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【结 构 式】 
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【药物名称】N276-26 【化学名称】4-(2,2-Diphenylethyl)-2-methyl-6-[4-(2-isopropyl-1H-imidazo[4,5-c]pyridin-1-yl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid 5-ethyl 3-[3-(3-pyridinyl)prop-2-ynyl] diester 【CA登记号】235417-40-0 【 分 子 式 】C47H43N5O4 【 分 子 量 】741.89786 |
【开发单位】Nikken Chemicals (Originator) 【药理作用】Modulators of the Therapeutic Activity of Antineoplastic Agents, Multidrug Resistance Modulators, ONCOLYTIC DRUGS |
合成路线1
Palladium-catalyzed coupling of 3-bromopyridine (I) with propargyl alcohol (II) produced 3-(3-pyridyl)propargyl alcohol (III). Reaction of alcohol (III) with diketene (IV) in the presence of DMAP gave the acetoacetate ester (V), which was subsequently treated with ammonia in THF to furnish the enamino ester (VI). The title dihydropyridine derivative was then obtained by Hantzsch's synthesis upon condensation between ethyl 4-(2-isopropylimidazo[4,5-c]pyridin-1-yl)benzoylacetate (VII), enamino ester (VI) and 3,3-diphenylpropanal in refluxing EtOH.
| 【1】 Tasaka, S.; Omori, H.; Tanabe, H.; Gomi, N.; Kiue, A. (Nikken Chemicals Co., Ltd.); 1,4-Dihydropyridine derivs.. EP 1055672; JP 2000044559; US 6306853; WO 9941250 . |
| 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) | 13255 | methyl 3-[((1R,2E,4Z)-1-[(S)-hydroxy[3-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]-2,4-tetradecadienyl)sulfanyl]propanoate | C45H52N4O3S | 详情 | 详情 | |
| (II) | 16664 | Propargyl Alcohol; 2-propyn-1-ol | 107-19-7 | C3H4O | 详情 | 详情 |
| (III) | 48612 | 3-(3-pyridinyl)-2-propyn-1-ol | C8H7NO | 详情 | 详情 | |
| (IV) | 11367 | 4-Methylene-2-oxetanone; Acetyl ketene | 674-82-8 | C4H4O2 | 详情 | 详情 |
| (V) | 48613 | 3-(3-pyridinyl)-2-propynyl 3-oxobutanoate | C12H11NO3 | 详情 | 详情 | |
| (VI) | 48614 | 3-(3-pyridinyl)-2-propynyl (E)-3-amino-2-butenoate | C12H12N2O2 | 详情 | 详情 | |
| (VII) | 48615 | ethyl 3-[4-(2-isopropyl-1H-imidazo[4,5-c]pyridin-1-yl)phenyl]-3-oxopropanoate | C20H21N3O3 | 详情 | 详情 |