1,3-dimethyl-8-(morpholin-4-yl)-7-[3-(4-phenylpiperazin-1-yl)propyl]-3,7-dihydropurine-2,6-dione hydrochloride | 1609199-59-8

• 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: 1,3-dimethyl-8-(morpholin-4-yl)-7-[3-(4-phenylpiperazin-1-yl)propyl]-3,7-dihydropurine-2,6-dione hydrochloride
• CAS: 1609199-59-8
• 化学式: C₂₄H₃₃N₇O₃*ClH
• 分子量: 504.032
• InChiKey: WLEGWUCWJAZMEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  80.77
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  7-(3-chloropropyl)-1,3-dimethyl-8-morpholin-4-yl-3,7-dihydropurine-2,6-dione 、 N-苯基哌嗪 在 potassium carbonate 、 盐酸 作用下， 以 丙醇 、 丙酮 为溶剂， 反应 30.0h， 以62%的产率得到1,3-dimethyl-8-(morpholin-4-yl)-7-[3-(4-phenylpiperazin-1-yl)propyl]-3,7-dihydropurine-2,6-dione hydrochloride
  参考文献：
  名称：

  New 7-arylpiperazinylalkyl-8-morpholin-4-yl-purine-2,6-dione derivatives with anxiolytic activity – Synthesis, crystal structure and structure–activity study

  摘要：

  On the basis of our earlier studies with serotonin (5-HT) receptor ligands in the group of long-chain arylpiperazines (LCAPs), a new series of 7-arylpiperazinylalkyl-8-morpholin-4-yl-purine-2,6-dione derivatives (5-12) has been designed, synthesised and studied in vitro for their affinity for 5-HT1A, 5-HT2A, 5-HT6 and 5-HT7 receptors. The introduction of o-OCH3 and m-Cl into the phenylpiperazinyl moiety as well as the elongation of the linker between purine-2,6-dione core and arylpiperazine fragment modified the affinity for the tested 5-HT receptors. The structures of compounds 9-11 (hydrochloride salts) were confirmed by an X-ray diffraction method. All molecules adopted a different conformation in the crystal. The strongest observed type of interaction is a charge assisted hydrogen bond N+-H center dot center dot center dot Cl-. Additionally, the pi-pi interactions between 1,3-dimethyl-3,7-dihydropurine-2,6-dione cores of the neighbouring molecules were also observed. As it is observed in the presented crystal structures, the morpholine ring (a potential donor and acceptor of the hydrogen bonds) seems to be an attractive substituent, that may support binding to the non-specific sites of 5-HT receptors. Another interesting feature is the mutual orientation of rings in the arylpiperazine fragment, with plausible influence on ligand-receptor recognition. For compound 10, with strong 5-HT,A binding affinity, the mutual orientation of rings is determined by the intramolecular weak C-H center dot center dot center dot O hydrogen bond. This observation may contribute to a better understanding of the more selective binding of o-OCH3 arylpiperazine derivatives to the 5-HT1A receptor. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.03.018