4-methoxy-N-(2-(naphthalen-2-yl)ethyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methoxy-N-(2-(naphthalen-2-yl)ethyl)benzamide
• 英文别名: 4-methoxy-N-(2-naphthalen-2-ylethyl)benzamide
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: HAGWBKLGUKJPRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 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：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-萘-2-乙胺 、 大茴香酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到4-methoxy-N-(2-(naphthalen-2-yl)ethyl)benzamide
  参考文献：
  名称：

  Aryl amide small-molecule inhibitors of microRNA miR-21 function

  摘要：

  MicroRNAs (miRNAs) are single stranded RNA molecules of similar to 22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.016

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DES MALADIES RESPIRATOIRES
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2010022355A1

  公开（公告）日：2010-02-25

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).
• Aryl amide small-molecule inhibitors of microRNA miR-21 function
  作者：Yuta Naro、Meryl Thomas、Matthew D. Stephens、Colleen M. Connelly、Alexander Deiters

  DOI：10.1016/j.bmcl.2015.07.016

  日期：2015.11

  MicroRNAs (miRNAs) are single stranded RNA molecules of similar to 22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies. (C) 2015 Elsevier Ltd. All rights reserved.