6-[4-(benzyloxy)phenoxy]nicotinic acid | 257609-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[4-(benzyloxy)phenoxy]nicotinic acid
• 英文别名: 6-(4-benzyloxyphenoxy)pyridine-3-carboxylic acid；6-[4-(Phenylmethoxy)phenoxy]-3-pyridinecarboxylic acid；6-(4-phenylmethoxyphenoxy)pyridine-3-carboxylic acid
• CAS: 257609-14-6
• 化学式: C₁₉H₁₅NO₄
• mdl: MFCD32880024
• 分子量: 321.332
• InChiKey: BHXHHTNDXMHVRL-UHFFFAOYSA-N

物化性质

• 沸点：
  520.6±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.052
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[4-(benzyloxy)phenoxy]nicotinic acid 、 4-(aminomethyl)pyridin-2-amine dihydrochloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到N-[(2-aminopyridin-4-yl)methyl]-6-(4-phenylmethoxyphenoxy)pyridine-3-carboxamide
  参考文献：
  名称：

  Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

  摘要：

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.052
• 作为产物：
  描述：

  6-[(4-benzyloxy)phenoxy]nicotinonitrile 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.75h， 以99%的产率得到6-[4-(benzyloxy)phenoxy]nicotinic acid
  参考文献：
  名称：

  Discovery of an N-(2-aminopyridin-4-ylmethyl)nicotinamide derivative: a potent and orally bioavailable NCX inhibitor

  摘要：

  Ca2+ overload in myocardial cells is responsible for arrhythmia. Sodium-calcium exchanger (NCX) inhibitors are more effective than sodium hydrogen exchanger (NHE) inhibitors with regard to modulation of Ca2+ overload, because NCX inhibitors can directly inhibit the influx of Ca2+ into cells. NCX is an attractive target for the treatment of heart failure and ischemia-reper-fusion. We have designed and synthesized a series of N-(2-aminopyridin-4-ylmethyl)nicotinamide derivatives, based on compound 5. We have discovered a novel NCX inhibitor (23h) with an IC50 value of 0.12 mu M against reverse NCX. The inhibitory activities of our NCX inhibitors against cytochrome P450 were also evaluated. The effects on heart failure and the pharmacokinetic profile of compound 23h are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.052

文献信息

• Anthranilic acid derivatives
  申请人：Teijin Limited

  公开号：US06649656B1

  公开（公告）日：2003-11-18

  The present invention relates to an anthranilic acid derivative expressed by the following formula (1) or the following formula (2), or its pharmacologically permissible salt or solvate.

  本发明涉及以下化学式（1）或以下化学式（2）所表示的邻氨基苯甲酸衍生物，或其在药理学上可接受的盐或溶剂化合物。
• Anthranilic acid derivative
  申请人：TEIJIN LIMITED

  公开号：US20030232811A1

  公开（公告）日：2003-12-18

  The present invention relates to an anthranilic acid derivative expressed by the following formula (1) or the following formula (2), or its pharmacologically permissible salt or solvate. 1

  本发明涉及下列式(1)或下列式(2)所表示的一个蒽酰氨基酸衍生物，或其药学上允许的盐或溶剂。1
• ANTHRANILIC ACID DERIVATIVES
  申请人：TEIJIN LIMITED

  公开号：EP1101755A1

  公开（公告）日：2001-05-23

  The present invention relates to an anthranilic acid derivative expressed by the following formula (1) or the following formula (2), or its pharmacologically permissible salt or solvate.

  本发明涉及一种由下式（1）或下式（2）表示的蒽酸衍生物，或其药理允许的盐或溶液。
• US6649656B1
  申请人：——

  公开号：US6649656B1

  公开（公告）日：2003-11-18
• US6890932B2
  申请人：——

  公开号：US6890932B2

  公开（公告）日：2005-05-10