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【结 构 式】 
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【药物名称】SCA-40 【化学名称】6-Bromo-8-(methylamino)imidazo[1,2-a]pyrazine-2-carbonitrile 【CA登记号】142744-39-6 【 分 子 式 】C8H6BrN5 【 分 子 量 】252.07452 |
【开发单位】CNRS (Originator) 【药理作用】Asthma Therapy, Bronchodilators, RESPIRATORY DRUGS, Phosphodiesterase III Inhibitors, Phosphodiesterase IV Inhibitors, Potassium Channel Activators |
合成路线1
The precursor imidazopyrazine (III) was prepared by condensation of 2-amino-3,5-dibromopyrazine (I) with ethyl 3-bromopyruvate (II). Subsequent treatment of ester (III) with aqueous ammonia produced the corresponding amide (IV). This was then dehydrated with phosphoryl chloride, with concomitant displacement of the 8-bromine for a chloro group, to yield nitrile (V). Finally, substitution of the chloride by methyl amine in (V) furnished the target compound.
| 【1】 Sablayrolles, C.; et al.; Synthesis of imidazo[1,2-a]pyrazine derivatives with uterine-relaxing, antibronchospastic, and cardiac-stimulating properties. J Med Chem 1984, 27, 2, 206. |
| 【2】 Vitse, O.; Laurent, F.; Pocock, T.M.; et al.; New imidazol[1,2-a]pyrazine derivatives withbronchodilatory and cyclic nucleotide phosphodiesterase inhibitory activities. Bioorg Med Chem 1999, 7, 6, 1059. |
| 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) | 26178 | 3,5-dibromo-2-pyrazinamine | 24241-18-7 | C4H3Br2N3 | 详情 | 详情 |
| (II) | 25183 | ethyl 3-bromo-2-oxopropanoate;ethyl 3-bromopyruvate;Bromopyruvic acid ethyl ester;ethyl 3-bromopyruvate;ethyl bromopyruvate | 70-23-5 | C5H7BrO3 | 详情 | 详情 |
| (III) | 26179 | ethyl 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxylate | C9H7Br2N3O2 | 详情 | 详情 | |
| (IV) | 26180 | 6,8-dibromoimidazo[1,2-a]pyrazine-2-carboxamide | C7H4Br2N4O | 详情 | 详情 | |
| (V) | 26181 | 6-bromo-8-chloroimidazo[1,2-a]pyrazine-2-carbonitrile | C7H2BrClN4 | 详情 | 详情 |