N-苄基-邻氨基苯甲酸甲酯 | 39129-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-邻氨基苯甲酸甲酯
• 英文名称: methyl N-benzylideneanthranilate
• 英文别名: Methyl 2-[(phenylmethylene)amino]benzoate；methyl 2-(benzylideneamino)benzoate
• CAS: 39129-16-3
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: ZCFRWOFFFLZLDU-UHFFFAOYSA-N

物化性质

• 沸点：
  406.3±28.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• LogP：
  3.316 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苄基-邻氨基苯甲酸甲酯 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl 2-(benzylamino)benzoate
  参考文献：
  名称：

  Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series

  摘要：

  A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 +/- 0.1 mu M). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 +/- 0.6 and 3.1 +/- 1.05 mu M, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6 +/- 0.1 and 3.3 +/- 0.1 mu M, respectively) as well as 6 and 9 (both having IC50 values of <5 mu M). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.047
• 作为产物：
  描述：

  苯甲醛 、 邻氨基苯甲酸甲酯 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-苄基-邻氨基苯甲酸甲酯
  参考文献：
  名称：

  Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series

  摘要：

  A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3 +/- 0.1 mu M). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1 +/- 0.6 and 3.1 +/- 1.05 mu M, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6 +/- 0.1 and 3.3 +/- 0.1 mu M, respectively) as well as 6 and 9 (both having IC50 values of <5 mu M). Chemical modifications on the quinolinone-chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.047

文献信息

• Novel acetic acid derivatives containing quinazolin‐4(3 <i>H</i> )‐one ring: Synthesis, in vitro, and in silico evaluation of potent aldose reductase inhibitors
  作者：Feyzi Sinan Tokalı、Yeliz Demir、Cüneyt Türkeş、Büşra Dinçer、Şükrü Beydemir

  DOI：10.1002/ddr.22031

  日期：——

  Aldose reductase (AR) is a crucial enzyme of the polyol pathway through which glucose is metabolized under conditions of hyperglycemia related to diabetes. A series of novel acetic acid derivatives containing quinazolin-4(3H)-one ring (1–22) was synthesized and tested for in vitro AR inhibitory effect. All the target compounds exhibited nanomolar activity against the target enzyme, and all compounds

  醛糖还原酶（AR）是多元醇途径中的关键酶，在与糖尿病相关的高血糖条件下，葡萄糖通过该途径代谢。合成了一系列含有喹唑啉-4(3 H )-单环( 1-22 )的新型乙酸衍生物，并测试了其体外AR抑制作用。所有目标化合物均表现出针对目标酶的纳摩尔活性，并且与参比药物依帕司他相比，所有化合物均表现出更高的活性。其中，化合物19，命名为2-(4-[(2-[(4-甲基哌嗪-1-基)甲基]-4-氧代喹唑啉-3(4H ) -亚氨基)甲基]苯氧基)乙酸，显示出抑制作用最强，K I值为 61.20 ± 10.18 nM。此外，还使用 ​​MTT 测定研究了这些化合物针对 L929（非肿瘤成纤维细胞）和 MCF-7（乳腺癌细胞）的活性。化合物16和19对正常L929细胞显示出较低的毒性。还评估了合成化合物（1-22）的吸收、分布、代谢和排泄特性。分子对接模拟被用来研究这些抑制剂对抗 AR 的可能结合机制。
• Ytterbium triflate-catalyzed reactions of imines with a chiral non-racemic silyloxypyrrole
  作者：Bruno Dudot、Jacques Royer、Mireille Sevrin、Pascal George

  DOI：10.1016/s0040-4039(00)00625-0

  日期：2000.6

  In the presence of a catalytic amount of ytterbium triflate the reactions of various aromatic imines with a chiral non-racemic silyloxypyrrole proceeded smoothly to afford the corresponding aldol-type adducts in go od yields and diastereoselectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.