Abstract
Many novel thiazole derivatives were designed and synthesized using 4-phenylthiazol-2-amine. The reactivity of the latter compound toward different chemical reagents was studied. The structure of the newly synthesized compounds was established based on elemental analysis and spectral data. Furthermore, twenty compounds of the synthesized systems were selected and evaluated in (µM) as significant anticancer agents towards three human cancer cell lines [MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer)] and normal fibroblasts human cell line (WI-38). The results showed that compounds 9 and 14a displayed higher effeciency than the reference doxorubicin.
Highlights
Great concern has been recently focused on the development of heterocyclic compound bearing 1,3-thiazole ring system, which has been identified as a central structural element of several biologically active natural products such as thiamine vitamin B, and pharmacologically active substances in a large number of drugs as antibacterial,[1,2] antifungal,[3,4] antiviral,[5,6,7] anti-inflammatory,[8,9] anticancer,[10,11,12,13,14] anti-HIV,[15,16,17] anti-oxidant[18,19] and analgesic drugs.[20,21]
Some of the examples of such organic synthesis methods were: the reaction between haloketones and thio-amides (Hantzsch thiazole synthesis, 1889),22,23 2-acylamino-ketones reacting with phosphorus pentasulfide (Robinson–Gabriel synthesis),[24,25,26] α-aminonitrile with carbon disulfide (Cook–Heilbron synthesis),[27] and the addition of a thiazole anion to an aromatic nitrile,[28] certain thiazoles can be accessed through the application of the Herz reaction.[29]
Various biosynthesis routes lead to the development of the thiazole ring system as required for the formation of thiamine.[30]
Summary
Great concern has been recently focused on the development of heterocyclic compound bearing 1,3-thiazole ring system, which has been identified as a central structural element of several biologically active natural products such as thiamine vitamin B, and pharmacologically active substances in a large number of drugs as antibacterial,[1,2] antifungal,[3,4] antiviral,[5,6,7] anti-inflammatory,[8,9] anticancer,[10,11,12,13,14] anti-HIV,[15,16,17] anti-oxidant[18,19] and analgesic drugs.[20,21]Both classical and non-classical synthetic methods approaches were used to synthesize thiazole derivatives. Some of the examples of such organic synthesis methods were: the reaction between haloketones and thio-amides (Hantzsch thiazole synthesis, 1889),22,23 2-acylamino-ketones reacting with phosphorus pentasulfide (Robinson–Gabriel synthesis),[24,25,26] α-aminonitrile with carbon disulfide (Cook–Heilbron synthesis),[27] and the addition of a thiazole anion to an aromatic nitrile,[28] certain thiazoles can be accessed through the application of the Herz reaction.[29] various biosynthesis routes lead to the development of the thiazole ring system as required for the formation of thiamine.[30] Thiazole derivatives were widely used in dyeing, for example, anthroquinone dyes that contain benzothiazole moiety, such as Algol Yellow 8 They were used as non-steroidal anti-inflammatory drugs (NSAID) like Meloxicam (Figure 1), antiretroviral drugs (Ritonavir), antineoplastic drugs (Tiazofurin), antifungal drugs (Abafungin), and antimicrobial drugs (Sulfathiazol). Modifications of the thiazole ring have proven high effectiveness with improved potency and lesser toxicity
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