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【结 构 式】

【分子编号】33698

【品名】3-[([1-[(1-[[(3-hydroxypropyl)(methyl)amino]methyl]cyclohexyl)disulfanyl]cyclohexyl]methyl)(methyl)amino]-1-propanol

【CA登记号】

【 分 子 式 】C22H44N2O2S2

【 分 子 量 】432.73564

【元素组成】C 61.06% H 10.25% N 6.47% O 7.39% S 14.82%

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:(VI)

Treatment of cyclohexanecarboxaldehyde (I) with sulfur monochloride produced the dimeric disulfide (II). After condensation of (II) with 3-amino-1-propanol (III), reduction with NaBH4 afforded diamine (IV). Subsequent N-methylation of (IV) to give (VI) was achieved by condensation with formaldehyde, followed by NaBH4 reduction of the resulting oxazine (V). Reductive cleavage of the disulfide group of (VI) using LiAlH4 provided thiol (VII). Optionally, nitrosation of the sulfhydryl group of (VII) by means of tert-butyl nitrite gave rise to the nitrosothio derivative (VIII). Further coupling of this compound with diclofenac (IX) in the presence of DCC and DMAP furnished the title ester. Alternatively, the title compound was prepared by esterification of mercapto alcohol (VII) with diclofenac, followed by S-nitrosation of the resulting ester (X).

1 Bandarage, U.K.; et al.; Nitrosothiol esters of diclofonecac: Synthesis and pharmacological characterization as gastrointestinal-sparing prodrugs. J Med Chem 2000, 43, 21, 4005.
2 Bandarage, U.K.; et al.; NMI-377, a nitric oxide-donating diclofenac derivative with gastroprotective properties. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 81.
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) 33694 cyclohexanecarbaldehyde 2043-61-0 C7H12O 详情 详情
(II) 33695 1-[(1-formylcyclohexyl)disulfanyl]cyclohexanecarbaldehyde C14H22O2S2 详情 详情
(III) 18522 3-amino-1-propanol 156-87-6 C3H9NO 详情 详情
(IV) 33696 3-[([1-[(1-[[(3-hydroxypropyl)amino]methyl]cyclohexyl)disulfanyl]cyclohexyl]methyl)amino]-1-propanol C20H40N2O2S2 详情 详情
(V) 33697 bis[1-(1,3-oxazinan-3-ylmethyl)cyclohexyl] disulfide; 3-[(1-[[1-(1,3-oxazinan-3-ylmethyl)cyclohexyl]disulfanyl]cyclohexyl)methyl]-1,3-oxazinane C22H40N2O2S2 详情 详情
(VI) 33698 3-[([1-[(1-[[(3-hydroxypropyl)(methyl)amino]methyl]cyclohexyl)disulfanyl]cyclohexyl]methyl)(methyl)amino]-1-propanol C22H44N2O2S2 详情 详情
(VII) 33699 3-[methyl[(1-sulfanylcyclohexyl)methyl]amino]-1-propanol C11H23NOS 详情 详情
(VIII) 33700 1-[[(3-hydroxypropyl)(methyl)amino]methyl]-N-oxocyclohexanesulfenamide C11H22N2O2S 详情 详情
(IX) 33701 Diclofenac; 2-[2-(2,6-Dichloroanilino)phenyl]acetic acid C14H11Cl2NO2 详情 详情
(X) 33702 3-[methyl[(1-sulfanylcyclohexyl)methyl]amino]propyl 2-[2-(2,6-dichloroanilino)phenyl]acetate C25H32Cl2N2O2S 详情 详情
Extended Information