ST-1420
Chemical Name: 3(R)-(Dodecylsulfonamido)-4-(trimethylammonium)butyrate
CAS No. 250694-19-0, 250694-18-9 (enantiomer)
项目整合开发状态: Preclinical
项目研究机构: Sigma-Tau (Originator)
合成路线:Pentadecanoyl chloride (I) is treated with NaN3 to form the corresponding acyl azide (II),which undergoes Curtius rearrangement to isocyanate (III) upon heating in toluene.Coupling of isocyanate (III) with aminocarnitine (IV) then produces the title urea derivative.
合成路线:(R)-Aminocarnitine (I) was esterified with HCl in refluxing isobutanol to afford the isobutyl ester (II).Acylation of amino ester (II) with dodecanesulfonyl chloride (III) in the presence of triethylamine provided the corresponding sulfonamide (IV).The title compound was then obtained by basic hydrolysis of the isobutyl ester group of (IV).
📌 参考资料/链接：
参考文献标题:Cpds.having reversible inhibiting activity of carnitine palmitoyl-transferase
文献作者:Marzi,M.; Tinti,M.O.; Giannessi,F.; Minetti,P.; De Angelis,F.; Chiodi,P.; Arduini,A.(Sigma-Tau Industrie Farmaceutiche Riunite SpA)
参考来源:EP 1077925; US 6369073; WO 9959957
📄 详细内容
合成路线:(R)-Aminocarnitine (I) was esterified with HCl in refluxing isobutanol to afford the isobutyl ester (II).Acylation of amino ester (II) with dodecanesulfonyl chloride (III) in the presence of triethylamine provided the corresponding sulfonamide (IV).The title compound was then obtained by basic hydrolysis of the isobutyl ester group of (IV).
参考文献标题:Reversible carnitine palmitoyltransferase inhibitors with broad chemical diversity as potential antidiabetic agents
文献作者:Giannessi,F.; Chiodi,P.; Marzi,M.; Minetti,P.; Pessotto,P.; De Angelis,F.; Tassoni,E.; Conti,R.; Giorgi,F.; Mabilia,M.; Dell'Uomo,N.; Muck,S.; Tinti,M.O.; Carminati,P.; Arduini,A.
参考来源:J Med Chem 2001,44(15),2383