(3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-acetamido-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-dibutyl-18-(4-hydroxybenzyl)-4-methyl-5,8,11,14,17,20-hexaoxo-4,7,10,13,16,19-hexaazatricosanedioic acid | 141611-95-2

• 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: (3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-acetamido-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-dibutyl-18-(4-hydroxybenzyl)-4-methyl-5,8,11,14,17,20-hexaoxo-4,7,10,13,16,19-hexaazatricosanedioic acid
• CAS: 141611-95-2
• 化学式: C₅₄H₇₀N₁₀O₁₄
• 分子量: 1083.21
• InChiKey: ZZCCFWWWVJVCDU-VLOLPVCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  78.0
• 可旋转键数：
  32.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  377.72
• 氢给体数：
  12.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-acetamido-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-dibutyl-18-(4-hydroxybenzyl)-4-methyl-5,8,11,14,17,20-hexaoxo-4,7,10,13,16,19-hexaazatricosanedioic acid 在 三氧化硫吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 生成 sodium 4-((2S,5S,8S,11S,17S,20S)-11-((1H-indol-3-yl)methyl)-20-((S)-2-acetamido-3-carboxypropanamido)-1-amino-2-benzyl-8,17-dibutyl-5-(carboxymethyl)-6-methyl-1,4,7,10,13,16,19-heptaoxo-3,6,9,12,15,18-hexaazahenicosan-21-yl)phenyl sulfate
  参考文献：
  名称：

  N-Methylated analogs of Ac[Nle28,31]CCK(26-33): synthesis, activity, and receptor selectivity

  摘要：

  A series of singularly N-methylated analogs of Ac[Nle28,31]CCK(26-33) were synthesized by the solid-phase methodology, and their biological activity was tested in three different in vitro bioassays. The bioassays employed were the guinea pig gallbladder (GPGB), stomach (GPS), and ileum (GPI). All N-methyl analogs were agonists in all three bioassays. N-Methylation at either N- or C-terminals did not affect potency and selectivity, whereas N-methylation of internal residues [Nle28,(N-Me)Nle31]- and [Nle28,31,(N-Me)Trp30]CCK(26-33) in the sequence resulted in analogs which were 10-fold less potent than Ac[Nle28,31]CCK(26-33) in all three preparations. Different rank orders of potencies observed for [Nle28,31,Sar29]- and [Nle28,31,(N-Me)Asp32]CCK(26-33) analogs correspond to increased selectivity to either GPGB or GPS, respectively. We propose that systematic N-methylation of single amide bonds in a bioactive peptide should be conducted as an additional routine to probe structure-activity relationships.

  DOI：

  10.1021/jm00093a013
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 N-Boc-L-正亮氨酸 、 N-叔丁氧羰基-N'-醛基-L-色氨酸 、 N^α-(tert-butyloxycarbonyl)-N^α-methyl-L-aspartic acid β-cyclohexyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (3S,6S,9S,15S,18S,21S)-9-((1H-indol-3-yl)methyl)-21-acetamido-3-(((S)-1-amino-1-oxo-3-phenylpropan-2-yl)carbamoyl)-6,15-dibutyl-18-(4-hydroxybenzyl)-4-methyl-5,8,11,14,17,20-hexaoxo-4,7,10,13,16,19-hexaazatricosanedioic acid
  参考文献：
  名称：

  N-Methylated analogs of Ac[Nle28,31]CCK(26-33): synthesis, activity, and receptor selectivity

  摘要：

  A series of singularly N-methylated analogs of Ac[Nle28,31]CCK(26-33) were synthesized by the solid-phase methodology, and their biological activity was tested in three different in vitro bioassays. The bioassays employed were the guinea pig gallbladder (GPGB), stomach (GPS), and ileum (GPI). All N-methyl analogs were agonists in all three bioassays. N-Methylation at either N- or C-terminals did not affect potency and selectivity, whereas N-methylation of internal residues [Nle28,(N-Me)Nle31]- and [Nle28,31,(N-Me)Trp30]CCK(26-33) in the sequence resulted in analogs which were 10-fold less potent than Ac[Nle28,31]CCK(26-33) in all three preparations. Different rank orders of potencies observed for [Nle28,31,Sar29]- and [Nle28,31,(N-Me)Asp32]CCK(26-33) analogs correspond to increased selectivity to either GPGB or GPS, respectively. We propose that systematic N-methylation of single amide bonds in a bioactive peptide should be conducted as an additional routine to probe structure-activity relationships.

  DOI：

  10.1021/jm00093a013