methyl (2-fluoro-6-hydroxy-3-nitrophenyl)acetate | 361340-51-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl (2-fluoro-6-hydroxy-3-nitrophenyl)acetate
• 英文别名: Methyl 2-(2-fluoro-6-hydroxy-3-nitrophenyl)acetate
• CAS: 361340-51-4
• 化学式: C₉H₈FNO₅
• 分子量: 229.165
• InChiKey: GRCNUYSNLMYHFA-UHFFFAOYSA-N

物化性质

• 沸点：
  389.5±42.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2-fluoro-6-hydroxy-3-nitrophenyl)acetate 在 四(三苯基膦)钯 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 methyl (4-amino-3'-{[(benzyloxy)carbonyl]amino}-3-fluoro-1,1'-biphenyl-2-yl)acetate
  参考文献：
  名称：

  Synthesis and Crystal Structures of Substituted Benzenes and Benzoquinones as Tissue Factor VIIa Inhibitors

  摘要：

  Several multistep syntheses of substituted benzenes are reported. The benzene analogues were designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor VIIa enzyme. A variety of chemical transformations including nucleophilic additions, reductive aminations, Stille couplings, and polymer-assisted solution-phase (PASP) techniques were used to prepare key intermediates and final products. The initial analogues identified some weakly active compounds which ultimately led to a 340 nM (IC50) tissue Factor VIIa inhibitor with selectivity over other related enzymes. The structure-activity relationship of these inhibitors and the synthetic progression from the discovery of the lead compound to the development of potent analogues will be discussed. The X-ray crystal structures of fluorobenzene 50c and benzoquinone 54 inhibitors complexed with the TF/VIIa enzyme will also be described.

  DOI：

  10.1021/jm030233b
• 作为产物：
  描述：

  2,6-二氟苯乙酸 在 吡啶 、 草酰氯 、 硝酸 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 三甲基乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 methyl (2-fluoro-6-hydroxy-3-nitrophenyl)acetate
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS
  [FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT

  摘要：

  This disclosure provides compounds, compositions, and methods to treat medical disorders, such as complement-mediated disorders, including complement C1s-mediated disorders.

  公开号：

  WO2024035686A1

文献信息

• Synthesis and X-ray crystal structures of substituted fluorobenzene and benzoquinone inhibitors of the tissue factor VIIa complex
  作者：John J. Parlow、Ravi G. Kurumbail、Roderick A. Stegeman、Anna M. Stevens、William C. Stallings、Michael S. South

  DOI：10.1016/j.bmcl.2003.08.002

  日期：2003.11

  Multistep syntheses of substituted benzenes and benzoquinone inhibitors of tissue Factor Vila are reported. The benzene analogues were designed such that their substitution pattern would occupy and interact with the S-1, S-2, and S-3 pockets of the tissue Factor Vila (TF/VIIa) enzyme. The compounds exhibited modest potency on TF/VIIa with selectivity over Factor Xa and thrombin. The X-ray crystal structures of the targeted fluorobenzene l2a and benzoquinone 14 inhibitors bound to TF/VIIa were obtained and will be described. (C) 2003 Elsevier Ltd. All rights reserved.