2-(pyridin-4-ylmethoxy)benzoic acid | 926209-76-9

• 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: 2-(pyridin-4-ylmethoxy)benzoic acid
• CAS: 926209-76-9
• 化学式: C₁₃H₁₁NO₃
• mdl: MFCD08310590
• 分子量: 229.235
• InChiKey: MSXCCHTWBPXRSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pyridin-4-ylmethoxy)benzoic acid 、 对氯苯胺 在 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V) 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到N-(4-chlorophenyl)-2-(pyridin-4-ylmethoxy)benzamide
  参考文献：
  名称：

  Conformation–activity relationship on novel 4-pyridylmethylthio derivatives with antiangiogenic activity

  摘要：

  We found 4-pyridylmethylthio derivative 1 to be very effective in using antiangiogenesis activity to prevent proliferation of HUVECs (Human Umbilical Vein Endothelial Cells), which was induced by vascular endothelial growth factor (VEGF). Compound 1 was equally effective in inhibiting VEGF receptor2 tyrosine kinase (KDR, IC50 = 26 nM). We deduced that the inhibition was the result of binding the catalytic domain of VEGF receptor2 tyrosine kinase in a similar fashion to both phthalazine derivative PTK787 2 and anthranylamide derivative AAL993 3. In this report, we will describe the conformational analyses, from ab initio MO calculation and X-ray crystallographic analyses, of compound 1 and the analogs, which include non-active 9, all in comparison with 2 and 3. The conformation-activity relationships suggest that a nonbonded intramolecular interaction between the sulfur and the carbonyl oxygen of 1 was very important in inhibiting KDR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.068
• 作为产物：
  描述：

  2-(pyridin-4-ylmethoxy)benzoic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到2-(pyridin-4-ylmethoxy)benzoic acid
  参考文献：
  名称：

  Conformation–activity relationship on novel 4-pyridylmethylthio derivatives with antiangiogenic activity

  摘要：

  We found 4-pyridylmethylthio derivative 1 to be very effective in using antiangiogenesis activity to prevent proliferation of HUVECs (Human Umbilical Vein Endothelial Cells), which was induced by vascular endothelial growth factor (VEGF). Compound 1 was equally effective in inhibiting VEGF receptor2 tyrosine kinase (KDR, IC50 = 26 nM). We deduced that the inhibition was the result of binding the catalytic domain of VEGF receptor2 tyrosine kinase in a similar fashion to both phthalazine derivative PTK787 2 and anthranylamide derivative AAL993 3. In this report, we will describe the conformational analyses, from ab initio MO calculation and X-ray crystallographic analyses, of compound 1 and the analogs, which include non-active 9, all in comparison with 2 and 3. The conformation-activity relationships suggest that a nonbonded intramolecular interaction between the sulfur and the carbonyl oxygen of 1 was very important in inhibiting KDR. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.068

文献信息

• Protease inhibitors
  申请人：SmithKline Beecham Corporation

  公开号：US20020173469A1

  公开（公告）日：2002-11-21

  The present invention provides compounds which inhibit proteases, including cathepsin K, pharmaceutical compositions of such compounds, and methods for treating diseases of excessive bone loss or cartilage or matrix degradation, including osteoporosis; gingival disease including gingivitis and periodontitis; arthritis, more specifically, osteoarthritis and rheumatoid arthritis; Paget's disease; hypercalcemia of malignancy; and metabolic bone disease, comprising inhibiting said bone loss or excessive cartilage or matrix degradation by administering to a patient in need thereof a compound of the present invention.

  本发明提供了一种抑制蛋白酶的化合物，包括卡他普星K，以及这些化合物的药物组合物和治疗骨量过度流失或软骨或基质降解疾病的方法，包括骨质疏松症；牙龈疾病，包括牙龈炎和牙周炎；关节炎，更具体地说是骨关节炎和类风湿性关节炎；帕吉特病；恶性高钙血症；以及代谢性骨病，通过向需要治疗的患者投与本发明的化合物来抑制骨量过度流失或过度软骨或基质降解。
• PROTEASE INHIBITORS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0934291A1

  公开（公告）日：1999-08-11
• EP0934291A4
  申请人：——

  公开号：EP0934291A4

  公开（公告）日：1999-08-11
• US5998470A
  申请人：——

  公开号：US5998470A

  公开（公告）日：1999-12-07
• US6057362A
  申请人：——

  公开号：US6057362A

  公开（公告）日：2000-05-02