5-methyl-N'-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]thiophene-2-carboximidamide | 1365320-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methyl-N'-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]thiophene-2-carboximidamide
• CAS: 1365320-73-5
• 化学式: C₂₀H₂₂N₄S
• 分子量: 350.487
• InChiKey: ADDLJEXSVRKASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-N'-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]thiophene-2-carboximidamide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.17h， 生成 5-methyl-N'-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]thiophene-2-carboximidamide;hydrochloride
  参考文献：
  名称：

  3,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase (nNOS) inhibitors

  摘要：

  A series of 3,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). Various guanidine isosteric groups were explored at the 5-position of the indole ring, while keeping the basic amine side chain such as N-methylpiperidine ring, fixed at the 3-position of the indole ring. Compounds having 2-thiophene amidine and 2-furanyl amidine groups (7, 8, 10 and 12) showed increased activity for human neuronal NOS and good selectivity over endothelial and inducible NOS isoforms. Compound 8 was shown to reverse (10 mg/kg, ip) thermal hyperalgesia in the L5/L6 spinal nerve ligation (neuropathic pain) model and was devoid of any significant drug-drug interaction potential due to cytochrome P450 inhibition or cardiovascular liabilities associated with the inhibition of endothelial NOS. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.031
• 作为产物：
  描述：

  3-(1-甲基-1,2,3,6-四氢吡啶-4-基)-5-硝基-1H-吲哚 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 5-methyl-N'-[3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indol-5-yl]thiophene-2-carboximidamide
  参考文献：
  名称：

  3,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase (nNOS) inhibitors

  摘要：

  A series of 3,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). Various guanidine isosteric groups were explored at the 5-position of the indole ring, while keeping the basic amine side chain such as N-methylpiperidine ring, fixed at the 3-position of the indole ring. Compounds having 2-thiophene amidine and 2-furanyl amidine groups (7, 8, 10 and 12) showed increased activity for human neuronal NOS and good selectivity over endothelial and inducible NOS isoforms. Compound 8 was shown to reverse (10 mg/kg, ip) thermal hyperalgesia in the L5/L6 spinal nerve ligation (neuropathic pain) model and was devoid of any significant drug-drug interaction potential due to cytochrome P450 inhibition or cardiovascular liabilities associated with the inhibition of endothelial NOS. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.031