3-hydroxy-N-(4-methoxyphenethyl)-2-naphthamide | 42875-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxy-N-(4-methoxyphenethyl)-2-naphthamide
• 英文别名: 3-hydroxy-N-[2-(4-methoxyphenyl)ethyl]naphthalene-2-carboxamide
• CAS: 42875-98-9
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: VJWXLRADQQTOHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(4-甲氧苯基)乙胺 、 2-羟基-3-萘甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到3-hydroxy-N-(4-methoxyphenethyl)-2-naphthamide
  参考文献：
  名称：

  Synthesis of potent chemical inhibitors of dynamin GTPase

  摘要：

  Dynamin is a key regulatory protein in clathrin mediated endocytosis. Compared to genetic or immunological tools, small chemical dynamin inhibitors such as dynasore have the potential to study the dynamic nature of endocytic events in cells. Dynasore inhibits dynamin GTPase activity and transferrin uptake at IC(50) similar to 15 mu M but use in some biological applications requires more potent inhibitor than dynasore. Here, we chemically modified the side chains of dynasore and found that two derivatives, DD-6 and DD-11 more potently inhibited transferrin uptake (IC(50): 4.00 mu M for DD-6, 2.63 mu M for DD-11) and dynamin GTPase activity (IC(50:) 5.1 mu M for DD-6, 3.6 mu M for DD-11) than dynasore. The effect was reversible and they were washed more rapidly out than dynasore. TIRF microscopy showed that they stabilize the clathrin coats on the membrane. Our results indicated that new dynasore derivatives are more potent inhibitor of dynamin, displaying promise as leads for the development of more effective analogues for broader biological applications. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.092

文献信息

• Synthesis of potent chemical inhibitors of dynamin GTPase
  作者：Suho Lee、Kwan-Young Jung、Joohyun Park、Joong-Heui Cho、Yong-Chul Kim、Sunghoe Chang

  DOI：10.1016/j.bmcl.2010.06.092

  日期：2010.8

  Dynamin is a key regulatory protein in clathrin mediated endocytosis. Compared to genetic or immunological tools, small chemical dynamin inhibitors such as dynasore have the potential to study the dynamic nature of endocytic events in cells. Dynasore inhibits dynamin GTPase activity and transferrin uptake at IC(50) similar to 15 mu M but use in some biological applications requires more potent inhibitor than dynasore. Here, we chemically modified the side chains of dynasore and found that two derivatives, DD-6 and DD-11 more potently inhibited transferrin uptake (IC(50): 4.00 mu M for DD-6, 2.63 mu M for DD-11) and dynamin GTPase activity (IC(50:) 5.1 mu M for DD-6, 3.6 mu M for DD-11) than dynasore. The effect was reversible and they were washed more rapidly out than dynasore. TIRF microscopy showed that they stabilize the clathrin coats on the membrane. Our results indicated that new dynasore derivatives are more potent inhibitor of dynamin, displaying promise as leads for the development of more effective analogues for broader biological applications. (c) 2010 Elsevier Ltd. All rights reserved.