N-(1-苄基哌啶-4-基)异喹啉-5-胺 | 709045-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-(1-苄基哌啶-4-基)异喹啉-5-胺
• 英文名称: N-(1-benzylpiperidin-4-yl)isoquinolin-5-amine
• CAS: 709045-99-8
• 化学式: C₂₁H₂₃N₃
• 分子量: 317.434
• InChiKey: GQHKTVBEIBEQOC-UHFFFAOYSA-N

物化性质

• 沸点：
  498.4±45.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 在 titanium(IV) isopropylate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N-(1-苄基哌啶-4-基)异喹啉-5-胺
  参考文献：
  名称：

  Design and synthesis of rho kinase inhibitors (III)

  摘要：

  The structure-activity relationship of Rho kinase inhibitors bearing an isoquinoline scaffold was studied. N-(1-Benzyl-3-pyrrolidyl)-N-(5-isoquinolyl)amine analogues were optimized with respect to their inhibitory potencies for the enzyme and for chemotaxis. The potent analogues were further evaluated by an ex vivo test in which the selected compounds were orally administered to rats, and the Rho kinase inhibitory potency observed in the rat serum was evaluated 3 h after the administration. Compound 23g showed a high level of Rho kinase inhibitory activity in the rat serum and was stable in an in vitro metabolic test using a microsomal cytochrome preparation. The (R)-isomer of 23g displayed a higher level of inhibitory potency than the (S)-isomer in a cell-free kinase assay and in the cell migration assay (IC50ENZ = 25 nM and IC50MCP = 1 mu M). The (R)-isomer successfully inhibited the phosphorylation of MBS (myosin-binding subunit) in cells. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.028

文献信息

• Design and synthesis of Rho kinase inhibitors (I)
  作者：Atsuya Takami、Masayuki Iwakubo、Yuji Okada、Takehisa Kawata、Hideharu Odai、Nobuaki Takahashi、Kazutoshi Shindo、Kaname Kimura、Yoshimichi Tagami、Mika Miyake、Kayoko Fukushima、Masaki Inagaki、Mutsuki Amano、Kozo Kaibuchi、Hiroshi Iijima

  DOI：10.1016/j.bmc.2004.02.025

  日期：2004.5

  Several structurally unrelated scaffolds of the Rho kinase inhibitor were designed using pharmacophore information obtained from the results of a high-throughput screening and structural information from a homology model of Rho kinase. A docking simulation using the ligand-binding pocket of the Rho kinase model helped to comprehensively understand and to predict the structure-activity relationship of the inhibitors. This understanding was useful for developing new Rho kinase inhibitors of higher potency and selectivity. We identified several potent platforms for developing the Rho kinase inhibitors, namely, pyridine, 1H-indazole, isoquinoline, and phthalimide. (C) 2004 Elsevier Ltd. All rights reserved.