3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthaldehyde
• 英文别名: 3-(3-Fluoro-4-hydroxy-phenyl)-7-hydroxy-naphthalene-1-carbaldehyde；3-(3-fluoro-4-hydroxyphenyl)-7-hydroxynaphthalene-1-carbaldehyde
• 化学式: C₁₇H₁₁FO₃
• 分子量: 282.271
• InChiKey: DYHJXPWBSPNTRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthaldehyde 、 丙二腈 在 pyridine hydrochloride salt 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到2-((3-(3-fluoro-4-hydroxyphenyl)-7-hydroxynaphthalen-1-yl)methylene)propanedinitrile
  参考文献：
  名称：

  用于活细胞中雌激素受体β成像的高亲和力亚型选择性荧光探针†

  摘要：

  雌激素受体β（ERβ）最近已被确定为乳腺癌荷尔蒙替代疗法的药物靶标。然而，ERβ在疾病进展中的生物学功能仍不清楚。发现具有高ERβ选择性的荧光探针（FPNM）对ERβ表现出纳摩尔摩尔亲和力，其ERβ/ERα选择性高达80，可以对细胞内ERβ进行特异性标记。此外，首次通过FPNM染色直接观察到各种细胞生物环境（例如前列腺癌（DU-145）或三阴性乳腺癌（MDA-MB-231））中不同的ERβ动态。

  DOI：

  10.1039/c8cc00483h
• 作为产物：
  描述：

  3-(3-氟-4-羟基苯基)-7-羟基萘-1-甲腈 在 咪唑 、 四丁基氟化铵 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.17h， 生成 3-(3-fluoro-4-hydroxyphenyl)-7-hydroxy-1-naphthaldehyde
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s

文献信息

• ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity
  作者：Richard E. Mewshaw、Richard J. Edsall,、Cuijian Yang、Eric S. Manas、Zhang B. Xu、Ruth A. Henderson、James C. Keith,、Heather A. Harris

  DOI：10.1021/jm058173s

  日期：2005.6.1

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.
• A high-affinity subtype-selective fluorescent probe for estrogen receptor β imaging in living cells
  作者：Zhiye Hu、Lu Yang、Wentao Ning、Chu Tang、Qiuyu Meng、Jie Zheng、Chune Dong、Hai-Bing Zhou

  DOI：10.1039/c8cc00483h

  日期：——

  Estrogen receptor β (ERβ) has recently been identified as a pharmaceutical target in hormone replacement therapy for breast cancers. However, the biological function of ERβ in disease progression remains unclear. A highly ERβ-selective fluorescent probe (FPNM) was discovered exhibiting nanomolar affinity for ERβ with an ERβ/ERα selectivity as high as 80, which allowed specific labeling of intracellular

  雌激素受体β（ERβ）最近已被确定为乳腺癌荷尔蒙替代疗法的药物靶标。然而，ERβ在疾病进展中的生物学功能仍不清楚。发现具有高ERβ选择性的荧光探针（FPNM）对ERβ表现出纳摩尔摩尔亲和力，其ERβ/ERα选择性高达80，可以对细胞内ERβ进行特异性标记。此外，首次通过FPNM染色直接观察到各种细胞生物环境（例如前列腺癌（DU-145）或三阴性乳腺癌（MDA-MB-231））中不同的ERβ动态。