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【结 构 式】

【药物名称】Antineoplaston AS2-5

【化学名称】N2-Phenylacetyl-L-glutamine sodium salt

【CA登记号】104771-87-1, 28047-15-6 (free acid), 31427-44-8 (free acid)

【 分 子 式 】C13H15N2NaO4

【 分 子 量 】286.2653

【开发单位】Burzynski Research Institute (Originator), National Cancer Institute (Not Determined)

【药理作用】Oncolytic Drugs, Prostate Cancer Therapy

合成路线1

Antineoplaston AS2-5 (AS2-5) can be obtained in the following way (1,2): N-Phenylacetyl-L-glutamine sodium is synthesized in two steps. In the first step, phenylacetic acid (I) is treated with N-hydroxysuccinimide (B) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (A) in acetonitrile to give intermediate (Ia). In the second step, (Ia) is reacted without purification with L-glutamine (II) in the presence of NaHCO3 in 1:1 acetonitrile-water mixture to afford N-phenylacetyl-L-glutamine (III) in 87% yield. Compound (III) is then converted to sodium salt in aqueous solution by treatment with aqueous sodium hydroxide solution (pH 7). In a large scale preparation reaction of phenylacetyl chloride with L-glutamine in aqueous solution containing NaHCO3 affords N-phenyiacetyl L-glutamine sodium.

1 Burzynski, S.R. (Burzynski Research Institute); Purified antineoplaston fractions and methods of treating neoplastic disease. US 4558057 .
2 Berman, E.M.; Gregor, V.E.; Showalter, H.H.D. (Pfizer Inc.); Benzoselenino[4,3,2-cd]indazole compound, compositions comprising the compounds and processes for producing the compounds. AU 8544154; EP 0170412; ES 8704956 .
3 Khalid, M.; Burzynski, S.R.; Antineoplaston AS2-5. Drugs Fut 1986, 11, 5, 364.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10264 1-Hydroxydihydro-1H-pyrrole-2,5-dione; N-Hydroxysuccinimide; 1-Hydroxy-2,5-pyrrolidinedione 6066-82-6 C4H5NO3 详情 详情
(Ia) 24927 tert-butyl (2R,3aR,7aR,10aR)-8-(dimethoxymethyl)-5-(5-hexenyl)-10-oxo-2-vinyl-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2,3-i]isoquinoline-1(4H)-carboxylate C27H42N2O5 详情 详情
(A) 24945 N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide 25952-53-8 C8H17N3 详情 详情
(I) 16148 Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid 103-82-2 C8H8O2 详情 详情
(II) 24948 L-glutamine 56-85-9 C5H10N2O3 详情 详情
(III) 24949 (2S)-5-amino-5-oxo-2-[(2-phenylacetyl)amino]pentanoic acid C13H16N2O4 详情 详情
Extended Information