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【结 构 式】 
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【药物名称】 【化学名称】8-Chloro-3-(2-propynyloxycarbonyl)pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxide 【CA登记号】 【 分 子 式 】C13H7ClN4O3 【 分 子 量 】302.67874 |
【开发单位】Università degli Studi di Firenze (Originator), Università degli Studi di Pisa (Originator) 【药理作用】Anxiolytics, PSYCHOPHARMACOLOGIC DRUGS, Drugs Acting on GABA(A) Receptors |
合成路线1
Reaction of 2-nitro-5-chlorophenylhidrazyne (I) with ethyl 2-cyano-3-ethoxypropenoate (II) in EtOH and catalytic HOAc affords derivative (III), which is simultaneously hydrolyzed and cyclized to the triazine system (IV) in aqueous NaOH. Treatment of (IV) with SOCl2 followed by addition of alcohol (V) in chloroform allows obtention of the desired product.
| 【1】 Costanzo, A.; et al.; Reactivity of 1-(2-nitrophenyl)-5-aminopyrazoles under basic conditions and synthesis of new 3,7 and 8-substituted pyrazole[5,1-c][1,2,4]benzotriazine 5-oxides, as benzodiazepine receptor ligands. J Heterocycl Chem 1994, 31, 1369. |
| 【2】 Costa, B.; Ciciani, G.; Costanzo, A.; Ipponi, A.; Martini, C.; Bruni, F.; Guerrini, G.; Selleri, S.; Lucacchini, A.; Aiello, M.; Benzodiazepine receptor (BZR) ligands.5. New 3-alkyloxycarbonyl-, 3-cyclo-alkyloxycarbonyl-, 3-aryloxy-carbonylderivatives of pyrazolo [5,1-c][1,2,4]benzotriazine 5-oxides: A study on the 3-ester function modification. Med Chem Res 1999, 9, 5, 322. |
| 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) | 35819 | 1-(5-chloro-2-nitrophenyl)hydrazine | C6H6ClN3O2 | 详情 | 详情 | |
| (II) | 43041 | ethyl (Z)-2-cyano-3-ethoxy-2-propenoate | 94-05-3 | C8H11NO3 | 详情 | 详情 |
| (III) | 43042 | ethyl 5-amino-1-(5-chloro-2-nitrophenyl)-1H-pyrazole-4-carboxylate | C12H11ClN4O4 | 详情 | 详情 | |
| (IV) | 43043 | 3-carboxy-8-chloropyrazolo[5,1-c][1,2,4]benzotriazin-5-ium-5-olate | C10H5ClN4O3 | 详情 | 详情 | |
| (V) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
Extended Information