N-benzyl-2-(benzyloxy)benzamide | 881227-12-9

• 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-benzyl-2-(benzyloxy)benzamide
• 英文别名: N-benzyl-2-phenylmethoxybenzamide
• CAS: 881227-12-9
• 化学式: C₂₁H₁₉NO₂
• mdl: MFCD07135697
• 分子量: 317.387
• InChiKey: GJNREGQQILABEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.095
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  yttrium(III) nitrate 、 N-benzyl-2-(benzyloxy)benzamide 以 乙酸乙酯 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  含新型酰胺型配体的铽、钕和钇配合物的合成、晶体结构和发光性能

  摘要：

  铽、钕和钇硝酸盐与酰胺型配体 N-苄基-2-（苄氧基）苯甲酰胺 (L) 的固体配合物已在乙酸乙酯中制备，并通过元素分析和红外光谱表征。配合物TbL3 (NO3) 3 、NdL3 (NO3) 3 和YL3 (NO3) 3 的晶体和分子结构已通过单晶X射线衍射确定。配合物的晶体结构相似。结构表明该晶体由不对称单元中的两个相似但独立的分子组成，金属离子与九个供体原子配位，其中三个属于三个单齿配体的氧原子和三个双齿硝酸盐的六个氧原子。此外，REL3 (NO) 3 复合单元通过分子间氢键连接形成三维网络。同时

  DOI：

  10.1002/zaac.200700416
• 作为产物：
  描述：

  溴甲苯 在 吡啶 、 氯化亚砜 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 N-benzyl-2-(benzyloxy)benzamide
  参考文献：
  名称：

  Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor

  摘要：

  The sphingomyelin synthase 2 (SMS2) is a potential target for pharmacological intervention in atherosclerosis. However, so far, few selective SMS2 inhibitors and their pharmacological activities were reported. In this study, a class of 2-benzyloxybenzamides were discovered as novel SMS2 inhibitors through scaffold hopping and structural optimization. Among them, Ly93 as one of the most potent inhibitors exhibited IC50 values of 91 nM and 133.9 mu M against purified SMS2 and SMS1 respectively. The selectivity ratio of Ly93 was more than 1400-fold for purified SMS2 over SMS1. The in vitro studies indicated that Ly93 not only dose-dependently diminished apoB secretion from Huh7 cells, but also significantly reduced the SMS activity and increased cholesterol efflux from macrophages. Meanwhile, Ly93 inhibited the secretion of LPS-mediated pro-inflammatory cytokine and chemokine in macrophages. The pharmacokinetic profiles of Ly93 performed on C57BL/6J mice demonstrated that Ly93 was orally efficacious. As a potent selective SMS2 inhibitor, Ly93 significantly decreased the plasma SM levels of C57BL/6J mice. Furthermore, Ly93 was capable of dose-dependently attenuating the atherosclerotic lesions in the root and the entire aorta as well as macrophage content in lesions, in apolipoprotein E gene knockout mice treated with Ly93. In conclusion, we discovered a novel selective SMS2 inhibitor Ly93 and demonstrated its anti-atherosclerotic activities in vivo. The preliminary molecular mechanism-of-action studies revealed its function in lipid homeostasis and inflammation process, which indicated that the selective inhibition of SMS2 would be a promising treatment for atherosclerosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.028