The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship was written by Buchholz, Mirko;Heiser, Ulrich;Schilling, Stephan;Niestroj, Andre J.;Zunkel, Katrin;Demuth, Hans-Ulrich. And the article was included in Journal of Medicinal Chemistry in 2006.Computed Properties of C9H10N2O2S This article mentions the following:
The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the mols., which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Computed Properties of C9H10N2O2S).
5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Computed Properties of C9H10N2O2S
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica