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【结 构 式】

【药物名称】A-317920

【化学名称】N-[2-[4-[3-[4-(Cyclopropylcarbonyl)phenoxy]propyl]piperazin-1-yl]-1(R)-methyl-2-oxoethyl]furan-2-carboxamide

【CA登记号】360551-59-3

【 分 子 式 】C25H31N3O5

【 分 子 量 】453.54292

【开发单位】Abbott (Originator)

【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, Histamine H3 Receptor Antagonists

合成路线1

Intramolecular cyclization of p-hydroxy-4-chlorobutyrophenone (I) under alkaline conditions yields cyclopropyl(4-hydroxyphenyl) ketone (II). The phenolic hydroxyl group is then alkylated by 1-bromo-3-chloropropane (III) to furnish the chloropropyl ether (IV). Subsequent condensation of alkyl chloride (IV) with piperazine (V) gives rise to the N-substituted piperazine (VI). This is then coupled with N-Boc-L-alanine (VII) in the presence of EDC/DMAP to afford amide (VIII) (1, 2). After acidic cleavage of the N-Boc protecting group, the resultant monosubstituted piperazine (IX) is acylated by furanoyl chloride (X) to furnish the target furamide derivative

1 Black, L.A.; Faghih, R.; Liu, H.; et al.; Acyl-D-alanine amides: Selective histamine H3 receptor antagonists. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 323.
2 Black, L.A.; Faghih, R.; Bennani, Y.L.; Liu, H.; Zhang, H.Q.; Dwight, W.J.; Gentles, R.G.; Phelan, K.M.; Vasudevan, A. (Abbott Laboratories Inc.); Cyclic and bicyclic diamino histamine-3 receptor antagonists. WO 0166534 .
3 Black, L.A.; Faghih, R.; Bennani, Y.L.; Liu, H.; Zhang, H.Q.; Dwight, W.J.; Gentles, R.G.; Phelan, K.M.; Vasudevan, A. (Abbott Laboratories Inc.); Cyclic and bicyclic diamino histamine-3 receptor antagonists. US 2001049367; US 6559140 .
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) 62995   C10H11ClO2 详情 详情
(II) 27425 cyclopropyl(4-hydroxyphenyl)methanone C10H10O2 详情 详情
(III) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(IV) 62988 5-bromo-N-(1H-imidazol-2-yl)-6-quinoxalinamine; N-(5-bromo-6-quinoxalinyl)-N-(1H-imidazol-2-yl)amine C11H8BrN5 详情 详情
(V) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
(VI) 62996   C17H24N2O2 详情 详情
(VII) 15859 Boc-D-Alanine; (2R)-2-[(tert-butoxycarbonyl)amino]propionic acid 7764-95-6 C8H15NO4 详情 详情
(VIII) 63042   C28H23ClN2O2 详情 详情
(IX) 63043   C17H15ClN2O2 详情 详情
(X) 26093 2-Furoyl chloride 527-69-5 C5H3ClO2 详情 详情
Extended Information