【药物名称】
化学结构式(Chemical Structure):
参考文献No.536228
标题:Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT1A receptor antagonists
作者:Yasunaga, T.; Kimura, T.; Naito, R.; Kontani, T.; Wanibuchi, F.; Yamashita, H.; Nomura, T.; Tsukamoto, S.; Yamaguchi, T.; Mase, T.
来源:J Med Chem 1998,41(15),2765
合成路线图解说明:

6-Fluoro-8-hydroxychroman-4-one (I) was converted to ethylene ketal (II) upon treatment with ethylene glycol and triethyl orthoformate, and subsequently alkylated with 1,2-dibromoethane under phase-transfer conditions to afford the bromoethyl ether (III). Wittig condensation of piperonal (V) with the (3-phthalimidopropyl)phosphonium salt (IV) in the presence of NaOMe in dioxan provided olefin (VI), which was hydrogenated over Pd/C to furnish the arylbutyl phthalimide (VII). Further deprotection of the phthalimido group of (VII) with CH3NH2 gave amine (VIII). Then, alkylation of (VIII) with bromide (III), followed by acid hydrolysis of the ketal function yielded the title compound.

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