methyl (6-fluoro-2-hydroxy-3-nitrophenyl)acetate | 361336-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl (6-fluoro-2-hydroxy-3-nitrophenyl)acetate
• 英文别名: Methyl 2-(6-fluoro-2-hydroxy-3-nitrophenyl)acetate
• CAS: 361336-91-6
• 化学式: C₉H₈FNO₅
• 分子量: 229.165
• InChiKey: OCNUAYJCINAGQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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 (6-fluoro-2-hydroxy-3-nitrophenyl)acetate 在 sodium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 (6-羟基-2-甲氧基-3-硝基-苯基)-乙酸
  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 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 methyl (6-fluoro-2-hydroxy-3-nitrophenyl)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

文献信息

• Polycyclic aryl and heteroaryl substituted benzenes useful for selective inhibition of the coagulation cascade
  申请人：——

  公开号：US20020025947A1

  公开（公告）日：2002-02-28

  The invention relates to polycyclic aryl and heteroaryl substituted benzene compounds useful as inhibitors of serine proteases of the coagulation cascade and compounds, compositions and methods for anticoagulant therapy for the treatment and prevention of a variety of thrombotic conditions including coronary artery and cerebrovascular diseases.

  本发明涉及可用作凝血级联丝氨酸蛋白酶抑制剂的多环芳基和杂芳基取代苯化合物，以及用于治疗和预防包括冠状动脉和脑血管疾病在内的各种血栓性疾病的抗凝疗法的化合物、组合物和方法。
• US6660885B2
  申请人：——

  公开号：US6660885B2

  公开（公告）日：2003-12-09
• US6852761B2
  申请人：——

  公开号：US6852761B2

  公开（公告）日：2005-02-08
• [EN] POLYCYCLIC ARYL AND HETEROARYL SUBSTITUTED BENZENES USEFUL FOR SELECTIVE INHIBITION OF THE COAGULATION CASCADE<br/>[FR] BENZENES POLYCYCLIQUES SUBSTITUES ARYLE ET HETEROARYLE UTILES POUR L'INHIBITION SELECTIVE DE LA CASCADE DE COAGULATION
  申请人：PHARMACIA CORP

  公开号：WO2001068605A1

  公开（公告）日：2001-09-20

  The invention relates to polycyclic aryl and heteroaryl substituted benzene compounds useful as inhibitors of serine proteases of the coagulation cascade and compounds, compositions and methods for anticoagulant therapy for the treatment and prevention of a variety of thrombotic conditions including coronary artery and cerebrovascular diseases.
• [EN] PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS<br/>[FR] COMPOSÉS PHARMACEUTIQUES POUR LE TRAITEMENT DE TROUBLES MÉDIÉS PAR LE COMPLÉMENT
  申请人：[en]ALEXION PHARMACEUTICALS, INC.

  公开号：WO2024035686A1

  公开（公告）日：2024-02-15

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