N-[(5-isobutyl-1-phenyl-1H-pyrazol-3-yl)methyl]benzenesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-[(5-isobutyl-1-phenyl-1H-pyrazol-3-yl)methyl]benzenesulfonamide
• 英文别名: N-[[5-(2-methylpropyl)-1-phenylpyrazol-3-yl]methyl]benzenesulfonamide
• 化学式: C₂₀H₂₃N₃O₂S
• 分子量: 369.488
• InChiKey: VVIHKCYUMFOOLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙基6-甲基-2,4-二氧亚基庚酯 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.58h， 生成 N-[(5-isobutyl-1-phenyl-1H-pyrazol-3-yl)methyl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and T-type calcium channel-blocking effects of aryl(1,5-disubstituted-pyrazol-3-yl)methyl sulfonamides for neuropathic pain treatment

  摘要：

  A novel series of aryl(1,5-disubstituted pyrazol-3-yl)methyl sulfonamide derivatives was designed, synthesized, and evaluated for T-type calcium channel (ctiG and chm) inhibitory activity. We identified several compounds, 9a, 9b, 9g, and 9h that displayed good T-type channel inhibitory potency with low hERG channel and CYP450 inhibition. Among them, 9a and 9b exhibited neuropathic pain alleviation effects in mechanical and cold allodynia induced in the SNL rat model. Compounds 9a and 9b displayed better efficacy than mibefradil and gabapentin against cold allodynia. In particular, compound 9a seemed to be valuable as shown fast acting performance in mechanical neuropathic pain model. (C) 2016 Elsevier Masson SAS. All rights reserved'.

  DOI：

  10.1016/j.ejmech.2016.07.032

文献信息

• COMPOUNDS CAPABLE OF INHIBITING VOLTAGE GATED CALCIUM ION CHANNEL, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20150329533A1

  公开（公告）日：2015-11-19

  Disclosed herein are an N-(pyrazolylmethyl)arylsulfonamide derivative useful as a calcium ion channel blocker, a pharmaceutically acceptable salt thereof, and the medicinal use thereof as a therapeutic agent using its calcium ion channel blocking effect.

  本文披露了一种N-(吡唑甲基)芳基磺酰胺衍生物，可用作钙离子通道阻滞剂，其药用盐，以及利用其钙离子通道阻滞效应作为治疗剂的药用。
• Neuropathic pain-alleviating effects of pyrazole-conjugated arylsulfonamides as 5-HT6 receptor antagonists
  作者：Jin Ri Hong、Hyunah Choo、Ghilsoo Nam

  DOI：10.1016/j.bmcl.2017.07.031

  日期：2017.9

  A novel series of arylsulfonylaminomethyl-3-(1-phenyl-5-isopropyl)pyrazoles was evaluated for serotonin receptor subtype 6 (5-HT6R) antagonistic effects in vitro. We also investigated their neuropathic pain-alleviating effects in vivo using a rat spinal nerve ligation (SNL) model. Bicyclic aromatic sulfonamino groups, such as naphthalene and quinolin-substituted derivatives, showed good 5-HT6 inhibitory activity in vitro. Among them, selected compounds, 12 and 13, having 8-quinoylsulfonamino groups, showed potent neuropathic pain-alleviating effects in the rat model. (C) 2017 Elsevier Ltd. All rights reserved.
• US9493423B2
  申请人：——

  公开号：US9493423B2

  公开（公告）日：2016-11-15
• Synthesis and T-type calcium channel-blocking effects of aryl(1,5-disubstituted-pyrazol-3-yl)methyl sulfonamides for neuropathic pain treatment
  作者：Jung Hyun Kim、Gyochang Keum、Hesson Chung、Ghilsoo Nam

  DOI：10.1016/j.ejmech.2016.07.032

  日期：2016.11

  A novel series of aryl(1,5-disubstituted pyrazol-3-yl)methyl sulfonamide derivatives was designed, synthesized, and evaluated for T-type calcium channel (ctiG and chm) inhibitory activity. We identified several compounds, 9a, 9b, 9g, and 9h that displayed good T-type channel inhibitory potency with low hERG channel and CYP450 inhibition. Among them, 9a and 9b exhibited neuropathic pain alleviation effects in mechanical and cold allodynia induced in the SNL rat model. Compounds 9a and 9b displayed better efficacy than mibefradil and gabapentin against cold allodynia. In particular, compound 9a seemed to be valuable as shown fast acting performance in mechanical neuropathic pain model. (C) 2016 Elsevier Masson SAS. All rights reserved'.