5-[3-(4-amino-2,5-diethoxy-benzyl)-ureido]-2-ethoxy-N-(4-methoxy-benzyl)-benzamide

• 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: 5-[3-(4-amino-2,5-diethoxy-benzyl)-ureido]-2-ethoxy-N-(4-methoxy-benzyl)-benzamide
• 英文别名: 5-[(4-amino-2,5-diethoxyphenyl)methylcarbamoylamino]-2-ethoxy-N-[(4-methoxyphenyl)methyl]benzamide
• 化学式: C₂₉H₃₆N₄O₆
• 分子量: 536.628
• InChiKey: CLEYDHXNXPLQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[3-(4-amino-2,5-diethoxy-benzyl)-ureido]-2-ethoxy-N-(4-methoxy-benzyl)-benzamide 、 甲基磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以52.6%的产率得到5-[3-(2,5-diethoxy-4-methylsulfonylamino-benzyl)-ureido]-2-ethoxy-N-(4-methoxy-benzyl)-benzamide
  参考文献：
  名称：

  一种基于4-甲氧基-苄基的取代苯甲酰胺新化合物、制备方法及用途

  摘要：

  本发明提供了一种新化合物，该化合物的名称为5-[3-（2,5-二乙氧基-4-甲磺酰基-苄基）-脲基]-2-乙氧基-N-（4-甲氧基苄基）-苯甲酰胺，该化合物的分子量为614.7，该化合物的结构见结构式（化合物1）；同时本发明提供了该化合物1的制备方法；本发明提供的化合物有较好的类药性，可用于新药研究领域尤其是II型糖尿病创新药物研究领域。

  公开号：

  CN105820094A
• 作为产物：
  描述：

  2-ethoxy-5-nitrobenzoic acid 在 sodium tetrahydroborate 、 氯化亚砜 、 nickel(II) chloride hexahydrate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 5-[3-(4-amino-2,5-diethoxy-benzyl)-ureido]-2-ethoxy-N-(4-methoxy-benzyl)-benzamide
  参考文献：
  名称：

  The discovery of novel, potent ERR-alpha inverse agonists for the treatment of triple negative breast cancer

  摘要：

  The estrogen-related receptor alpha (ERR alpha) is an orphan receptor and a novel target for solid tumor therapy, conceivably through effects on the regulation of tumor cell energy metabolism associated with energy stress within solid tumor micro environments. Here we describe the discovery of novel potent inverse agonists of ERR alpha. In vitro, compound 11 potently inhibits ERR alpha's transcriptional activity by preventing endogenous PGC-1 alpha and ERR alpha binding and suppresses the proliferation of different human cancer cell lines and the migration of breast cancer cells (MDA-MB-231). In vivo, compound 11 demonstrates a strong inhibitory effect on the growth of human breast cancer xenografts (MDA-MB-231) and the tumor growth is inhibited by 40.9% after treating with compound 11 (30 mg/kg). The binding mode shows that compound 11 interacts with the binding pocket of ERR alpha through hydrogen interactions with the residue Gly397 and hydrophobic interactions with the hydrophobic residues. All these results suggest that compound 11 represents a novel potent ERR alpha inverse agonist and is promising in the discovery of antitumor compounds for the treatment of triple negative breast cancer. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.04.050

文献信息

• The discovery of novel, potent ERR-alpha inverse agonists for the treatment of triple negative breast cancer
  作者：Yongli Du、Lianhua Song、Liudi Zhang、Hao Ling、Yanhui Zhang、Haifei Chen、Huijie Qi、Xiaojin Shi、Qunyi Li

  DOI：10.1016/j.ejmech.2017.04.050

  日期：2017.8

  The estrogen-related receptor alpha (ERR alpha) is an orphan receptor and a novel target for solid tumor therapy, conceivably through effects on the regulation of tumor cell energy metabolism associated with energy stress within solid tumor micro environments. Here we describe the discovery of novel potent inverse agonists of ERR alpha. In vitro, compound 11 potently inhibits ERR alpha's transcriptional activity by preventing endogenous PGC-1 alpha and ERR alpha binding and suppresses the proliferation of different human cancer cell lines and the migration of breast cancer cells (MDA-MB-231). In vivo, compound 11 demonstrates a strong inhibitory effect on the growth of human breast cancer xenografts (MDA-MB-231) and the tumor growth is inhibited by 40.9% after treating with compound 11 (30 mg/kg). The binding mode shows that compound 11 interacts with the binding pocket of ERR alpha through hydrogen interactions with the residue Gly397 and hydrophobic interactions with the hydrophobic residues. All these results suggest that compound 11 represents a novel potent ERR alpha inverse agonist and is promising in the discovery of antitumor compounds for the treatment of triple negative breast cancer. (C) 2017 Published by Elsevier Masson SAS.
• 一种基于4-甲氧基-苄基的取代苯甲酰胺新化合物、制备方法及用途
  申请人：齐鲁工业大学

  公开号：CN105820094A

  公开（公告）日：2016-08-03

  本发明提供了一种新化合物，该化合物的名称为5-[3-（2,5-二乙氧基-4-甲磺酰基-苄基）-脲基]-2-乙氧基-N-（4-甲氧基苄基）-苯甲酰胺，该化合物的分子量为614.7，该化合物的结构见结构式（化合物1）；同时本发明提供了该化合物1的制备方法；本发明提供的化合物有较好的类药性，可用于新药研究领域尤其是II型糖尿病创新药物研究领域。