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【结 构 式】 
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【分子编号】25488 【品名】(3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-(acetamido)hexanoyl]amino]-12-([1-[(benzyloxy)methyl]-1H-imidazol-5-yl]methyl)-3-[(1-formyl-1H-indol-3-yl)methyl]-6-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-9-(2-naphthylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexaazacyclotricosane-23-carboxamide 【CA登记号】 |
【 分 子 式 】C70H85N15O13S 【 分 子 量 】1376.6042 【元素组成】C 61.08% H 6.22% N 15.26% O 15.11% S 2.33% |
合成路线1
该中间体在本合成路线中的序号：(XVI)Elimination of the Boc protecting group of (XV) with trifluoroacetic acid followed by acetylation of the free amino group with acetic anhydride yielded resin (XVI) with a terminal acetyl group. Finally, this resin was treated with FH, anisole and dithioethane to complete the deprotection process and elimnate the solid phase resin affornig the target macrocyclic peptide.
| 【1】 Al-Obeidi, F.A.; Sharma, S.D.; de L. Castrucci, A.; Kesterson, R.A.; Lu, D.; Hadley, M.E.; Cone, R.D.; Hruby, V.J.; Cyclic lactam alpha-melanotropin analogues of Ac-Nle4-cyclo[Asp5, D-Phe7,Lys10] alpha-melanocyte-stimulating hormone-(4-10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem 1995, 38, 18, 3454. |
| 【2】 Hadley, M.E.; Hruby, V.J.; Sharma, S.D. (University of Arizona); Peptides having potent antagonist and agonist bioactivities at melanocortin receptors. US 5731408 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 25487 | tert-butyl (1S)-1-([[(3S,6S,9R,12S,15S,23S)-23-(aminocarbonyl)-12-([1-[(benzyloxy)methyl]-1H-imidazol-5-yl]methyl)-3-[(1-formyl-1H-indol-3-yl)methyl]-6-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-9-(2-naphthylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexaazacyclotricosan-15-yl]amino]carbonyl)pentylcarbamate | C73H91N15O14S | 详情 | 详情 | |
| (XVI) | 25488 | (3S,6S,9R,12S,15S,23S)-15-[[(2S)-2-(acetamido)hexanoyl]amino]-12-([1-[(benzyloxy)methyl]-1H-imidazol-5-yl]methyl)-3-[(1-formyl-1H-indol-3-yl)methyl]-6-[3-[(imino[[(4-methylphenyl)sulfonyl]amino]methyl)amino]propyl]-9-(2-naphthylmethyl)-2,5,8,11,14,17-hexaoxo-1,4,7,10,13,18-hexaazacyclotricosane-23-carboxamide | C70H85N15O13S | 详情 | 详情 |