KNT-63 | 1186029-20-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Oxamorphinans
• 英文名称: KNT-63
• 英文别名: KTN-63；(1S,2S,6R,14R,15S,16S)-5-(cyclopropylmethyl)-11,15-dihydroxy-N-phenyl-13,17-dioxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-triene-16-carboxamide
• CAS: 1186029-20-8
• 化学式: C₂₈H₃₀N₂O₅
• 分子量: 474.557
• InChiKey: YYNRSCGPLWDLNI-SXYWCRSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,2S,6R,14R,15S,16S)-5-(cyclopropylmethyl)-15-hydroxy-11-methoxy-N-phenyl-13,17-dioxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-triene-16-carboxamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到KNT-63
  参考文献：
  名称：

  Drug design and synthesis of a novel κ opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology

  摘要：

  A conformational analysis of kappa opioid receptor agonists, TRK-820 and U-50,488H indicated an active conformation of TRK-820 in which the C-ring was in the boat form with the 14-OH interacting with the amide nitrogen. Based on the obtained active conformation of TRK-820, we designed and synthesized a novel kappa agonist KNT-63 with oxabicyclo[2.2.2]octane skeleton. KNT-63 showed profound antinociceptive effects via the kappa receptor which were as potent as that of TRK-820. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.027

文献信息

• Drug design and synthesis of a novel κ opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology
  作者：Hiroshi Nagase、Akio Watanabe、Toru Nemoto、Noriyuki Yamaotsu、Kohei Hayashida、Mayumi Nakajima、Ko Hasebe、Kaoru Nakao、Hidenori Mochizuki、Shuichi Hirono、Hideaki Fujii

  DOI：10.1016/j.bmcl.2009.11.027

  日期：2010.1

  A conformational analysis of kappa opioid receptor agonists, TRK-820 and U-50,488H indicated an active conformation of TRK-820 in which the C-ring was in the boat form with the 14-OH interacting with the amide nitrogen. Based on the obtained active conformation of TRK-820, we designed and synthesized a novel kappa agonist KNT-63 with oxabicyclo[2.2.2]octane skeleton. KNT-63 showed profound antinociceptive effects via the kappa receptor which were as potent as that of TRK-820. (C) 2009 Elsevier Ltd. All rights reserved.