiisisossboooofftffa5555i--n--aaaammmm2ii-inniunnooono----2s222u----mmmmbeeseerrtrrciccctaaauapppptttetotooodttththhhitiiaiahaazzzizooaoollzleeleeossss..l..es, which cannot be synthesized through other approaches such as Hantzsch or Cook–Heilbron synthesis. Asif et al [43] developed a simple, one-pot, efficient method for the synthesis of novel steroidal thiazole derivatives through the condensation reaction of 2-bromoacetophenone, thiosemicarbazide, and steroidal carbonyl compounds (Scheme 12). The reaction took place under microwave heating at 60 ◦C, in ethanol, for 35–45 min, obtaining the target compounds in good yields (80–85%). Synthesis of thiazoles from thiosemicarbazones and α-bromoketones under microwave irradiation

Antimicrobial Activity

Antiprotozoal Activity

Antitumor Activity

Conclusions

48 Results