ethyl (4-butylbenzoyl)glycinate

• 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: ethyl (4-butylbenzoyl)glycinate
• 英文别名: Ethyl 2-[(4-butylbenzoyl)amino]acetate
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: AQJWPYBRTCBIHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (4-butylbenzoyl)glycinate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以99%的产率得到(4-butylbenzoyl)glycine
  参考文献：
  名称：

  O-Alkyl Hydroxamates Display Potent and Selective Antileishmanial Activity

  摘要：

  Leishmania (L.) infantum causes visceral, cutaneous, and mucosal leishmaniasis in humans and canine leishmaniasis in dogs. Herein, we describe that O-alkyl hydroxamate derivatives displayed potent and selective in vitro activity against the amastigote stage of L. infantum while no activity was observed against promastigotes. Compound 5 showed potent in vivo activity against L. infantum. Moreover, the combination of compound 5 supported on gold nanoparticles and meglumine antimoniate was also effective in vivo and improved the activity of these compounds compared to that of the individual treatment. Docking studies showed that compound 5 did not reach highly conserved pocket C and established interactions with the semiconserved residues V44, A45, R242, and E243 in pocket A of LiSIR2rp1. The surface space determined by these four amino acids is not conserved in human sirtuins. Compound 5 represents a new class of selective ligands with antileishmanial activity.

  DOI：

  10.1021/acs.jmedchem.9b02016
• 作为产物：
  描述：

  4-丁基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 ethyl (4-butylbenzoyl)glycinate
  参考文献：
  名称：

  O-Alkyl Hydroxamates Display Potent and Selective Antileishmanial Activity

  摘要：

  Leishmania (L.) infantum causes visceral, cutaneous, and mucosal leishmaniasis in humans and canine leishmaniasis in dogs. Herein, we describe that O-alkyl hydroxamate derivatives displayed potent and selective in vitro activity against the amastigote stage of L. infantum while no activity was observed against promastigotes. Compound 5 showed potent in vivo activity against L. infantum. Moreover, the combination of compound 5 supported on gold nanoparticles and meglumine antimoniate was also effective in vivo and improved the activity of these compounds compared to that of the individual treatment. Docking studies showed that compound 5 did not reach highly conserved pocket C and established interactions with the semiconserved residues V44, A45, R242, and E243 in pocket A of LiSIR2rp1. The surface space determined by these four amino acids is not conserved in human sirtuins. Compound 5 represents a new class of selective ligands with antileishmanial activity.

  DOI：

  10.1021/acs.jmedchem.9b02016

文献信息

• <i>O</i>-Alkyl Hydroxamates Display Potent and Selective Antileishmanial Activity
  作者：Victoriano Corpas-López、Mavys Tabraue-Chávez、Yudibeth Sixto-López、Sonia Panadero-Fajardo、Fernando Alves de Lima Franco、José F. Domínguez-Seglar、Francisco Morillas-Márquez、Francisco Franco-Montalbán、Mónica Díaz-Gavilán、José Correa-Basurto、Julián López-Viota、Margarita López-Viota、José Pérez del Palacio、Mercedes de la Cruz、Nuria de Pedro、Joaquina Martín-Sánchez、José A. Gómez-Vidal

  DOI：10.1021/acs.jmedchem.9b02016

  日期：2020.6.11

  Leishmania (L.) infantum causes visceral, cutaneous, and mucosal leishmaniasis in humans and canine leishmaniasis in dogs. Herein, we describe that O-alkyl hydroxamate derivatives displayed potent and selective in vitro activity against the amastigote stage of L. infantum while no activity was observed against promastigotes. Compound 5 showed potent in vivo activity against L. infantum. Moreover, the combination of compound 5 supported on gold nanoparticles and meglumine antimoniate was also effective in vivo and improved the activity of these compounds compared to that of the individual treatment. Docking studies showed that compound 5 did not reach highly conserved pocket C and established interactions with the semiconserved residues V44, A45, R242, and E243 in pocket A of LiSIR2rp1. The surface space determined by these four amino acids is not conserved in human sirtuins. Compound 5 represents a new class of selective ligands with antileishmanial activity.