(2R,5'S,5''R,5'''R)-5'-(4-Azido-butyl)-4,5'''-dibenzyl-2-isopropyl-5'''-(3-methyl-but-2-enyl)-5''-naphthalen-1-ylmethyl-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone | 847020-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2R,5'S,5''R,5'''R)-5'-(4-Azido-butyl)-4,5'''-dibenzyl-2-isopropyl-5'''-(3-methyl-but-2-enyl)-5''-naphthalen-1-ylmethyl-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone
• CAS: 847020-46-6
• 化学式: C₅₃H₅₅N₇O₄
• 分子量: 854.064
• InChiKey: JJHGWIVULGVZOH-DGWDDASSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  64.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  165.16
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,5'S,5''R,5'''R)-5'-(4-Azido-butyl)-4,5'''-dibenzyl-2-isopropyl-5'''-(3-methyl-but-2-enyl)-5''-naphthalen-1-ylmethyl-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以61%的产率得到(2R,5'S,5''R,5'''R)-5'-(4-Amino-butyl)-4,5'''-dibenzyl-2-isopropyl-5'''-(3-methyl-but-2-enyl)-5''-naphthalen-1-ylmethyl-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  [(2R,5'S)-5'-(4-Azido-butyl)-4-benzyl-2-isopropyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-5'-yl]-acetaldehyde 在 盐酸 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 12.0h， 生成 (2R,5'S,5''R,5'''R)-5'-(4-Azido-butyl)-4,5'''-dibenzyl-2-isopropyl-5'''-(3-methyl-but-2-enyl)-5''-naphthalen-1-ylmethyl-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974