(+)-Hemipalmitoylcarnitinium, Z-15
Chemical Name: 2-[6(S)-Hydroxy-4,4-dimethyl-6-pentadecylmorpholinium-2(R)-yl]acetate; (2S,6R)-6-(Carboxymethyl)-2-hydroxy-4,4-dimethyl-2-pentadecylmorpholinium inner salt
CAS No. 145554-73-0, 145631-91-0 (hydrate)
项目整合开发状态: Preclinical
项目研究机构: Virginia Tech (Originator)
合成路线:Intermediate hydroxyester (III) has been obtained as follows: Demethylation of (R)-carnitine (I) by thiophenol in dimethylaminoethanol,followed by precipitation with LiOH,gave lithium carboxylate (II),which was esterified to (III) by treatment either with H2SO4 in MeOH or with trimethyl orthoformate in refluxing methanol.
合成路线:In a different procedure,treatment of olefin (VII) with N-bromosuccinimide produced bromohydrin (VIII),which was further oxidized to bromoketone (VI) by means of Jones reagent.Condensation of bromoketone (VI) with aminoalcohol (III) in nitromethane furnished the morpholine derivative (IX).The ester group was finally hydrolyzed with to yield the title compound.
📌 参考资料/链接：
参考文献标题:Acylcarnitine analogues as topical,microbicidal spermicides
文献作者:Savle,P.S.; Doncel,G.F.; Bryant,S.D.; Hubieki,M.P.; Robinette,R.G.; Gandourk,R.D.
参考来源:Bioorg Med Chem Lett 1999,9(17),2545
📄 详细内容
合成路线:The condensation of palmitoyl chloride (IV) with diazomethane produced diazoketone (V).This was then treated with HBr to yield bromoketone (VI).
合成路线:In a different procedure,treatment of olefin (VII) with N-bromosuccinimide produced bromohydrin (VIII),which was further oxidized to bromoketone (VI) by means of Jones reagent.Condensation of bromoketone (VI) with aminoalcohol (III) in nitromethane furnished the morpholine derivative (IX).The ester group was finally hydrolyzed with to yield the title compound.
参考文献标题:(+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransfease-I in intact mitochondria
文献作者:Gandour,R.D.; Leung,O.T.; Greway,A.T.; Ramsay,R.R.; Nic a'Bhaird,N.; Fronczek,F.R.; Bellard,B.M.; Kumaravel,G.
参考来源:J Med Chem 1993,36(2),237