(E)-3-chloro-4-(3-fluoro-4-methoxyphenyl)salicylaldoxime | 1111084-79-7

• 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: (E)-3-chloro-4-(3-fluoro-4-methoxyphenyl)salicylaldoxime
• 英文别名: 2-chloro-3-(3-fluoro-4-methoxyphenyl)-6-[(E)-hydroxyiminomethyl]phenol
• CAS: 1111084-79-7
• 化学式: C₁₄H₁₁ClFNO₃
• 分子量: 295.698
• InChiKey: KLTZIZTUZXEBBT-REZTVBANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-chloro-4-(3-fluoro-4-methoxyphenyl)salicylaldehyde 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以62%的产率得到(E)-3-chloro-4-(3-fluoro-4-methoxyphenyl)salicylaldoxime
  参考文献：
  名称：

  Structural Evolutions of Salicylaldoximes as Selective Agonists for Estrogen Receptor β

  摘要：

  The bioisosteric replacement of the phenol ring, a signature functional group of most estrogen receptor (ER) ligands, with a hydrogen-bonded pseudocyclic ring, led to the development of a novel class of nonsteroidal ER-ligands based on a salicylaldoxime template. A series of structural modifications were applied to selected molecules belonging to the monoaryl-salicylaldoxime chemical class in an attempt to improve further their ER beta-selective receptor affinity and agonist properties. Among several modifications, the best results were obtained by the simultaneous introduction of a meta-fluorine atom into the para-hydroxyphenyl substituent present in the 4-position of salicylaldoxime, together with the insertion of a chloro group in the 3-position of the central scaffold. The resulting compound showed the best affinity (K-i = 7.1 nM) and selectivity for ER beta over ER alpha. Moreover, in transcription assays, it proved to be a selective and potent ER beta-full agonist with an EC50 of 4.8 nM.

  DOI：

  10.1021/jm801458t

文献信息

• [EN] ESTROGEN RECEPTOR BETA (ERβ) AGONISTS FOR THE TREATMENT OF FIBROTIC CONDITIONS<br/>[FR] AGONISTES DU RÉCEPTEUR BÊTA DES OESTROGÈNES (ERβ) POUR LE TRAITEMENT D'ÉTATS FIBROTIQUES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2020160225A1

  公开（公告）日：2020-08-06

  Disclosed are method of treating fibrotic conditions using estrogen receptor β (ERβ) agonists.
• [EN] METHODS OF MODULATING T-CELL ACTIVATION USING ESTROGEN RECEPTOR BETA (ERΒ) AGONISTS<br/>[FR] MÉTHODES DE MODULATION DE L'ACTIVATION DES LYMPHOCYTES T À L'AIDE D'AGONISTES DU RÉCEPTEUR BÊTA DES ŒSTROGÈNES (ERΒ)
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2021183760A1

  公开（公告）日：2021-09-16

  Disclosed are method of modulating immune response in a subject using ERβ agonists. The ERβ agonists can selectively inhibit the activation and/or proliferation of T-cells, reducing circulating T-cell levels in a subject without significantly affecting circulating levels of neutrophils, monocytes, or B-cells. As a result, the ERβ agonists can be used in therapeutic and/or prophylactic applications, including to treat or prevent chronic heart failure (CHF) in a subject post-myocardial infarction (MI) and to treat or prevent graft-versus-host disease (GVHD), multiple sclerosis (MS), and/or experimental autoimmune encephalomyelitis (EAE) in a subject.