N-[[N2-(tert-butoxycarbonyl)hydrazino]carbonyl]phenylalanylleucyl-NG-nitroarginyl-NG-nitroarginylisoleucine methyl ester | 102307-13-1

• 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: N-[[N2-(tert-butoxycarbonyl)hydrazino]carbonyl]phenylalanylleucyl-NG-nitroarginyl-NG-nitroarginylisoleucine methyl ester
• 英文别名: N-<2-(tert-butoxycarbonyl)hydrazino>carbonyl>phenylalanylleucyl-N^G-nitroarginyl-N^G-nitroarginylisoleucine methyl ester；N-{[N²-(tert-butoxycarbonyl)hydrazino]carbonyl}phenylalanylleucyl-N^G-nitroarginyl-N^G-nitroarginylisoleucine methyl ester
• CAS: 102307-13-1
• 化学式: C₄₀H₆₇N₁₅O₁₃
• 分子量: 966.065
• InChiKey: HNKLWYMTTXNSQK-POPCVQDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  68.0
• 可旋转键数：
  26.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  404.26
• 氢给体数：
  13.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-[[N2-(tert-butoxycarbonyl)hydrazino]carbonyl]phenylalanylleucyl-NG-nitroarginyl-NG-nitroarginylisoleucine methyl ester 在 palladium on activated charcoal 盐酸 、 anisole, glacial acetic acid 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 oxymorphone N-(hydrazinocarbonyl)phenylalanylleucylarginylarginylisoleucine methyl ester hydrochloride
  参考文献：
  名称：

  Peptides as receptor selectivity modulators of opiate pharmacophores

  摘要：

  In an effort to investigate whether "address" segments of endogenous opioid peptides, which are responsible for modulating receptor selectivity, also could modulate the selectivity of opioid alkaloid pharmacophores, we have synthesized analogues of leucine-enkephalin and dynorphin in which the N-terminal dipeptide "message" sequence has been replaced by oxymorphone or naltrexone. A hydrazone group was employed as a linkage between the alkaloids and peptides. The binding data for mu, kappa, and delta receptors indicate that peptide portions of the analogues can modulate the receptor selectivity of the attached alkaloid pharmacophores. The selectivity for different opioid receptor types depends on a balance between the affinities of the message and address components. In cases where these components have comparable receptor affinities, the address can significantly shift selectivity by increasing affinity to one receptor type while reducing affinity to other types. When the message component has high affinity for a particular receptor type, the modulatory role of the address is expressed mainly by reducing the affinity of the ligand for other opioid receptor types.

  DOI：

  10.1021/jm00157a018
• 作为产物：
  描述：

  N-<carbonyl>phenylalanylleucine benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 反应 21.5h， 生成 N-[[N2-(tert-butoxycarbonyl)hydrazino]carbonyl]phenylalanylleucyl-NG-nitroarginyl-NG-nitroarginylisoleucine methyl ester
  参考文献：
  名称：

  Peptides as receptor selectivity modulators of opiate pharmacophores

  摘要：

  In an effort to investigate whether "address" segments of endogenous opioid peptides, which are responsible for modulating receptor selectivity, also could modulate the selectivity of opioid alkaloid pharmacophores, we have synthesized analogues of leucine-enkephalin and dynorphin in which the N-terminal dipeptide "message" sequence has been replaced by oxymorphone or naltrexone. A hydrazone group was employed as a linkage between the alkaloids and peptides. The binding data for mu, kappa, and delta receptors indicate that peptide portions of the analogues can modulate the receptor selectivity of the attached alkaloid pharmacophores. The selectivity for different opioid receptor types depends on a balance between the affinities of the message and address components. In cases where these components have comparable receptor affinities, the address can significantly shift selectivity by increasing affinity to one receptor type while reducing affinity to other types. When the message component has high affinity for a particular receptor type, the modulatory role of the address is expressed mainly by reducing the affinity of the ligand for other opioid receptor types.

  DOI：

  10.1021/jm00157a018