ethyl 6-[5-(adamant-1-yl)-4-hydroxy-2-methylphenyl]-5-chloro-2-naphthoate | 1160658-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 6-[5-(adamant-1-yl)-4-hydroxy-2-methylphenyl]-5-chloro-2-naphthoate
• 英文别名: Ethyl 6-[5-(1-adamantyl)-4-hydroxy-2-methylphenyl]-5-chloronaphthalene-2-carboxylate
• CAS: 1160658-19-4
• 化学式: C₃₀H₃₁ClO₃
• 分子量: 475.027
• InChiKey: RALCQWGJNASNHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-[5-(adamant-1-yl)-4-hydroxy-2-methylphenyl]-5-chloro-2-naphthoate 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到6-[5-(adamant-1-yl)-4-hydroxy-2-methylbiphenyl]-4-chloro-2-naphthoic acid
  参考文献：
  名称：

  Highly twisted adamantyl arotinoids: Synthesis, antiproliferative effects and RXR transactivation profiles

  摘要：

  Retinoid-related molecules with an adamantyl group (adamantyl arotinoids) have been described with selective activities towards the retinoid receptors as agonists for NR1B2 and NR1B3 (RAR beta,gamma) (CD437, MX3350-1) or RAR antagonists (MX781) that induce growth arrest and apoptosis in cancer cells. Since these molecules induce apoptosis independently of RAR transactivation, we set up to synthesize novel analogs with impaired RAR binding. Here we describe adamantyl arotinoids with 2,2'-disubstituted biaryl rings prepared using the Suzuki coupling of the corresponding fragments. Those with cinnamic and naphthoic acid end groups showed significant antiproliferative activity in several cancer cell lines, and this effect correlated with the induction of apoptosis as measured by caspase activity. Strikingly, some of these compounds, whereas devoid of RAR binding capacity, were able to activate RXR. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.011
• 作为产物：
  描述：

  ethyl 6-[5-(adamant-1-yl)-4-(tert-butyldimethylsilyloxy)-2-methylphenyl]-5-chloro-2-naphthoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到ethyl 6-[5-(adamant-1-yl)-4-hydroxy-2-methylphenyl]-5-chloro-2-naphthoate
  参考文献：
  名称：

  Highly twisted adamantyl arotinoids: Synthesis, antiproliferative effects and RXR transactivation profiles

  摘要：

  Retinoid-related molecules with an adamantyl group (adamantyl arotinoids) have been described with selective activities towards the retinoid receptors as agonists for NR1B2 and NR1B3 (RAR beta,gamma) (CD437, MX3350-1) or RAR antagonists (MX781) that induce growth arrest and apoptosis in cancer cells. Since these molecules induce apoptosis independently of RAR transactivation, we set up to synthesize novel analogs with impaired RAR binding. Here we describe adamantyl arotinoids with 2,2'-disubstituted biaryl rings prepared using the Suzuki coupling of the corresponding fragments. Those with cinnamic and naphthoic acid end groups showed significant antiproliferative activity in several cancer cell lines, and this effect correlated with the induction of apoptosis as measured by caspase activity. Strikingly, some of these compounds, whereas devoid of RAR binding capacity, were able to activate RXR. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.011