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【结 构 式】 
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【药物名称】PD-160678 【化学名称】N-[4-(3-Bromophenylamino)-7-quinazolinyl]-2-propenamide 【CA登记号】 【 分 子 式 】C17H13BrN4O 【 分 子 量 】369.22336 |
【开发单位】Warner-Lambert 【药理作用】ONCOLYTIC DRUGS, INHIBITORS OF SIGNAL TRANSDUCTION PATHWAYS |
合成路线1
Coupling of chloroquinazoline (I) with 3-bromoaniline (II) in refluxing isopropanol yielded anilinoquinazoline (III). The nitro group was then reduced with Fe dust and AcOH in aqueous ethanol to give amine (IV). Finally, condensation with acrylic acid (V) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF provided the target acrylamide.
| 【1】 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth f. J Med Chem 1995, 38, 18, 3482. |
| 【2】 Dobrusin, E.M.; Bridges, A.J.; Zhou, H.; Smaill, J.B.; Doherty, A.M.; Denny, W.A.; McNamara, D.J.; Showalter, H.D. (Pfizer Inc.); Irreversible inhibitors of tyrosine kinases. JP 2000508657; WO 9738983 . |
| 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) | 19135 | 4-chloro-7-nitroquinazoline | C8H4ClN3O2 | 详情 | 详情 | |
| (II) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (III) | 19137 | N-(3-bromophenyl)-N-(7-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-7-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (IV) | 19138 | N(4)-(3-bromophenyl)-4,7-quinazolinediamine; N-(7-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 | |
| (V) | 19139 | acrylic acid | 79-10-7 | C3H4O2 | 详情 | 详情 |
Extended Information