2-{4-Diisopropylamino-3,5-difluoro-6-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyridin-2-yloxy}-5-iodo-benzoic acid methyl ester | 873925-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-{4-Diisopropylamino-3,5-difluoro-6-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyridin-2-yloxy}-5-iodo-benzoic acid methyl ester
• CAS: 873925-63-4
• 化学式: C₂₈H₂₇F₂IN₄O₅
• 分子量: 664.447
• InChiKey: ILAJPJYLLLGGPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.81
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-{4-Diisopropylamino-3,5-difluoro-6-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyridin-2-yloxy}-5-iodo-benzoic acid methyl ester 在 镍 lithium hydroxide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 4-[6-(3-Carbamimidoyl-phenoxy)-4-diisopropylamino-3,5-difluoro-pyridin-2-yloxy]-2'-methyl-biphenyl-3-carboxylic acid
  参考文献：
  名称：

  The discovery of fluoropyridine-based inhibitors of the factor VIIa/TF complex—Part 2

  摘要：

  The activated factor VII/tissue factor complex (FVIIa/TF) is known to play a key role in the formation of blood clots. Inhibition of this complex may lead to new antithrombotic drugs. A fluoropyridine-based series of FVIIa/TF inhibitors was discovered which utilized a diisopropylamino group for binding in the S2 and S3 binding pockets of the active site of the enzyme complex. In this series, an enhancement in binding affinity was observed by substitution at the 5-position of the hydroxybenzoic acid side-chain. An X-ray crystal structure indicates that amides at this position may increase inhibitor binding affinity through interactions with the S1'/S2' pocket. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.076
• 作为产物：
  描述：

  4-di-isopropylaminotetrafluoropyridine 在 potassium carbonate 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 2-{4-Diisopropylamino-3,5-difluoro-6-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenoxy]-pyridin-2-yloxy}-5-iodo-benzoic acid methyl ester
  参考文献：
  名称：

  The discovery of fluoropyridine-based inhibitors of the factor VIIa/TF complex—Part 2

  摘要：

  The activated factor VII/tissue factor complex (FVIIa/TF) is known to play a key role in the formation of blood clots. Inhibition of this complex may lead to new antithrombotic drugs. A fluoropyridine-based series of FVIIa/TF inhibitors was discovered which utilized a diisopropylamino group for binding in the S2 and S3 binding pockets of the active site of the enzyme complex. In this series, an enhancement in binding affinity was observed by substitution at the 5-position of the hydroxybenzoic acid side-chain. An X-ray crystal structure indicates that amides at this position may increase inhibitor binding affinity through interactions with the S1'/S2' pocket. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.076