Shimizu, Kazuo; Fujikura, Hideki; Fushimi, Nobuhiko; Nishimura, Toshihiro; Tatani, Kazuya; Katsuno, Kenji; Fujimori, Yoshikazu; Watanabe, Shinjiro; Hiratochi, Masahiro; Nakabayashi, Takeshi; Kamada, Noboru; Arakawa, Koichi; Hikawa, Hidemasa; Azumaya, Isao; Isaji, Masayuki published an article in 2021. The article was titled 《Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor》, and you may find the article in Bioorganic & Medicinal Chemistry.Name: Ethyl 3-oxopentanoate The information in the text is summarized as follows:
We optimized the structure of an active metabolite (1) of WAY-123783, which was obtained from mouse urine after oral administration, to improve selectivity for SGLT2 and oral bioavailability. O-glucoside derivative 24 (remogliflozin etabonate) was subsequently identified as a potent, highly selective, and orally available SGLT2 inhibitor. In the present study, a series of pyrazole-O-glucoside derivatives of the active metabolite of WAY-123783 was designed and synthesized to identify novel orally available selective SGLT2 inhibitors. SAR studies revealed that the substituent at 5-position of the pyrazole ring could affect the intestinal stability of the glucosidic linkage, and that a 5-meth-ylpyrazole bearing 4-isopropoxybenzyl group was the optimal structure of this scaffold. To improve oral absorption, alkylation of the 1-nitrogen atom of the pyrazole ring and prodrug formation of the sugar moiety were effective; therefore, iso-Pr and ethoxycarbonyl groups were resp. introduced. The experimental part of the paper was very detailed, including the reaction process of Ethyl 3-oxopentanoate(cas: 4949-44-4Name: Ethyl 3-oxopentanoate)
Ethyl 3-oxopentanoate(cas: 4949-44-4) belongs to ketone compounds. Ketones are highly reactive, although less so than aldehydes, to which they are closely related. Much of their chemical activity results from the nature of the carbonyl group. Ketones readily undergo a wide variety of chemical reactions.Name: Ethyl 3-oxopentanoate
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