1-氨基-3-(2-氟-5-甲基苯基)脲 | 918824-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-氨基-3-(2-氟-5-甲基苯基)脲
• 英文名称: N-(2-Fluoro-5-methylphenyl)hydrazinecarboxamide
• 英文别名: 1-amino-3-(2-fluoro-5-methylphenyl)urea
• CAS: 918824-71-2
• 化学式: C₈H₁₀FN₃O
• 分子量: 183.185
• InChiKey: OTFDVHNGSFLRGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-氨基-3-(2-氟-5-甲基苯基)脲 在 potassium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 42.0h， 生成 5-ethyl-N-(2-fluoro-5-methylphenyl)-3-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide
  参考文献：
  名称：

  Discovery of novel tetrahydro-pyrazolo [4,3-c] pyridines for the treatment of neuropathic pain: Synthesis and neuropharmacology

  摘要：

  We disclose the discovery of a novel series of tetrahydropyrido-pyrazoles that are potent inhibitors of tumour necrosis factor-alpha (TNF-alpha), nitric oxide and cannabinoid receptor subtype 1 (CBI). We report herein the synthesis and neuropharmacological screening results of the titled compounds in two acute pain and two neuropathic pain models in rodents. Particularly the analogue N-(4-bromophenyl)-3-tertbutyl-5-ethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide (8a) exhibited pronounced acute antinociceptive efficacy, also being effective in chronic constriction injury (ED50 = 23.8 mg/kg) and partial sciatic nerve injury (ED50 = 29.0 mg/kg) models with CB receptor activity (IC50 = 49.6 nM) and inhibitory effect on TNF-alpha (86.4% inhibition at 100 mg/kg). These results suggest the importance of the development of this lead as multi-targeted treatment strategy for neuropathic pain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.022

文献信息

• Discovery of novel tetrahydro-pyrazolo [4,3-c] pyridines for the treatment of neuropathic pain: Synthesis and neuropharmacology
  作者：Perumal Yogeeswari、Monika Sharma、Ganesh Samala、Matharasala Gangadhar、Srirama Karthick、Saketh Mallipeddi、Arvind Semwal、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2013.05.022

  日期：2013.8

  We disclose the discovery of a novel series of tetrahydropyrido-pyrazoles that are potent inhibitors of tumour necrosis factor-alpha (TNF-alpha), nitric oxide and cannabinoid receptor subtype 1 (CBI). We report herein the synthesis and neuropharmacological screening results of the titled compounds in two acute pain and two neuropathic pain models in rodents. Particularly the analogue N-(4-bromophenyl)-3-tertbutyl-5-ethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-1-carboxamide (8a) exhibited pronounced acute antinociceptive efficacy, also being effective in chronic constriction injury (ED50 = 23.8 mg/kg) and partial sciatic nerve injury (ED50 = 29.0 mg/kg) models with CB receptor activity (IC50 = 49.6 nM) and inhibitory effect on TNF-alpha (86.4% inhibition at 100 mg/kg). These results suggest the importance of the development of this lead as multi-targeted treatment strategy for neuropathic pain. (C) 2013 Elsevier Masson SAS. All rights reserved.