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【结 构 式】

【药物名称】

【化学名称】2(S)-[4-(2-Amino-6-methyl-4-oxo-3,4-dihydroquinazolin-5-ylsulfanyl-benzamido]-2-(3-hydroxyphenyl)acetic acid

【CA登记号】

【 分 子 式 】C24H20N4O5S

【 分 子 量 】476.5148

【开发单位】Choongwae (Originator)

【药理作用】ONCOLYTIC DRUGS, Antimetabolites, Thymidylate Synthase Inhibitors

合成路线1

Strecker condensation of 3-hydroxybenzaldehyde (I) with trimethylsilyl cyanide in the presence of (S)-2-phenylglycine (II) yielded the chiral aminonitrile (III) as the major diastereoisomer. Oxidative cleavage of the chiral auxiliary of (III) with lead tetraacetate, followed by acid hydrolysis of the nitrile group provided the (S)-amino acid (IV), which was esterified with MeOH and Me3SiCl. The resulting aminoester (V) was coupled with carboxylic acid (VI) using diphenylphosphoryl azide to form amide ester (VII). Finally, saponification of the methyl ester of (VIII) afforded the target carboxylic acid.

1 Baek, D.-J.; Park, Y.-K.; Heo, H.I.; Lee, M.; Yang, Z.; Choi, M.; Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro. Bioorg Med Chem Lett 1998, 8, 23, 3287.
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) 28537 3-hydroxybenzaldehyde 100-83-4 C7H6O2 详情 详情
(II) 10973 (2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol 20989-17-7 C8H11NO 详情 详情
(III) 29636 (2S)-2-(3-hydroxyphenyl)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]ethanenitrile C16H16N2O2 详情 详情
(IV) 29637 (2S)-2-amino-2-(3-hydroxyphenyl)ethanoic acid C8H9NO3 详情 详情
(V) 29638 methyl (2S)-2-amino-2-(3-hydroxyphenyl)ethanoate C9H11NO3 详情 详情
(VI) 29639 4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoic acid C16H13N3O3S 详情 详情
(VII) 29640 methyl (2S)-2-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-(3-hydroxyphenyl)ethanoate C25H22N4O5S 详情 详情
Extended Information