Importance of substituents in ring opening: a DFT study on a model reaction of thiazole to thioamide was written by Bai, Xue;Qin, Dan;Yang, Lijun. And the article was included in Journal of Molecular Modeling in 2021.Recommanded Product: 2-Methylthiazol-5-amine This article mentions the following:
Thiazole ring is an important active mol. skeleton of drugs. Thiazole in natural products and drugs are usually harmlessly eliminated. However, hepatotoxic reactions may occur due to the biol. activation of thiazole to produce reactive thioamide. A typical example is hepatotoxic sudoxicam and safety meloxicam. The only structural difference between them is a Me group on C5 position of thiazole in meloxicam. The mol. basis for the difference remains unknown and the bioactivation mechanism of the thiazole ring is still obscure. Quantum chem. calculations were performed to elucidate the activation mechanism of the thiazole ring under P 450 catalysis, and the influence of the substituents on the activation pathways of thiazole ring was also studied. The calculated results show that the activation of thiazole is closely related to the substituents on the thiazole and spin state of Cpd I. The thiazole and substituted thiazole directly open the ring when catalyzed by doublet spin state Cpd I that catalyzed by the quartet spin state Cpd I can open the ring directly or indirectly, which is related to the substituents. Thiazoles modified with electron-donating substituents mainly undergo direct ring opening, while thiazoles modified with electron-withdrawing groups or weak electron-donating groups mainly undergo indirect ring-opening process accompanied by intermediate formation. The research results laid the foundation for the design of thiazole ring drugs, and also laid a theor. foundation for the study of reducing the toxicity of thiazole ring drugs. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Recommanded Product: 2-Methylthiazol-5-amine).
2-Methylthiazol-5-amine (cas: 89281-44-7) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Recommanded Product: 2-Methylthiazol-5-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica