1-Benzyl-4-(3-methyl-5-phenyl-pyrazol-1-yl)-piperidine | 228874-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-Benzyl-4-(3-methyl-5-phenyl-pyrazol-1-yl)-piperidine
• 英文别名: 1-benzyl-4-(3-methyl-5-phenylpyrazol-1-yl)piperidine
• CAS: 228874-05-3
• 化学式: C₂₂H₂₅N₃
• 分子量: 331.461
• InChiKey: AHVVCJSEQJZGNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Benzyl-4-(3-methyl-5-phenyl-pyrazol-1-yl)-piperidine 在 palladium dihydroxide ammonium formate 、 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (R)-Cyclohexyl-{(3S,4S)-3-[4-(3-methyl-5-phenyl-pyrazol-1-yl)-piperidin-1-ylmethyl]-4-phenyl-pyrrolidin-1-yl}-acetic acid benzyl ester
  参考文献：
  名称：

  Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 1: Discovery and SAR study of 4-pyrazolylpiperidine side chains

  摘要：

  Replacement of the flexible connecting chains between the piperidine moiety and an aromatic group in previous CCR5 antagonists with heterocycles, such as pyrazole and isoxazole, provided potent CCR5 antagonists with excellent anti-HIV-1 activity in vitro. SAR studies revealed optimal placement of an unsubstituted nitrogen atom in the heterocycle to be meta to the bond connected to the 4-position of piperidine. Truncation of a benzyl group to a phenyl group afforded compounds with dramatically improved oral bioavailability, albeit with reduced activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.004
• 作为产物：
  描述：

  1-苯基-1,3-丁二酮 、 1-(1-苄基哌啶-4-基)肼 以 甲醇 为溶剂， 以73%的产率得到1-Benzyl-4-(3-methyl-5-phenyl-pyrazol-1-yl)-piperidine
  参考文献：
  名称：

  4-N-linked-heterocyclic piperidine derivatives with high affinity and selectivity for human dopamine D4 receptors

  摘要：

  The syntheses of a number of different N-linked heterocyclic pyrazole replacements based on the structure 1 are described (compounds 3-12) as hD4 ligands. After further optimisation the best compound identified was 13 which has high affinity for hD4 (5.2 nM) and >300-fold selectivity for hD4 receptors over hD2 and hD3 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00169-9