3-Nitro-4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid | 782430-95-9

• 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: 3-Nitro-4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid
• 英文别名: 3-nitro-4-(2-pyrrolidin-1-ylethoxy)benzoic acid
• CAS: 782430-95-9
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: KVVKPZZHFWRPHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Nitro-4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid 在 palladium on activated charcoal sodium tetrahydroborate 、 氯化亚砜 、 氢气 、 四氯化钛 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 42.0h， 生成 1-[2-[2-amino-4-[[2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl]methyl]phenoxy]ethyl]pyrrolidine
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 2. Exploring interactions at the proximal (S2) binding site

  摘要：

  In an effort to increase the thrombin inhibitory activity of a novel series of inhibitors (i.e., 1a), substituents were incorporated at the C-3" position of the C-3 aryl ring (2). Consistent with the X-ray crystallography studies, small hydrophobic groups at the C-3" site (Br and Me) enhanced thrombin inhibitory activity by 8-fold. However, a few more hydrophilic substituents (NO2 and OMe) also enhanced the potency of the series. The biological results are discussed in terms of molecular modeling studies. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00447-8
• 作为产物：
  描述：

  N-(2-羟乙基)-吡咯烷 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 76.0h， 生成 3-Nitro-4-[2-(1-pyrrolidinyl)ethoxy]benzoic acid
  参考文献：
  名称：

  Dibasic benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 2. Exploring interactions at the proximal (S2) binding site

  摘要：

  In an effort to increase the thrombin inhibitory activity of a novel series of inhibitors (i.e., 1a), substituents were incorporated at the C-3" position of the C-3 aryl ring (2). Consistent with the X-ray crystallography studies, small hydrophobic groups at the C-3" site (Br and Me) enhanced thrombin inhibitory activity by 8-fold. However, a few more hydrophilic substituents (NO2 and OMe) also enhanced the potency of the series. The biological results are discussed in terms of molecular modeling studies. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00447-8