methyl 5-amino-2-(piperidin-1-yl)benzoate | 1116689-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl 5-amino-2-(piperidin-1-yl)benzoate
• 英文别名: methyl 5-amino-2-piperidin-1-ylbenzoate
• CAS: 1116689-33-8
• 化学式: C₁₃H₁₈N₂O₂
• mdl: MFCD13344467
• 分子量: 234.298
• InChiKey: GDVWBKZDTDVVAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-amino-2-(piperidin-1-yl)benzoate 、 3-(fur-2-yl)crotonic acid 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以78%的产率得到(E)-methyl 5-(3-(furan-2-yl)acrylamido)-2-(piperidin-1-yl)benzoate
  参考文献：
  名称：

  Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors

  摘要：

  Synthetic methods have been developed for lead Sortase A inhibitors identified from previous studies. Several derivatives of the lead inhibitor were synthesized to derive preliminary structure activity relationships (SAR). Different regions of the lead inhibitor that are critical for the enzyme activity have been determined by systematic SAR studies. The E stereochemistry of the lead compound was found to be critical for its activity. Replacement of the E double bond with Z double bond or a rigid triple bond reduced the enzyme inhibitory activity in most cases. Reduction of the double bond to a C-C single bond resulted in complete loss of activity. Amide carbonyl and NH groups were also found to be crucial for the activity of this class of inhibitors, as well. The morpholine ring oxygen atom was also found to be an important factor for the activity of the lead inhibitor. Preliminary SAR studies led to the identification of compounds with improved enzyme inhibition. The most active compound was found to have an IC(50) value of 58 mu M against the enzyme. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.024
• 作为产物：
  描述：

  3-nitro-6-(1-piperidinyl)benzoic acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以93%的产率得到methyl 5-amino-2-(piperidin-1-yl)benzoate
  参考文献：
  名称：

  Synthesis and structure activity relationship studies of novel Staphylococcus aureus Sortase A inhibitors

  摘要：

  Synthetic methods have been developed for lead Sortase A inhibitors identified from previous studies. Several derivatives of the lead inhibitor were synthesized to derive preliminary structure activity relationships (SAR). Different regions of the lead inhibitor that are critical for the enzyme activity have been determined by systematic SAR studies. The E stereochemistry of the lead compound was found to be critical for its activity. Replacement of the E double bond with Z double bond or a rigid triple bond reduced the enzyme inhibitory activity in most cases. Reduction of the double bond to a C-C single bond resulted in complete loss of activity. Amide carbonyl and NH groups were also found to be crucial for the activity of this class of inhibitors, as well. The morpholine ring oxygen atom was also found to be an important factor for the activity of the lead inhibitor. Preliminary SAR studies led to the identification of compounds with improved enzyme inhibition. The most active compound was found to have an IC(50) value of 58 mu M against the enzyme. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.024

文献信息

• Bi-aryl meta-pyrimidine inhibitors of kinases
  申请人：Noronha Glenn

  公开号：US20070259904A1

  公开（公告）日：2007-11-08

  The invention provides biaryl meta-pyrimidine compounds having the general structure (A). The pyrimidine compounds of the invention are capable of inhibiting kinases, such as members of the Jak kinase family, and various other specific receptor and non-receptor kinases.

  本发明提供了具有一般结构（A）的联苯基间吡嘧啶化合物。本发明的吡嘧啶化合物能够抑制激酶，如Jak激酶家族成员以及其他特定的受体和非受体激酶。
• Bi-Aryl Meta-Pyrimidine Inhibitors of Kinases
  申请人：Noronha Glenn

  公开号：US20090275582A1

  公开（公告）日：2009-11-05

  The invention provides biaryl meta-pyrimidine compounds having the general structure (A). The pyrimidine compounds of the invention are capable of inhibiting kinases, such as members of the Jak kinase family, and various other specific receptor and non-receptor kinases.

  本发明提供具有一般结构（A）的双芳基间位嘧啶化合物。本发明的嘧啶化合物能够抑制激酶，如Jak激酶家族的成员，以及各种其他特定的受体和非受体激酶。
• BI-ARYL META-PYRIMIDINE INHIBITORS OF KINASES
  申请人：Noronha Glenn

  公开号：US20110212077A1

  公开（公告）日：2011-09-01

  The invention provides biaryl meta-pyrimidine compounds having the general structure (A). The pyrimidine compounds of the invention are capable of inhibiting kinases, such as members of the Jak kinase family, and various other specific receptor and non-receptor kinases.

  本发明提供了具有一般结构（A）的双芳基间位嘧啶化合物。本发明的嘧啶化合物能够抑制激酶，例如Jak激酶家族的成员以及其他特定的受体和非受体激酶。
• US7528143B2
  申请人：——

  公开号：US7528143B2

  公开（公告）日：2009-05-05
• US7825246B2
  申请人：——

  公开号：US7825246B2

  公开（公告）日：2010-11-02