|
【结 构 式】 
|
【药物名称】Azacrown-TEPA, LS-148956 【化学名称】13-[Bis(1-aziridinyl)phosphoryl]-1,4,7,10-tetraoxa-13-azacyclopentadecane 【CA登记号】101347-44-8 【 分 子 式 】C14H28N3O5P 【 分 子 量 】349.37016 |
【开发单位】 【药理作用】ONCOLYTIC DRUGS |
合成路线1
Title compound can be prepared by two different ways: 1) The reaction of 1,4,7,10-tetraoxa-13-azacyclopentandecane (I) with phosphoryl chloride in the presence of triethylamine in diethyl ether gives 13-(dichlorophosphoryl)-1,4,7,10-tetraoxa-13-azacyclopentandecane (II), which is subsequently reacted with aziridine (III) in the presence of triethylamine to give azacrown-TEPA. 2) The reaction of the aziridine (III) with phosphoryl chloride in the presence of triethylamine in diethyl ether gives bis(1-aziridinyl)chlorophosphine oxide (IV), which is subsequently reacted with 1,4,7,10-tetraoxa-13-azacyclopentandecane (I) in the presence of triethylamine to afford azacrown-TEPA.
| 【1】 Okahara, M.; Nakatsuji, Y.; Maeda, H.; Facile synthesis of monoaza crown ethers. J Med Chem 1981, II, 471-472. |
| 【2】 Lukszo, J.; Sosnovsky, G.; Azacrown-TEPA. Drugs Fut 1985, 10, 4, 275. |
| 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) | 29102 | 1,4,7,10-tetraoxa-13-azacyclopentadecane | 66943-05-3 | C10H21NO4 | 详情 | 详情 |
| (II) | 29103 | 1,4,7,10-tetraoxa-13-azacyclopentadecan-13-ylphosphonic dichloride | C10H20Cl2NO5P | 详情 | 详情 | |
| (III) | 10151 | Ethyleneimine; Aziridine; Azirane | 151-56-4 | C2H5N | 详情 | 详情 |
| (IV) | 29104 | di(1-aziridinyl)phosphinic chloride | C4H8ClN2OP | 详情 | 详情 |