[(S)-2-(1H-Benzoimidazol-2-ylmethyl)-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-carbamic acid tert-butyl ester | 902776-36-7

• 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: [(S)-2-(1H-Benzoimidazol-2-ylmethyl)-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(4S)-2-(1H-benzimidazol-2-ylmethyl)-3-oxo-4,5-dihydro-1H-2-benzazepin-4-yl]carbamate
• CAS: 902776-36-7
• 化学式: C₂₃H₂₆N₄O₃
• 分子量: 406.484
• InChiKey: TXCDVNYKNMDMBH-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-2-(1H-Benzoimidazol-2-ylmethyl)-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-carbamic acid tert-butyl ester 、 三氟乙酸 以96%的产率得到(S)-4-Amino-2-(1H-benzoimidazol-2-ylmethyl)-1,2,4,5-tetrahydro-benzo[c]azepin-3-one; compound with trifluoro-acetic acid
  参考文献：
  名称：

  New 2‘,6‘-Dimethyl-l-tyrosine (Dmt) Opioid Peptidomimetics Based on the Aba-Gly Scaffold. Development of Unique μ-Opioid Receptor Ligands

  摘要：

  The Aba-Gly scaffold, incorporated into Dmt-Tic ligands ( H-Dmt-Tic-Gly-NH-CH2-Ph,H-Dmt-Tic-Gly-NH-Ph, H-Dmt-Tic-NH-CH2-Bid), exhibited mixed mu/delta or delta opioid receptor activities with A agonism. Substitution of Tic by Aba-Gly coupled to -NH-CH2-Ph ( 1), -NH-Ph ( 2), or -Bid ( Bid) 1H-benzimidazole-2-yl) ( 3) shifted affinity ( Ki( mu)) 0.46, 1.48, and 19.9 nM, respectively), selectivity, and bioactivity to mu-opioid receptors. These compounds represent templates for a new class of lead opioid agonists that are easily synthesized and suitable for therapeutic pain relief.

  DOI：

  10.1021/jm0603264
• 作为产物：
  描述：

  Boc-Aba-Gly 在 N-甲基吗啉 、 溶剂黄146 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.17h， 生成 [(S)-2-(1H-Benzoimidazol-2-ylmethyl)-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-4-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  New 2‘,6‘-Dimethyl-l-tyrosine (Dmt) Opioid Peptidomimetics Based on the Aba-Gly Scaffold. Development of Unique μ-Opioid Receptor Ligands

  摘要：

  The Aba-Gly scaffold, incorporated into Dmt-Tic ligands ( H-Dmt-Tic-Gly-NH-CH2-Ph,H-Dmt-Tic-Gly-NH-Ph, H-Dmt-Tic-NH-CH2-Bid), exhibited mixed mu/delta or delta opioid receptor activities with A agonism. Substitution of Tic by Aba-Gly coupled to -NH-CH2-Ph ( 1), -NH-Ph ( 2), or -Bid ( Bid) 1H-benzimidazole-2-yl) ( 3) shifted affinity ( Ki( mu)) 0.46, 1.48, and 19.9 nM, respectively), selectivity, and bioactivity to mu-opioid receptors. These compounds represent templates for a new class of lead opioid agonists that are easily synthesized and suitable for therapeutic pain relief.

  DOI：

  10.1021/jm0603264