CGP-27557, -Drug Synthesis Database

【结构式】

【药物名称】CGP-27557

【化学名称】3-(1-Iminomethyl-1,4-diazabicyclo[4.4.0]decyl)rifamycin SV
　　　　　　21-Acetoxy-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20-22-heptamethyl-8-(octahydropyrido[1,2-a]pyrazin-2-yliminomethyl)-2,7-(epoxypentadeca-1,11,13-trienimino)naphtho[2,1-b]furan-1,11-dione

【CA登记号】100070-77-7

【分子式】C₄₆H₆₂N₄O₁₂

【分子量】863.02664

【开发单位】Novartis (Originator)

【药理作用】Rifamycins

合成路线1

The cyclization of piperidine-2-carboxylic acid ethyl ester (I) with aziridine (II) in ethanol gives perhydropyrido[1,2-a]pyrazin-1-one (III), which is reduced with LiAlH4 to yield perhydropyrido[1,2-a]pyrazine (IV). The reaction of (IV) with NaNO2/HCl, followed by reduction with LiAlH4, affords perhydropyrido[1,2-a]pyrazin-2-amine (V), which is finally condensed with rifamicin SV-3-carbaldehyde (VI).

参考文献中间体

【1】 Hauffe, S.; Tosch, W.; Batt, E.; Ashtekar, D.R.; Costa-Pereira, R.; Vischer, W.; Traxler, P.; Degen, P.; Zak, O.; Imhof, P.; Gowrishankar, R.; 3-Formylrifamycin SV-hydrazones with diazabicycloalkyl side-chains: New rifamycins aganist tuberculosis with long plasma half-lives. 27th Intersci Conf Antimicrob Agents Chemother 1987, Abst 278.
【2】 Ashtekar, D.R.; Vischer, W.; Kump, W.; Costa-Pereira, R.; Traxler, P.; Subrahmanyam, D.; Gowrishankar, R.; Antitubercular activity in vitro and in vivo of new long-acting rifamycin derivatives. Bull Intl Union Tuberc 1986, 61, 3, 8.
【3】 Traxler, P. (Novartis Corp.); Novel polycyclic hydrazones of rifamycins, their manufacture, and their pharmaceutical compsns. for treating tuberculosis. US 4681938 .
【4】 Traxler, P.; Vischer, W.; Zak, O.; New Rifamycins. Drugs Fut 1988, 13, 9, 845.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	43693	ethyl 2-piperidinecarboxylate	15862-72-3	C₈H₁₅NO₂	详情	详情
(II)	10151	Ethyleneimine; Aziridine; Azirane	151-56-4	C₂H₅N	详情	详情
(III)	43694	hexahydro-2H-pyrido[1,2-a]pyrazin-1(6H)-one		C₈H₁₄N₂O	详情	详情
(IV)	43695	octahydro-2H-pyrido[1,2-a]pyrazine		C₈H₁₆N₂	详情	详情
(V)	43696	octahydro-2H-pyrido[1,2-a]pyrazin-2-ylamine; octahydro-2H-pyrido[1,2-a]pyrazin-2-amine		C₈H₁₇N₃	详情	详情
(VI)	43692	26-formyl-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1(4,7).0(5,28)]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate		C₃₈H₄₇NO₁₃	详情	详情

Extended Information