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【结 构 式】 
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【药物名称】 【化学名称】N-[3-(7-Chloroquinolin-4-ylamino)-5-(morpholin-4-ylmethyl)phenyl]-2-(1-piperidinyl)acetamide 【CA登记号】 【 分 子 式 】C27H32ClN5O2 【 分 子 量 】494.04139 |
【开发单位】CNRS (Originator), Tibotec-Virco (Originator) 【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases |
合成路线1
The intermediate anilinoquinoline (III) was obtained by nucleophilic substitution of 4,7-dichloroquinoline (II) with 3,5-diaminobenzyl alcohol (I) in the presence of N-methylmorpholine. Coupling of (III) with chloroacetic acid gave the corresponding chloroacetamide (IV), which was further reacted with piperidine in DMF, yielding the piperidino acetamide (V). The benzyl alcohol function of (V) was then oxidized to aldehyde (VI) employing manganese dioxide. Finally, reductive condensation of aldehyde (VI) with morpholine in the presence of NaBH(OAc)3 furnished the title compound.
| 【1】 Delareu, S.; et al.; Synthesis and in vitro and in vivo antimalarial activity of new 4-anilinoquinolines. J Med Chem 2001, 44, 17, 2827. |
| 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) | 51039 | (3,5-diaminophenyl)methanol | C7H10N2O | 详情 | 详情 | |
| (II) | 38277 | 4,7-dichloroquinoline | 86-98-6 | C9H5Cl2N | 详情 | 详情 |
| (III) | 51040 | [3-amino-5-[(7-chloro-4-quinolinyl)amino]phenyl]methanol | C16H14ClN3O | 详情 | 详情 | |
| (IV) | 51041 | 2-chloro-N-[3-[(7-chloro-4-quinolinyl)amino]-5-(hydroxymethyl)phenyl]acetamide | C18H15Cl2N3O2 | 详情 | 详情 | |
| (V) | 51042 | N-[3-[(7-chloro-4-quinolinyl)amino]-5-(hydroxymethyl)phenyl]-2-(1-piperidinyl)acetamide | C23H25ClN4O2 | 详情 | 详情 | |
| (VI) | 51043 | N-[3-[(7-chloro-4-quinolinyl)amino]-5-formylphenyl]-2-(1-piperidinyl)acetamide | C23H23ClN4O2 | 详情 | 详情 |