methyl 4-(N-acetylamino)-3-[N-(2-ethylbutanoyl)amino]benzoate | 257292-06-1

• 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-(N-acetylamino)-3-[N-(2-ethylbutanoyl)amino]benzoate
• CAS: 257292-06-1
• 化学式: C₁₆H₂₂N₂O₄
• 分子量: 306.362
• InChiKey: ABHAPEHDMDUWMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.5
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(N-acetylamino)-3-[N-(2-ethylbutanoyl)amino]benzoate 在 sodium hydroxide 作用下， 反应 2.0h， 以100%的产率得到4-(n-acetylamino)-3-[n-(2-ethylbutanoylamino)]benzoic acid
  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：

  3,4-二氨基苯甲酸 在 硫酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 46.5h， 生成 methyl 4-(N-acetylamino)-3-[N-(2-ethylbutanoyl)amino]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