3-(4-cyclohexylpiperazin-1-yl)propan-1-ol methanesulphonate | 1335019-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-cyclohexylpiperazin-1-yl)propan-1-ol methanesulphonate
• 英文别名: 3-(4-Cyclohexylpiperazin-1-yl)propyl methanesulfonate
• CAS: 1335019-48-1
• 化学式: C₁₄H₂₈N₂O₃S
• 分子量: 304.454
• InChiKey: ZJEQTMJNPJWFGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-cyclohexylpiperazin-1-yl)propan-1-ol methanesulphonate 、 3,4-二氢异喹啉-1(2H)-酮 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 以45%的产率得到2-[3-(4-cyclohexylpiperazin-1-yl)propyl]-3,4-dihydroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Arylamides hybrids of two high-affinity σ2 receptor ligands as tools for the development of PET radiotracers

  摘要：

  1-Cyclohexy1-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) and 2-Methoxy-5-methyl-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl]benzamide 2 (RHM-1) represent leads for tumor diagnosis, given their high affinity at sigma(2) receptors. With the purpose of obtaining good candidates for sigma(2) PET tracers development, hybrid structures between 1 and 2 were designed. Excellent sigma(1)/sigma(2) selectivities were reached when 6,7-dimethoxytetrahydroisoquinoline was linked to an o-methoxy substituted arylamide (11a, 12a, 15a). and for these benzamides an intramolecular H-bond in the active conformation at the sigma sites, was hypothesized. However these excellent sigma(2) ligands were accompanied by interaction with P-gp. which may limit their use as sigma(2) receptor PET agents when tumors overexpress P-gp. Compound 15a whose P-gp interaction was just moderate represents an interesting tool for the development of sigma(2) PET tracers useful in tumors overexpressing P-gp. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.057
• 作为产物：
  描述：

  1-环己基哌嗪 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 3-(4-cyclohexylpiperazin-1-yl)propan-1-ol methanesulphonate
  参考文献：
  名称：

  Arylamides hybrids of two high-affinity σ2 receptor ligands as tools for the development of PET radiotracers

  摘要：

  1-Cyclohexy1-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine 1 (PB28) and 2-Methoxy-5-methyl-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)butyl]benzamide 2 (RHM-1) represent leads for tumor diagnosis, given their high affinity at sigma(2) receptors. With the purpose of obtaining good candidates for sigma(2) PET tracers development, hybrid structures between 1 and 2 were designed. Excellent sigma(1)/sigma(2) selectivities were reached when 6,7-dimethoxytetrahydroisoquinoline was linked to an o-methoxy substituted arylamide (11a, 12a, 15a). and for these benzamides an intramolecular H-bond in the active conformation at the sigma sites, was hypothesized. However these excellent sigma(2) ligands were accompanied by interaction with P-gp. which may limit their use as sigma(2) receptor PET agents when tumors overexpress P-gp. Compound 15a whose P-gp interaction was just moderate represents an interesting tool for the development of sigma(2) PET tracers useful in tumors overexpressing P-gp. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.057