N-(pyridin-4-yl)-3-(indol-3-yl)propionamide | 221637-03-2

• 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: N-(pyridin-4-yl)-3-(indol-3-yl)propionamide
• 英文别名: 3-(1H-indol-3-yl)-N-pyridin-4-ylpropanamide
• CAS: 221637-03-2
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: DSCUJKSYDNVTAX-UHFFFAOYSA-N

物化性质

• 沸点：
  582.7±35.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(pyridin-4-yl)-3-(indol-3-yl)propionamide 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 生成 ethyl N-[2-amino-6-[4-[3-(1H-indol-3-yl)propanoylamino]piperidin-1-yl]pyridin-3-yl]carbamate
  参考文献：
  名称：

  Fouchard; Marchand; Le Baut, Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 10, p. 814 - 824

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基吡啶 、 3-吲哚丙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到N-(pyridin-4-yl)-3-(indol-3-yl)propionamide
  参考文献：
  名称：

  Fouchard; Marchand; Le Baut, Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 10, p. 814 - 824

  摘要：

  DOI：

文献信息

• New N-pyridinyl(methyl)-indolalkanamides acting as topical inflammation inhibitors
  作者：Alexandra Dassonville、Anne Bretéché、Johan Evano、Muriel Duflos、Guillaume le Baut、Nicole Grimaud、Jean-Yves Petit

  DOI：10.1016/j.bmcl.2004.07.057

  日期：2004.11

  The authors have described the synthetic way to new N-pyridinyl(methyl)indolylpropanamides acting as non acidic NSAIDs. Pharmacomodulation was carried out at N-1 and C-5 of the indole ring and at the level of the propanamide chain. N-(pyridin-3-ylmethyl)-3-[5-chloro-1-(4-chlorobenzyl)-indol-3-yl]propanamide 32 represents one of the most potent compounds evaluated in the TPA-induced mouse ear swelling assay, with a level of activity higher than that of ibuprofen and comparable to that of dexamethasone. (C) 2004 Published by Elsevier Ltd.
• N-Pyridinyl-indole-3-(alkyl)carboxamides and derivatives as potential systemic and topical inflammation inhibitors
  作者：M Duflos

  DOI：10.1016/s0223-5234(01)01242-9

  日期：2001.6

  N-substituted-(indol-3-yl)carboxamides 10-15 and alkanamides 16-18 were prepared starting from the corresponding acids. and submitted to screening for evaluation of their anti-inflammatory activity. None of the considered carboxamides exhibited significant inhibitory effect in the carrageenin-induced rat paw oedema after oral administration of 0.1 mM kg(-1); nevertheless introduction of an alkyl chain, leading to alkanamides 16-18, induced moderate to high activity: 46-95% inhibition. The efficacy of these compounds in the inhibition of topical inflammation was confirmed by measuring reduction of ear thickness in the acute tetradecanoyl phorbol acetate (TPA)-induced mouse ear swelling assay. Preliminary pharmacomodulation brought to the fore that toxic effects induced, at 0.4 mM kg(-1), by N-(pyridin-4-yl)(indol-3-yl)propanamide (17) could be attenuated or suppressed by 5-fluorination or introduction of a methoxycarbonylborane moiety, leading to 18 and 21. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• Fouchard, Fabienne; Menciu, Cecilia; Duflos, Muriel, Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 96 - 105
  作者：Fouchard, Fabienne、Menciu, Cecilia、Duflos, Muriel、Baut, Guillaume Le、Lambrey, Bernard、Mourgues, Marie、Perrissoud, Daniel

  DOI：——

  日期：——
• Fouchard; Marchand; Le Baut, Arzneimittel-Forschung/Drug Research, 2001, vol. 51, # 10, p. 814 - 824
  作者：Fouchard、Marchand、Le Baut、Emig、Nickel

  DOI：——

  日期：——