|
【结 构 式】 
|
【药物名称】URB-597, LS-193379 【化学名称】N-Cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester 【CA登记号】555-55-5 【 分 子 式 】C20H22N2O3 【 分 子 量 】338.40994 |
【开发单位】Università degli Studi "La Sapienza" (Originator), Università degli Studi di Bari (Originator), Università degli Studi di Napoli (Originator), Università degli Studi di Parma (Originator), Università degli Studi di Urbino (Originator), University of Calif 【药理作用】Anxiolytics, PSYCHOPHARMACOLOGIC DRUGS, Fatty Acid Amide Hydrolase (FAAH) Inhibitors |
合成路线1
Hydrolysis of 3-bromobenzonitrile (I) by means of sodium perborate leads to amide (II). Subsequent Suzuki coupling of 3-bromobenzamide (II) with 3-methoxyphenylboronic acid (III) furnishes the biphenyl compound (IV). The methyl ether group of (IV) is then cleaved employing BBr3 to yield phenol (V). This is finally coupled with cyclohexyl isocyanate (VI) to produce the title carbamate.
| 【1】 Kathuria, S.; Gaetani, S.; Fegley, D.; Valiño, M.; Duranti, A.; Tontini, A.; Mor, M.; Tarzia, G.; La Rana, G.; Calignano, A.; Giustino, A.; Tattoli, M.; Palmery, M.; Cuomo, V.; Piomelli, D.; Modulation of anxiety through blockade of anandamide hydrolysis. Nat Med 2003, 9, 1, 76. |
| 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) | 26573 | 3-bromobenzonitrile | 6952-59-6 | C7H4BrN | 详情 | 详情 |
| (II) | 63206 | 3-bromobenzamide | C7H6BrNO | 详情 | 详情 | |
| (III) | 29426 | 3-methoxyphenylboronic acid | 10365-98-7 | C7H9BO3 | 详情 | 详情 |
| (IV) | 63207 | 3'-methoxy[1,1'-biphenyl]-3-carboxamide | C14H13NO2 | 详情 | 详情 | |
| (V) | 63208 | 3'-hydroxy[1,1'-biphenyl]-3-carboxamide | C13H11NO2 | 详情 | 详情 | |
| (VI) | 18108 | 1-isocyanatocyclohexane; cyclohexyl isocyanate | 3173-53-3 | C7H11NO | 详情 | 详情 |