di-tert-butyl ((2S,8R,15R,21S)-1,22-bis((S)-2-carbamoylpyrrolidin-1-yl)-2,21-bis(4-nitrobenzyl)-1,4,7,16,19,22-hexaoxo-11,12-dithia-3,6,17,20-tetraazadocosane-8,15-diyl)dicarbamate | 113132-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: di-tert-butyl ((2S,8R,15R,21S)-1,22-bis((S)-2-carbamoylpyrrolidin-1-yl)-2,21-bis(4-nitrobenzyl)-1,4,7,16,19,22-hexaoxo-11,12-dithia-3,6,17,20-tetraazadocosane-8,15-diyl)dicarbamate
• CAS: 113132-80-2
• 化学式: C₅₀H₇₀N₁₂O₁₆S₂
• 分子量: 1159.31
• InChiKey: XKJZQAUNBKXTKC-BAWVVKEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  80.0
• 可旋转键数：
  27.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  406.14
• 氢给体数：
  8.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl ((2S,8R,15R,21S)-1,22-bis((S)-2-carbamoylpyrrolidin-1-yl)-2,21-bis(4-nitrobenzyl)-1,4,7,16,19,22-hexaoxo-11,12-dithia-3,6,17,20-tetraazadocosane-8,15-diyl)dicarbamate 在 盐酸 、 苯甲醚 作用下， 以 溶剂黄146 为溶剂， 反应 0.75h， 以8.13 g的产率得到(2S,2'S)-1,1'-((2S,8R,15R,21S)-8,15-diamino-2,21-bis(4-nitrobenzyl)-4,7,16,19-tetraoxo-11,12-dithia-3,6,17,20-tetraazadocosanedioyl)bis(pyrrolidine-2-carboxamide) hydrochloride
  参考文献：
  名称：

  Peripherally acting enkephalin analogs. 1. Polar pentapeptides

  摘要：

  The design, synthesis, and biological activity of a series of highly polar enkephalin-related pentapeptides are reported. These analogues incorporate structural features that exclude them from the central nervous system and thereby restrict their action to peripherally located receptors. Hydrophilic analogues were obtained by introduction of polar D-amino acid residues at position 2 and, in certain cases, by conversion of the N-terminal amino group of the Tyr residue to a guanidino function. The peptides were synthesized by classical solution methods. All compounds demonstrated in vitro opioid activity in the GPI and all were shown to possess antinociceptive activity in chemically induced writhing models. The analgesic effects were shown to be predominantly peripherally mediated by antagonism of antinociception with the peripheral antagonist N-methylnalorphine. Comparative data obtained in writhing and hot-plate tests were also supportive of a peripheral mode of action. Compound 13a, L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide (BW 443C), was identified as having a favorable pharmacological profile, indicating a high level of peripheral selectivity, and worthy of further investigation.

  DOI：

  10.1021/jm00400a012
• 作为产物：
  描述：

  3-[(2S)-2-苯胺基丙酰]-N-{[(2-甲基-2-丙基)氧基]羰基}-4-硝基-L-脯氨酰胺 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 乙醇 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.29h， 生成 di-tert-butyl ((2S,8R,15R,21S)-1,22-bis((S)-2-carbamoylpyrrolidin-1-yl)-2,21-bis(4-nitrobenzyl)-1,4,7,16,19,22-hexaoxo-11,12-dithia-3,6,17,20-tetraazadocosane-8,15-diyl)dicarbamate
  参考文献：
  名称：

  Peripherally acting enkephalin analogs. 1. Polar pentapeptides

  摘要：

  The design, synthesis, and biological activity of a series of highly polar enkephalin-related pentapeptides are reported. These analogues incorporate structural features that exclude them from the central nervous system and thereby restrict their action to peripherally located receptors. Hydrophilic analogues were obtained by introduction of polar D-amino acid residues at position 2 and, in certain cases, by conversion of the N-terminal amino group of the Tyr residue to a guanidino function. The peptides were synthesized by classical solution methods. All compounds demonstrated in vitro opioid activity in the GPI and all were shown to possess antinociceptive activity in chemically induced writhing models. The analgesic effects were shown to be predominantly peripherally mediated by antagonism of antinociception with the peripheral antagonist N-methylnalorphine. Comparative data obtained in writhing and hot-plate tests were also supportive of a peripheral mode of action. Compound 13a, L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide (BW 443C), was identified as having a favorable pharmacological profile, indicating a high level of peripheral selectivity, and worthy of further investigation.

  DOI：

  10.1021/jm00400a012