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【结 构 式】 
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【药物名称】SIM-01 【化学名称】5,15-Bis(3,5-dihydroxyphenyl)-7,8,21,23-tetrahydroporphine 【CA登记号】394661-77-9 【 分 子 式 】C32H24N4O4 【 分 子 量 】528.57248 |
【开发单位】CHU Nantes (Originator) 【药理作用】ONCOLYTIC DRUGS, Photosensitizers, Radiation Therapy |
合成路线1
Acid-catalyzed condensation of dipyrrolylmethane (I) with 3,5-dimethoxybenzaldehyde (II) gives rise to the porphyrin derivative (III). Subsequent demethylation of the methoxy groups of (III) employing BBr3 affords the tetraphenol compound (IV). Finally, partial reduction of (IV) by means of p-toluenesulfonyl hydrazide in hot pyridine furnishes the title compound (1,2).
| 【1】 Bourré, L.; Simmoneaux, G.; Ferrand, Y.; Thibaut, S.; Lajat, Y.; Patrice, T.; Synthesis, and in vitro and in vivo evaluation of a diphenylchlorin sensitizer for photodynamic therapy. J Photochem Photobiol B Biol 2003, 69, 3, 179. |
| 【2】 Bourre, L.; Patrice, T.; Dihydroporphyrin derivs. and their uses. EP 1305317; FR 2812637; US 2004022734; WO 0210173 . |
| 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) | 64350 | 2-(1H-pyrrol-2-ylmethyl)-1H-pyrrole | C9H10N2 | 详情 | 详情 | |
| (II) | 21720 | 3,5-dimethoxybenzaldehyde | 7311-34-4 | C9H10O3 | 详情 | 详情 |
| (III) | 64351 | 3-[12-[3,5-bis(methyloxy)phenyl]-21,22,23,24-tetraazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3(24),4,6,8,10,12,14,16(22),17,19-undecaen-2-yl]-5-(methyloxy)phenyl methyl ether; 2,12-bis[3,5-bis(methyloxy)phenyl]-21,22,23,24-tetraazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaene | C36H30N4O4 | 详情 | 详情 | |
| (IV) | 64352 | 5-[12-(3,5-dihydroxyphenyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1~3,6~.1~8,11~.1~13,16~]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-2-yl]-1,3-benzenediol | C32H22N4O4 | 详情 | 详情 |
Extended Information