(+/-)-4-chloro-1-(4-fluorophenyl)butyl 4-phenylbutanoate | 1266676-21-4

• 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: (+/-)-4-chloro-1-(4-fluorophenyl)butyl 4-phenylbutanoate
• 英文别名: [4-Chloro-1-(4-fluorophenyl)butyl] 4-phenylbutanoate
• CAS: 1266676-21-4
• 化学式: C₂₀H₂₂ClFO₂
• 分子量: 348.845
• InChiKey: OBFSKLZLOQMSEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-氯苯基)-4-羟基哌啶 、 (+/-)-4-chloro-1-(4-fluorophenyl)butyl 4-phenylbutanoate 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以43%的产率得到4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butyl 4-phenylbutanoate
  参考文献：
  名称：

  Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells

  摘要：

  Complex mechanisms of prostate cancer progression prompt to novel therapeutic strategies concerning a combination of drugs or of single molecules able to interact with more crucial targets. Histone deacetylase inhibitors and sigma ligands with mixed sigma(1) antagonist and sigma(2) agonist properties were proposed as new potential tools for treatment of prostate cancer. (+/-)-MRJF4 was synthesized as phenylbutyrate ester of haloperidol metabolite II, which is a molecule consisting of a histone deacetilase inhibitor (4-phenylbutyric acid) and a sigma ligand (haloperidol metabolite II). Antiproliferatives activities of 4-phenylbutyric acid, haloperidol metabolite II, equimolar mixture of both compounds and (+/-)-MRJF4 were evaluated in vitro on LNCaP and PO prostate cancer cells. Preliminary binding studies of (+/-)-MRJF4 for sigma(1), sigma(2), D-2 and D-3 receptors and inhibition HDAC activity were reported. KIT cell viability assays highlighted a notable increase of antiproliferative activity of (+/-)-MRJF4 (IC50 = 11 and 13 mu M for LNCaP and PC3, respectively) compared to 4-phenylbutyric acid, haloperidol metabolite II and the respective equimolar pharmacological association. (+/-)-MRJF4 was also used in combination with sigma(1) agonist (+)-pentazocine and sigma(2) antagonist AC927 in order to evaluate the role of sigma receptor subtypes in prostate cancer cell death. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.012
• 作为产物：
  描述：

  alpha-(3-氯丙基)-4-氟苄醇 、 4-苯基丁酰氯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以60%的产率得到(+/-)-4-chloro-1-(4-fluorophenyl)butyl 4-phenylbutanoate
  参考文献：
  名称：

  Antiproliferative activity of phenylbutyrate ester of haloperidol metabolite II [(±)-MRJF4] in prostate cancer cells

  摘要：

  Complex mechanisms of prostate cancer progression prompt to novel therapeutic strategies concerning a combination of drugs or of single molecules able to interact with more crucial targets. Histone deacetylase inhibitors and sigma ligands with mixed sigma(1) antagonist and sigma(2) agonist properties were proposed as new potential tools for treatment of prostate cancer. (+/-)-MRJF4 was synthesized as phenylbutyrate ester of haloperidol metabolite II, which is a molecule consisting of a histone deacetilase inhibitor (4-phenylbutyric acid) and a sigma ligand (haloperidol metabolite II). Antiproliferatives activities of 4-phenylbutyric acid, haloperidol metabolite II, equimolar mixture of both compounds and (+/-)-MRJF4 were evaluated in vitro on LNCaP and PO prostate cancer cells. Preliminary binding studies of (+/-)-MRJF4 for sigma(1), sigma(2), D-2 and D-3 receptors and inhibition HDAC activity were reported. KIT cell viability assays highlighted a notable increase of antiproliferative activity of (+/-)-MRJF4 (IC50 = 11 and 13 mu M for LNCaP and PC3, respectively) compared to 4-phenylbutyric acid, haloperidol metabolite II and the respective equimolar pharmacological association. (+/-)-MRJF4 was also used in combination with sigma(1) agonist (+)-pentazocine and sigma(2) antagonist AC927 in order to evaluate the role of sigma receptor subtypes in prostate cancer cell death. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.012