N-(4-(4-chlorobenzyloxy)benzyl)-1-(pyridin-4-yl)methanamin

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(4-chlorobenzyloxy)benzyl)-1-(pyridin-4-yl)methanamin
• 英文别名: 1-{4-[(4-chlorobenzyl)oxy]phenyl}-N-(pyridin-4-ylmethyl)methanamine；1-[4-[(4-chlorophenyl)methoxy]phenyl]-N-(pyridin-4-ylmethyl)methanamine
• 化学式: C₂₀H₁₉ClN₂O
• 分子量: 338.837
• InChiKey: BWZOAUPGLKFBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(4-氯苄基)氧基]苯甲醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 27.0h， 生成 N-(4-(4-chlorobenzyloxy)benzyl)-1-(pyridin-4-yl)methanamin
  参考文献：
  名称：

  Vanillin-derived antiproliferative compounds influence Plk1 activity

  摘要：

  We synthesized a series of vanillin-derived compounds and analyzed them in HeLa cells for their effects on the proliferation of cancer cells. The molecules are derivatives of the lead compound SBE13, a potent inhibitor of the inactive conformation of human polo-like kinase 1 (Plk1). Some of the new designs were able to inhibit cancer cell proliferation to a similar extent as the lead structure. Two of the compounds ((({4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine) and (({4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine)) were much stronger in their capacity to reduce HeLa cell proliferation and turned out to potently induce apoptosis and reduce Plk1 kinase activity in vitro. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2014.09.015

文献信息

• Discovery of substituted benzyloxy-benzylamine inhibitors of acetyltransferase Eis and their anti-mycobacterial activity
  作者：Allan H. Pang、Keith D. Green、Nishad Thamban Chandrika、Atefeh Garzan、Ankita Punetha、Selina Y.L. Holbrook、Melisa J. Willby、James E. Posey、Oleg V. Tsodikov、Sylvie Garneau-Tsodikova

  DOI：10.1016/j.ejmech.2022.114698

  日期：2022.11

  yielded highly potent (IC50 ∼ 1 μM) Eis inhibitors, which did not inhibit other acetyltransferases. Crystal structures of Eis in complexes with three of the inhibitors showed that the inhibitors were bound in the aminoglycoside binding site of Eis, consistent with the competitive mode of inhibition, as established by kinetics measurements. When tested in Mtb cultures, two inhibitors (47 and 55) completely

  结核病对氨基糖苷类卡那霉素 (KAN) 耐药的一个临床重要机制是其乙酰化是由结核分枝杆菌( Mtb ) 乙酰转移酶 Eis 上调所催化的。在寻找 Eis 抑制剂的过程中，我们发现了一种具有取代的苄氧基-苄胺支架的抑制剂。对该结构家族中 38 种化合物的构效关系研究产生了高效 (IC 50 ∼ 1 μM) Eis 抑制剂，该抑制剂不抑制其他乙酰转移酶。Eis 与三种抑制剂复合物的晶体结构表明，抑制剂结合在 Eis 的氨基糖苷结合位点上，这与通过动力学测量建立的竞争性抑制模式一致。当在Mtb培养物中进行测试时，两种抑制剂（47和55）完全消除了高度 KAN 抗性菌株Mtb mc 2 6230 K204 对 KAN 的抗性，这可能是由于 Eis 抑制作为主要机制。即使在不存在 KAN 的情况下，其中 13 种化合物对Mtb和其他分枝杆菌也具有毒性，但对非分枝杆菌或哺乳动物细胞没有毒性。这种与 Eis
• Vanillin-derived antiproliferative compounds influence Plk1 activity
  作者：Roberto Carrasco-Gomez、Sarah Keppner-Witter、Martina Hieke、Lisa Lange、Gisbert Schneider、Manfred Schubert-Zsilavecz、Ewgenij Proschak、Birgit Spänkuch

  DOI：10.1016/j.bmcl.2014.09.015

  日期：2014.11

  We synthesized a series of vanillin-derived compounds and analyzed them in HeLa cells for their effects on the proliferation of cancer cells. The molecules are derivatives of the lead compound SBE13, a potent inhibitor of the inactive conformation of human polo-like kinase 1 (Plk1). Some of the new designs were able to inhibit cancer cell proliferation to a similar extent as the lead structure. Two of the compounds (((4-[(6-chloropyridin-3-yl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine) and ((4-[(4-chlorophenyl)methoxy]-3-methoxyphenyl}methyl)(pyridin-4-ylmethyl)amine)) were much stronger in their capacity to reduce HeLa cell proliferation and turned out to potently induce apoptosis and reduce Plk1 kinase activity in vitro. (C) 2014 Published by Elsevier Ltd.