methyl 4-amino-3-(3-pentyloxy)benzoate | 257292-09-4

• 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: methyl 4-amino-3-(3-pentyloxy)benzoate
• 英文别名: Methyl 4-amino-3-pentan-3-yloxybenzoate；methyl 4-amino-3-pentan-3-yloxybenzoate
• CAS: 257292-09-4
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: LIAZCMNIUGLBFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-amino-3-(3-pentyloxy)benzoate 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 Benzoic Acid Inhibitor 8
  参考文献：
  名称：

  Hydrophobic benzoic acids as inhibitors of influenza neuraminidase

  摘要：

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts In a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 mu M) over type B (B/Lee/40) influenza NA (IC50 500 mu M). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00197-2
• 作为产物：
  描述：

  4-氨基-3-羟基苯甲酸 在 硫酸 、 potassium carbonate 作用下， 反应 38.0h， 生成 methyl 4-amino-3-(3-pentyloxy)benzoate
  参考文献：
  名称：

  Hydrophobic benzoic acids as inhibitors of influenza neuraminidase

  摘要：

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts In a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 mu M) over type B (B/Lee/40) influenza NA (IC50 500 mu M). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00197-2

文献信息

• Hydrophobic benzoic acids as inhibitors of influenza neuraminidase
  作者：Venkatram R. Atigadda、Wayne J. Brouillette、Franco Duarte、Yarlagadda S. Babu、Shanta Bantia、Pooran Chand、Naiming Chu、John A. Montgomery、David A. Walsh、Elise Sudbeck、James Finley、Gillian M. Air、Ming Luo、Graeme W. Laver

  DOI：10.1016/s0968-0896(99)00197-2

  日期：1999.11

  Neuraminidase (NA) plays a critical role in the life cycle of influenza virus and is a target for new therapeutic agents. A new benzoic acid inhibitor (11) containing a lipophilic side chain at C-3 and a guanidine at C-5 was synthesized. The X-ray structure of 4-(N-acetylamino)-5-guanidino-3-(3-pentyloxy)benzoic acid in complex with NA revealed that the lipophilic side chain binds in a newly created hydrophobic pocket formed by the movement of Glu 278 to interact with Arg 226, whereas the guanidine of 11 interacts In a negatively charged pocket created by Asp 152, Glu 120 and Glu 229. Compound 11 was highly selective for type A (H2N2) influenza NA (IC50 1 mu M) over type B (B/Lee/40) influenza NA (IC50 500 mu M). (C) 1999 Elsevier Science Ltd. All rights reserved.