6-chloro-N-(2-hydroxyphenyl)hexanamide | 925698-73-3

• 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: 6-chloro-N-(2-hydroxyphenyl)hexanamide
• CAS: 925698-73-3
• 化学式: C₁₂H₁₆ClNO₂
• 分子量: 241.718
• InChiKey: LDCYAYVWXVZHLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-N-(2-hydroxyphenyl)hexanamide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(5-(4-(4-chlorophenyl)piperazin-1-yl)pentyl)benzo[d]oxazole
  参考文献：
  名称：

  Identification of a new selective dopamine D4 receptor ligand

  摘要：

  The dopamine D-4 receptor has been shown to play key roles in certain CNS pathologies including addiction to cigarette smoking. Thus, selective D-4 ligands may be useful in treating some of these conditions. Previous studies in our laboratory have indicated that the piperazine analog of haloperidol exhibits selective and increased affinity to the DAD(4) receptor subtype, in comparison to its piperidine analog. This led to further exploration of the piperazine moiety to identify new agents that are selective at the D-4 receptor. Compound 27 (KiD4 = 0.84 nM) was the most potent of the compounds tested. However, it only had moderate selectivity for the D-4 receptor. Compound 28 (KiD4 = 3.9 nM) while not as potent, was more discriminatory for the D-4 receptor subtype. In fact, compound 28 has little or no binding affinity to any of the other four DA receptor subtypes. In addition, of the 23 CNS receptors evaluated, only two, 5HT(1A)R and 5HT(2B)R, have binding affinity constants better than 100 nM (K-i < 100 nM). Compound 28 is a potentially useful D-4-selective ligand for probing disease treatments involving the D-4 receptor, such as assisting smoking cessation, reversing cognitive deficits in schizophrenia and treating erectile dysfunction. Thus, further optimization, functional characterization and evaluation in animal models may be warranted. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.04.026
• 作为产物：
  描述：

  6-氯己酰氯 、 2-氨基苯酚 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 6-chloro-N-(2-hydroxyphenyl)hexanamide
  参考文献：
  名称：

  Identification of a new selective dopamine D4 receptor ligand

  摘要：

  The dopamine D-4 receptor has been shown to play key roles in certain CNS pathologies including addiction to cigarette smoking. Thus, selective D-4 ligands may be useful in treating some of these conditions. Previous studies in our laboratory have indicated that the piperazine analog of haloperidol exhibits selective and increased affinity to the DAD(4) receptor subtype, in comparison to its piperidine analog. This led to further exploration of the piperazine moiety to identify new agents that are selective at the D-4 receptor. Compound 27 (KiD4 = 0.84 nM) was the most potent of the compounds tested. However, it only had moderate selectivity for the D-4 receptor. Compound 28 (KiD4 = 3.9 nM) while not as potent, was more discriminatory for the D-4 receptor subtype. In fact, compound 28 has little or no binding affinity to any of the other four DA receptor subtypes. In addition, of the 23 CNS receptors evaluated, only two, 5HT(1A)R and 5HT(2B)R, have binding affinity constants better than 100 nM (K-i < 100 nM). Compound 28 is a potentially useful D-4-selective ligand for probing disease treatments involving the D-4 receptor, such as assisting smoking cessation, reversing cognitive deficits in schizophrenia and treating erectile dysfunction. Thus, further optimization, functional characterization and evaluation in animal models may be warranted. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.04.026

文献信息

• XANTHINE DERIVATIVES AS SELECTIVE HM74A AGONISTS
  申请人：Hatley Richard Jonathan Daniel

  公开号：US20100179128A1

  公开（公告）日：2010-07-15

  The present invention relates to compounds of formula (I) which are xanthine derivatives, processes for the manufacture of said derivatives, pharmaceutical formulations containing these active compounds and the use of the compounds in therapy, for example, in the treatment of diseases where under-activation of the HM74A receptor contributes to the disease or where activation of the receptor will be beneficial

  本发明涉及式(I)的化合物，它们是黄嘌呤衍生物，制造这些衍生物的方法，含有这些活性化合物的制药配方，以及在治疗中使用这些化合物，例如，用于治疗HM74A受体欠活化导致疾病或激活该受体将有益的疾病。
• Identification of a new selective dopamine D4 receptor ligand
  作者：Dinithia Sampson、Xue Y. Zhu、Suresh V.K. Eyunni、Jagan R. Etukala、Edward Ofori、Barbara Bricker、Nazarius S. Lamango、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2014.04.026

  日期：2014.6

  The dopamine D-4 receptor has been shown to play key roles in certain CNS pathologies including addiction to cigarette smoking. Thus, selective D-4 ligands may be useful in treating some of these conditions. Previous studies in our laboratory have indicated that the piperazine analog of haloperidol exhibits selective and increased affinity to the DAD(4) receptor subtype, in comparison to its piperidine analog. This led to further exploration of the piperazine moiety to identify new agents that are selective at the D-4 receptor. Compound 27 (KiD4 = 0.84 nM) was the most potent of the compounds tested. However, it only had moderate selectivity for the D-4 receptor. Compound 28 (KiD4 = 3.9 nM) while not as potent, was more discriminatory for the D-4 receptor subtype. In fact, compound 28 has little or no binding affinity to any of the other four DA receptor subtypes. In addition, of the 23 CNS receptors evaluated, only two, 5HT(1A)R and 5HT(2B)R, have binding affinity constants better than 100 nM (K-i < 100 nM). Compound 28 is a potentially useful D-4-selective ligand for probing disease treatments involving the D-4 receptor, such as assisting smoking cessation, reversing cognitive deficits in schizophrenia and treating erectile dysfunction. Thus, further optimization, functional characterization and evaluation in animal models may be warranted. Published by Elsevier Ltd.