Application In Synthesis of trans-4-AminocyclohexanolIn 2021 ,《New quinolinone O-GlcNAc transferase inhibitors based on fragment growth》 appeared in Frontiers in Chemistry (Lausanne, Switzerland). The author of the article were Weiss, Matjaz; Loi, Elena M.; Sterle, Masa; Balsollier, Cyril; Tomasic, Tihomir; Pieters, Roland J.; Gobec, Martina; Anderluh, Marko. The article conveys some information:
Herein, the extension of 2-oxo-1,2-dihydroquinoline-4-carboxamide derivatives with several new fragments was reported. Compound I [R = CO2Et; n = 0] was identified as the most potent fragment with an IC50 value of 116.0μM. If compared with the most potent inhibitor of the first series, compound I [R = CO2H; n = 1] (IC50 = 117.6μM), it was concluded that the new fragments did not improve OGT inhibition remarkably. Therefore, compound I [R = CO2H; n = 1] was used as the basis for the design of a series of compounds with the elongation toward the O-GlcNAc binding pocket as the free carboxylate allowed easy conjugation. 2-Oxo-N-(4-(pyridin-4-ylcarbamoyl)benzyl)-1,2-dihydroquinoline-4-carboxamide with an IC50 value of 144.5μM showed the most potent OGT inhibition among the elongated compounds, but it lost inhibition potency when compared to the UDP mimetic compound I [R = CO2H; n = 1]. Therefore it was assumed that the binding of the compounds in the O-GlcNAc binding pocket was likely not crucial for OGT inhibition. Furthermore, evaluation of the compounds with two different assays revealed that some inhibitors most likely interfere with the com. available UDP-Glo glycosyltransferase assay, leading to false pos. results. This observation called for caution, when evaluating UDP mimetic as OGT inhibitors with the UDP-Glo glycosyltransferase assay, as misinterpretations can occur. The experimental process involved the reaction of trans-4-Aminocyclohexanol(cas: 27489-62-9Application In Synthesis of trans-4-Aminocyclohexanol)
trans-4-Aminocyclohexanol(cas: 27489-62-9) belongs to anime. Primary amines having a tertiary alkyl group (R3CNH2) are difficult to prepare with most methods but are made industrially by the Ritter reaction. In this method a tertiary alcohol reacts with hydrogen cyanide (HCN) in the presence of a concentrated strong acid; a formamide, RNH―CHO, is formed first, which then undergoes hydrolysis.Application In Synthesis of trans-4-Aminocyclohexanol
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