[4-(cyclopropylamino)piperidin-1-yl][5-fluoro-2-(methylsulfonyl)phenyl]methanone | 1409937-61-6

• 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-(cyclopropylamino)piperidin-1-yl][5-fluoro-2-(methylsulfonyl)phenyl]methanone
• 英文别名: [4-(Cyclopropylamino)piperidin-1-yl]-(5-fluoro-2-methylsulfonylphenyl)methanone；[4-(cyclopropylamino)piperidin-1-yl]-(5-fluoro-2-methylsulfonylphenyl)methanone
• CAS: 1409937-61-6
• 化学式: C₁₆H₂₁FN₂O₃S
• 分子量: 340.419
• InChiKey: XEQUQPSQHUMQJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-(cyclopropylamino)piperidin-1-yl][5-fluoro-2-(methylsulfonyl)phenyl]methanone 、 2-三氟甲基苯磺酰氯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 生成 N-cyclopropyl-N-[1-(5-fluoro-2-methylsulfonylbenzoyl)piperidin-4-yl]-2-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Aminopiperidine Sulfonamide Ca_v2.2 Channel Inhibitors for the Treatment of Chronic Pain

  摘要：

  The voltage-gated calcium channel Ca(v)2.2 (N-type calcium channel) is a critical regulator of Synaptic transmission and has emerged as an attractive target for the treatment of chronic pain. We report here the discovery. of sulfonamide derived, state-dependent inhibitors of Ca(v)2.2. In particular,. 19 is an inhibitor of Ca(v)2.2 that is selective over cardiac ion channels, with a good preclinical PK and biodistribution profile. This compound exhibits dose dependent. efficacy in preclinical Models of inflammatory hyperalgesia and neuropathic allodynia and is devoid of ancillary cardiovascular or CNS pharmacology at the doses tested. Importantly, 19 exhibited no efficacy in Ca(v)2.2 gene-deleted mice. The discovery of metabolite 26 confounds further development of members. of this aminopiperidine sulfonamide series. This discovery also Suggests specific structural-liabilities of this class of compounds that Must be addressed.

  DOI：

  10.1021/jm301056k
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 [4-(cyclopropylamino)piperidin-1-yl][5-fluoro-2-(methylsulfonyl)phenyl]methanone
  参考文献：
  名称：

  Aminopiperidine Sulfonamide Ca_v2.2 Channel Inhibitors for the Treatment of Chronic Pain

  摘要：

  The voltage-gated calcium channel Ca(v)2.2 (N-type calcium channel) is a critical regulator of Synaptic transmission and has emerged as an attractive target for the treatment of chronic pain. We report here the discovery. of sulfonamide derived, state-dependent inhibitors of Ca(v)2.2. In particular,. 19 is an inhibitor of Ca(v)2.2 that is selective over cardiac ion channels, with a good preclinical PK and biodistribution profile. This compound exhibits dose dependent. efficacy in preclinical Models of inflammatory hyperalgesia and neuropathic allodynia and is devoid of ancillary cardiovascular or CNS pharmacology at the doses tested. Importantly, 19 exhibited no efficacy in Ca(v)2.2 gene-deleted mice. The discovery of metabolite 26 confounds further development of members. of this aminopiperidine sulfonamide series. This discovery also Suggests specific structural-liabilities of this class of compounds that Must be addressed.

  DOI：

  10.1021/jm301056k