NECA, LS-143766, -Drug Synthesis Database

【结构式】

【药物名称】NECA, LS-143766

【化学名称】N5'-Ethyladenosine-5'-uronamide
　　　　　　Adenosin-5'-oic acid ethylamide

【CA登记号】84272-21-9

【分子式】C₁₂H₁₆N₆O₄

【分子量】308.29912

【开发单位】Abbott (Originator)

【药理作用】Antiplatelet Therapy, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS

合成路线1

The oxidation of 2',3'-isopropylideneadenosine (I) with potassium permanganate gives 2',3'-isopropylideneadenosine-5'-carboxylic acid (II) which with SOCl2 affords 2',3'-isopropylideneadenosine-5'-carbonyl chloride (III), which is treated first with dry liquid ethylamine and then hydrolyzed with aqueous hydrochloric acid.

参考文献中间体

【1】 Stein, H.H.; Prasad, R.N.; US 4029884 .
【2】 Stein, H.H.; Prasad, R.N.; US 3830796 .
【3】 Stein, H.H.; Prasad, R.N.; US 3914414 .
【4】 Stein, H.H.; Prasad, R.N.; US 3914415 .
【5】 Stein, H.H.; Prasad, R.N; US 3931401 .
【6】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hopkins, S.J.; NECA. Drugs Fut 1981, 6, 10, 627.
【7】 Stein, H.H.; Prasad, R.N.; US 3966917 .
【8】 Tietje, K.; Prasad, R.N.; N1,N6-Etheno-adenosine 5'-(N-ethylcarboxamide). Nucleic Acid Chemistry 1978, 2, 701-707.
【9】 Harman, R.E.; et al.; Permanganate oxidation of purine nucleosides. Chem Ind 1969, 1141.
【10】 Savic, M.; Brondyk, H.; Egan, R.S.; Bariana, D.S.; Fung, A.; Tietje, K.; Prasad, R.N.; Stein, H.H.; Modifications of the 5' position of purine nucleosides. 2. Synthesis and some cardiovascular properties of adenosine-5'-(N-substituted)carboxamides. J Med Chem 1980, 23, 3, 313-319.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	10928	Ethanamine	75-04-7	C₂H₇N	详情	详情
(I)	17560	[(3aR,4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol	362-75-4	C₁₃H₁₇N₅O₄	详情	详情
(II)	39020	(3aR,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid		C₁₃H₁₅N₅O₅	详情	详情
(III)	39021	(3aR,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl chloride		C₁₃H₁₄ClN₅O₄	详情	详情

Extended Information