Boc-NH-CH[(CH2)4-NH-Ac]-Bid | 912671-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: Boc-NH-CH[(CH2)4-NH-Ac]-Bid
• 英文别名: tert-butyl N-[(1S)-5-acetamido-1-(1H-benzimidazol-2-yl)pentyl]carbamate
• CAS: 912671-27-3
• 化学式: C₁₉H₂₈N₄O₃
• 分子量: 360.456
• InChiKey: CIQRNGNJSWJEOX-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-NH-CH[(CH2)4-NH-Ac]-Bid 、 三氟乙酸 反应 0.5h， 以90%的产率得到2TFA*H2N-CH[(CH2)4-NH-Ac]-Bid
  参考文献：
  名称：

  Effect of Lysine at C-Terminus of the Dmt-Tic Opioid Pharmacophore

  摘要：

  Substitution of Gly with side-chain-protected or unprotected Lys in lead compounds containing the opioid pharmacophore Dmt-Tic [H-Dmt-Tic-Gly-NH-CH2-Ph, A agonist/% antagonist; H-Dmt-Tic-Gly-NH-Ph, A agonist/% agonist; and H-Dmt-Tic-NH-CH2-Bid, delta agonist ( Bid) 1H-benzimidazole-2-yl)] yielded a new series of compounds endowed with distinct pharmacological activities. Compounds (1-10) included high delta- (K-i(delta) 0.068-0.64 nM) and mu-opioid affinities (K-i(u)) 0.13-5.50 nM), with a bioactivity that ranged from mu-opioid agonism {10, H-Dmt-Tic-NH-CH[(CH2)4-NH2]-Bid (IC50 GPI = 39.7 nM)} to a selective mu-opioid antagonist [3, H-Dmt-Tic-Lys-NH-CH2-Ph (pA(2)(mu) = 7.96)] and a selective mu-opioid antagonist [5, H-Dmt-Tic-Lys(Ac)-NH-Ph (pA(2)(delta) = 12.0)]. The presence of a Lys linker provides new lead compounds in the formation of opioid peptidomimetics containing the Dmt-Tic pharmacophore with distinct agonist and/or antagonist properties.

  DOI：

  10.1021/jm060741w
• 作为产物：
  描述：

  N^e-乙酰基-N^a-Boc-L-赖氨酸 在 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 5.0h， 生成 Boc-NH-CH[(CH2)4-NH-Ac]-Bid
  参考文献：
  名称：

  Effect of Lysine at C-Terminus of the Dmt-Tic Opioid Pharmacophore

  摘要：

  Substitution of Gly with side-chain-protected or unprotected Lys in lead compounds containing the opioid pharmacophore Dmt-Tic [H-Dmt-Tic-Gly-NH-CH2-Ph, A agonist/% antagonist; H-Dmt-Tic-Gly-NH-Ph, A agonist/% agonist; and H-Dmt-Tic-NH-CH2-Bid, delta agonist ( Bid) 1H-benzimidazole-2-yl)] yielded a new series of compounds endowed with distinct pharmacological activities. Compounds (1-10) included high delta- (K-i(delta) 0.068-0.64 nM) and mu-opioid affinities (K-i(u)) 0.13-5.50 nM), with a bioactivity that ranged from mu-opioid agonism {10, H-Dmt-Tic-NH-CH[(CH2)4-NH2]-Bid (IC50 GPI = 39.7 nM)} to a selective mu-opioid antagonist [3, H-Dmt-Tic-Lys-NH-CH2-Ph (pA(2)(mu) = 7.96)] and a selective mu-opioid antagonist [5, H-Dmt-Tic-Lys(Ac)-NH-Ph (pA(2)(delta) = 12.0)]. The presence of a Lys linker provides new lead compounds in the formation of opioid peptidomimetics containing the Dmt-Tic pharmacophore with distinct agonist and/or antagonist properties.

  DOI：

  10.1021/jm060741w

文献信息

• WO2008/16913
  申请人：——

  公开号：——

  公开（公告）日：——
• Effect of Lysine at C-Terminus of the Dmt-Tic Opioid Pharmacophore
  作者：Gianfranco Balboni、Valentina Onnis、Cenzo Congiu、Margherita Zotti、Yusuke Sasaki、Akihiro Ambo、Sharon D. Bryant、Yunden Jinsmaa、Lawrence H. Lazarus、Claudio Trapella、Severo Salvadori

  DOI：10.1021/jm060741w

  日期：2006.9.1

  Substitution of Gly with side-chain-protected or unprotected Lys in lead compounds containing the opioid pharmacophore Dmt-Tic [H-Dmt-Tic-Gly-NH-CH2-Ph, A agonist/% antagonist; H-Dmt-Tic-Gly-NH-Ph, A agonist/% agonist; and H-Dmt-Tic-NH-CH2-Bid, delta agonist ( Bid) 1H-benzimidazole-2-yl)] yielded a new series of compounds endowed with distinct pharmacological activities. Compounds (1-10) included high delta- (K-i(delta) 0.068-0.64 nM) and mu-opioid affinities (K-i(u)) 0.13-5.50 nM), with a bioactivity that ranged from mu-opioid agonism 10, H-Dmt-Tic-NH-CH[(CH2)4-NH2]-Bid (IC50 GPI = 39.7 nM)} to a selective mu-opioid antagonist [3, H-Dmt-Tic-Lys-NH-CH2-Ph (pA(2)(mu) = 7.96)] and a selective mu-opioid antagonist [5, H-Dmt-Tic-Lys(Ac)-NH-Ph (pA(2)(delta) = 12.0)]. The presence of a Lys linker provides new lead compounds in the formation of opioid peptidomimetics containing the Dmt-Tic pharmacophore with distinct agonist and/or antagonist properties.