CGP-7040

Chemical Name: 3-[4-(2,4,6-Trimethylbenzyl)piperazin-1-yl]rifamycin SV
CAS No. 109006-01-1
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator)
合成路线:This compound has been obtained by two related ways:1.By direct condensation of rifamycin S (I) with 1-(2,4,6-trimethylphenyl)piperazine (II),followed by reduction of the quinone subunit to the target hydroquinone with sodium ascorbate.2.The bromination of rifamycin S (I) with Br2/pyridine in DMF gives 3-bromorifamycin S (III),which is condensed with piperazine (II) and reduced to the target hydroquinone as before.
📌 参考资料/链接:
参考文献标题:Process for the preparation of a peptide derivative of the lysergic acid
文献作者:(Novartis AG)
参考来源:CH 282603

📄 详细内容


合成路线: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).

合成路线:The cyclization of 5-ethylpiperidine-2-carboxylic acid ethyl ester (I) with aziridine (II) in ethanol gives 7-ethylperhydropyrido[1,2-a]pyrazin-1-one (III),which is reduced with LiAlH4 to yield 7-ethylperhydropyrido[1,2-a]pyrazine (IV).The reaction of (IV) with NaNO2/HCl,followed by reduction with LiAlH4,affords 7-ethylperhydropyrido[1,2-a]pyrazin-2-amine (V),which is finally condensed with rifamicin SV-3-carbaldehyde (VI).

合成路线:This compound has been obtained by two related ways:1.By direct condensation of rifamycin S (I) with 1-(2,4,6-trimethylphenyl)piperazine (II),followed by reduction of the quinone subunit to the target hydroquinone with sodium ascorbate.2.The bromination of rifamycin S (I) with Br2/pyridine in DMF gives 3-bromorifamycin S (III),which is condensed with piperazine (II) and reduced to the target hydroquinone as before.

参考文献标题:New Rifamycins
文献作者:Traxler,P.; Vischer,W.; Zak,O.
参考来源:Drugs Fut 1988,13(9),845


合成路线:This compound has been obtained by two related ways:1.By direct condensation of rifamycin S (I) with 1-(2,4,6-trimethylphenyl)piperazine (II),followed by reduction of the quinone subunit to the target hydroquinone with sodium ascorbate.2.The bromination of rifamycin S (I) with Br2/pyridine in DMF gives 3-bromorifamycin S (III),which is condensed with piperazine (II) and reduced to the target hydroquinone as before.
参考文献标题:3-Alkylbenzylpiperazinyl-rifamycins: New rifamycins with long plasma half-lives,high activity aganist Micobacterium avium complex (MAC) and reverse transcription
文献作者:Vischer,W.; Traxler,P.; Kump,W.; Costa-Pereira,R.; Gowrishankar,R.; Zak,O.; Lydon,N.; Ashtekar,D.R.; Batt,E.; Tosch,W.
参考来源:27th Intersci Conf Antimicrob Agents Chemother 1987,Abst 275