3-[(12aR)-2-methyl-1,3,4,5,12,12a-hexahydropyrido[3,4-b]acridin-4(2H)-yl]phenyl methyl ether; (4aS,12aR)-4a-(3-methoxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octahydropyrido[3,4-b]acridine -Drug Synthesis Database

【结构式】

【分子编号】18303

【品名】3-[(12aR)-2-methyl-1,3,4,5,12,12a-hexahydropyrido[3,4-b]acridin-4(2H)-yl]phenyl methyl ether; (4aS,12aR)-4a-(3-methoxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octahydropyrido[3,4-b]acridine

【CA登记号】

【分子式】C₂₄H₂₆N₂O

【分子量】358.48332

【元素组成】C 80.41% H 7.31% N 7.81% O 4.46%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The cyclization of perhydroisoquinoline (I) with o-amino-benzaldehyde (II) in the presence of methanesulfonic acid in refluxing EtOH gave the pyridoacridine (III). Subsequent cleavage of the methyl ether function using n-PrSH and tert-BuOK in boiling DMF provided the target phenol.

参考文献中间体

合成目标

【1】 Nagase, H.; Kawai, K.; Hayakawa, J.; Wakita, H.; Mizusuna, A.; Matsuura, H.; Tajima, C.; Takezawa, Y.; Endoh, T.; Rational drug design and synthesis of a highly selective nonpeptide delt-opioid agonist, (4aS,12aR)-4a-(3-hydroxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octrahydropyrido[3,4-b]acridine (TAN-67). Chem Pharm Bull 1998, 46, 11, 1695.
【2】 Fujii, H.; et al.; Rational drug design and synthesis of opioid delta-receptor selective nonpeptidic agonists - Optical resolution of (±) TAN-67 and the pharmacological effect of each enantiomer. Symp Med Chem 1999, Abst 1P-21.

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)	18301	(4aS,8aR)-4a-(3-methoxyphenyl)-2-methyloctahydro-6(2H)-isoquinolinone		C₁₇H₂₃NO₂	详情	详情
(II)	18302	2-Aminobenzaldehyde	529-23-7	C₇H₇NO	详情	详情
(III)	18303	3-[(12aR)-2-methyl-1,3,4,5,12,12a-hexahydropyrido[3,4-b]acridin-4(2H)-yl]phenyl methyl ether; (4aS,12aR)-4a-(3-methoxyphenyl)-2-methyl-1,2,3,4,4a,5,12,12a-octahydropyrido[3,4-b]acridine		C₂₄H₂₆N₂O	详情	详情

Extended Information