5-(3-氟-4-羟基苯基)-2-羟基苯甲醛 | 1098984-26-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(3-氟-4-羟基苯基)-2-羟基苯甲醛
• 英文名称: 5-(3-fluoro-4-hydroxyphenyl)salicylaldehyde
• 英文别名: 5-(3-fluoro-4-hydroxyphenyl)-salicylaldehyde；4-(3-Fluoro-4-hydroxyphenyl)-2-formylphenol；5-(3-fluoro-4-hydroxyphenyl)-2-hydroxybenzaldehyde
• CAS: 1098984-26-9
• 化学式: C₁₃H₉FO₃
• 分子量: 232.211
• InChiKey: UPXFYAVGWLVCAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-氟-4-羟基苯基)-2-羟基苯甲醛 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以81%的产率得到(E)-5-(3-fluoro-4-hydroxyphenyl)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
• 作为产物：
  描述：

  5-(3-氟-4-甲氧基苯基)-2-羟基苯甲醛 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到5-(3-氟-4-羟基苯基)-2-羟基苯甲醛
  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

• Inhibitors of protein kinase for the treatment of disease
  申请人：——

  公开号：US20030187007A1

  公开（公告）日：2003-10-02

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.

  本发明部分涉及使用基于酚和羟基萘的化合物调节蛋白激酶功能的方法。这些方法涉及表达蛋白激酶的细胞。此外，该发明描述了使用本发明鉴定的化合物预防和治疗生物体中与蛋白激酶相关的异常情况的方法。此外，该发明涉及基于酚和羟基萘的化合物以及包含这些化合物的药物组合物。
• INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE
  申请人：LG Biomedical Institute

  公开号：EP1412327A2

  公开（公告）日：2004-04-28
• [EN] INHIBITORS OF PROTEIN KINASE FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE LA PROTEINE KINASE DESTINES AU TRAITEMENT D'UNE MALADIE
  申请人：LG BIOMEDICAL INST

  公开号：WO2002096867A2

  公开（公告）日：2002-12-05

  The present invention is directed in part towards methods of modulating the function of protein kinases with phenol- and hydroxynaphthalene-based compounds. The methods incorporate cells that express a protein kinase. In addition, the invention describes methods of preventing and treating protein kinase-related abnormal conditions in organisms with a compound identified by the invention. Furthermore, the invention pertains to phenol- and hydroxynaphthalene-based compounds and pharmaceutical compositions comprising these compounds.
• Structural Evolutions of Salicylaldoximes as Selective Agonists for Estrogen Receptor β
  作者：Filippo Minutolo、Simone Bertini、Carlotta Granchi、Teresa Marchitiello、Giovanni Prota、Simona Rapposelli、Tiziano Tuccinardi、Adriano Martinelli、Jillian R. Gunther、Kathryn E. Carlson、John A. Katzenellenbogen、Marco Macchia

  DOI：10.1021/jm801458t

  日期：2009.2.12

  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.