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【结 构 式】 
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【药物名称】NSC-350386(hydrochloride hydrate), NSC-370147 【化学名称】5-Amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazin-7-ylcarbamic acid ethyl ester 2-hydroxyethylsulfonate hydrate 【CA登记号】83269-10-7 (free base) 【 分 子 式 】C19H27N5O7S 【 分 子 量 】469.52034 |
【开发单位】Pfizer (Originator), Southern Research Institute (Originator) 【药理作用】ONCOLYTIC DRUGS |
合成路线1
A number of 1-deaza-7,8-dihydropteridines with antimitotic activity have been prepared by the route shown in the scheme for NSC-350386 (1,2). Reaction of 2-aminopropiophenone oxime with ethyl 6-amino-4-chloro-5-nitropyridin-2-ylcarbamate (I) gave (II), which was hydrolyzed in a mixture of dioxane and hydrochloric acid to give the ketone (III). Reductive cyclization of (III) was effected with Raney Nickel and hydrogen.
| 【1】 Wheeler, G.P.; Temple, C. Jr.; NSC-350386. Drugs Fut 1983, 8, 11, 927. |
| 【2】 Rose, J.D.; Kussner, C.L.; Temple, C. Jr.; Wheeler, G.P.; Comber, R.N.; Montgomery, J.A.; Elliot, R.D.; New anticancer agents agents: Synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines). J Med Chem 1982, 25, 9, 1045. |
| 【3】 Temple, C. Jr.; et al.; 1,2-Dihydropyrido[3,4-b]pyrazines: Structure-activity relationships. J Med Chem 1983, 26, 1, 91. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 36134 | 2-amino-1-phenyl-1-propanone oxime | C9H12N2O | 详情 | 详情 | |
| (I) | 13354 | ethyl 6-amino-4-chloro-5-nitro-2-pyridinylcarbamate | C8H9ClN4O4 | 详情 | 详情 | |
| (II) | 36135 | ethyl 6-amino-4-[[2-(hydroxyimino)-1-methyl-2-phenylethyl]amino]-5-nitro-2-pyridinylcarbamate | C17H20N6O5 | 详情 | 详情 | |
| (III) | 13357 | ethyl 6-amino-4-[[(1S)-1-methyl-2-oxo-2-phenylethyl]amino]-5-nitro-2-pyridinylcarbamate | C17H19N5O5 | 详情 | 详情 |