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【结 构 式】 
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【药物名称】 【化学名称】5-[(1aS,8S,8aR,8bS)-6-Amino-8-(carbamoyloxymethyl)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-1-yl]-5-oxopentanoic acid 9-fluoro-11beta-hydroxy-16alpha,17-(isopropylidenedioxy)-3,20-dioxopregna-1,4-dien-21-yl ester 【CA登记号】 【 分 子 式 】C44H53FN4O13 【 分 子 量 】864.93041 |
【开发单位】Medical University of South Carolina (Originator) 【药理作用】Chemical Delivery Systems, DRUG DELIVERY, Drug Delivery Systems, OCULAR MEDICATIONS, ONCOLYTIC DRUGS, Ophthalmic Drugs, Apoptosis Inducers, Glucocorticoids |
合成路线1
The reaction of triamcinolone (I) with acetone and HCl gives the corresponding acetonide (II), which is condensed with glutaric anhydride (III) in pyridine to yield the glutaric monoester (IV). Finally, this compound is condensed with mitomycin C (V) by means of CDI in THF to afford the target conjugate.
| 【1】 Crosson, C.E.; Künzel, E.; Heredia, M.L.; Rix, U.; Oelkers, C.; Rohr, J.; Rohrer, B.; Winberly, M.; Macky, T.A.; Synthesis, pharmacokinetics, efficacy, and rat retinal toxicity of a novel mitomycin C-triamcinolone acetonide conjugate. J Med Chem 2002, 45, 5, 1122. |
| 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) | 39959 | (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-17-glycoloyl-11,16,17-trihydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | 124-94-7 | C21H27FO6 | 详情 | 详情 |
| (II) | 53587 | 5-{2-[(4aS,4bR,5S,6aS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6-yl]-2-oxoethoxy}-5-oxopentanoic acid | n/a | C29H37FO9 | 详情 | 详情 |
| (III) | 15512 | Glutaric Anhydride; dihydro-2H-pyran-2,6(3H)-dione | 108-55-4 | C5H6O3 | 详情 | 详情 |
| (IV) | 53588 | [(1aS,8S,8aR,8bS)-6-amino-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate | n/a | C15H18N4O5 | 详情 | 详情 |
| (V) | 53589 | 2-Nitro-p-phenetidine; 4-Amino-3-nitrophenetole; 4-Ethoxy-2-nitroaniline; 4-Ethoxy-2-nitrobenzeneamine | 616-86-4 | C8H10N2O3 | 详情 | 详情 |