4-(2,2-bis (hydroxymethyl)-5-oxopyrrolidin-1-yl)-3-(2-ethylbut-1-enyl)benzoic acid | 1391713-23-7

• 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: 4-(2,2-bis (hydroxymethyl)-5-oxopyrrolidin-1-yl)-3-(2-ethylbut-1-enyl)benzoic acid
• 英文别名: 4-[2,2-Bis(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-(2-ethylbut-1-enyl)benzoic acid
• CAS: 1391713-23-7
• 化学式: C₁₉H₂₅NO₅
• 分子量: 347.411
• InChiKey: BOIJNHMNUWDKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,2-bis (hydroxymethyl)-5-oxopyrrolidin-1-yl)-3-(2-ethylbut-1-enyl)benzoic acid 在 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 以99%的产率得到4-(2,2-bis(hydroxymethyl)-5-oxopyrrolidin-1-yl)-3-(2-ethylbutyl)benzoic acid
  参考文献：
  名称：

  Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: The hydrophobic side chain influences type A subtype selectivity

  摘要：

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A series of influenza neuraminidase inhibitors with the pyrrolidinobenzoic acid scaffold containing lipophilic side chains at the C3 position have been synthesized and evaluated for influenza neuraminidase inhibitory activity. The size and geometry of the C3 side chains have been modified in order to investigate structure-activity relationships. The results indicated that size and geometry of the C3-side chain are important for selectivity of inhibition against N1 versus N2 NA, important type A influenza variants that infect man, including the highly lethal avian influenza. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.001
• 作为产物：
  描述：

  1-溴-2-乙基丁-1-烯 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 barium hydroxide octahydrate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 、 三氯化磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 4-(2,2-bis (hydroxymethyl)-5-oxopyrrolidin-1-yl)-3-(2-ethylbut-1-enyl)benzoic acid
  参考文献：
  名称：

  Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: The hydrophobic side chain influences type A subtype selectivity

  摘要：

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A series of influenza neuraminidase inhibitors with the pyrrolidinobenzoic acid scaffold containing lipophilic side chains at the C3 position have been synthesized and evaluated for influenza neuraminidase inhibitory activity. The size and geometry of the C3 side chains have been modified in order to investigate structure-activity relationships. The results indicated that size and geometry of the C3-side chain are important for selectivity of inhibition against N1 versus N2 NA, important type A influenza variants that infect man, including the highly lethal avian influenza. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.001

文献信息

• Pyrrolidinobenzoic acid inhibitors of influenza virus neuraminidase: The hydrophobic side chain influences type A subtype selectivity
  作者：Yanwu Li、Arundutt Silamkoti、Gundurao Kolavi、Liyuan Mou、Shelly Gulati、Gillian M. Air、Wayne J. Brouillette

  DOI：10.1016/j.bmc.2012.05.001

  日期：2012.7

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A series of influenza neuraminidase inhibitors with the pyrrolidinobenzoic acid scaffold containing lipophilic side chains at the C3 position have been synthesized and evaluated for influenza neuraminidase inhibitory activity. The size and geometry of the C3 side chains have been modified in order to investigate structure-activity relationships. The results indicated that size and geometry of the C3-side chain are important for selectivity of inhibition against N1 versus N2 NA, important type A influenza variants that infect man, including the highly lethal avian influenza. (C) 2012 Elsevier Ltd. All rights reserved.