N-(4,6-dimethylpyridin-2-yl)-5-bromofuran-2-carboxamide | 171370-47-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4,6-dimethylpyridin-2-yl)-5-bromofuran-2-carboxamide
• 英文别名: 5-bromo-N-(4,6-dimethylpyridin-2-yl)furan-2-carboxamide
• CAS: 171370-47-1
• 化学式: C₁₂H₁₁BrN₂O₂
• mdl: MFCD00438975
• 分子量: 295.136
• InChiKey: FUAPHHUJDLVHAG-UHFFFAOYSA-N

物化性质

• 沸点：
  316.4±42.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4,6-dimethylpyridin-2-yl)-5-bromofuran-2-carboxamide 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 0.17h， 以16%的产率得到5-bromo-N-(4,6-dimethylpyridin-2-yl)furan-2-carbothioamide
  参考文献：
  名称：

  Non-carboxylic antiinflammatory compounds. III. N-(4,6-Dimethylpyridin-2-yl)arylcarboxamides and arylthiocarboxamides acting as brain edema inhibitors

  摘要：

  Pharmacomodulation of the non-carboxylic NSAID N-(4,6-dimethylpyridin-2-yl)benzamide 1 led to the synthesis of structurally related furan, thiophene and pyrrole carboxamides 3-14. The derivatives benzenethiocarboxamides 15-18 and heteroaryl-thiocarboxamides 19-22 were also prepared by oxygen/sulfur exchange; this reaction was more efficiently carried out by P4S10 than by Lawesson's reagent. The 20 synthesized compounds were evaluated against peripheral edema by a foot-pad carrageenin-induced edema test. Amides 3-5, 8, 9, 11, 12 and 14 were most active, exhibiting > 90% inhibition after oral administration of 0.8 mmol . kg(-1). Two amides, 3 and 5, were selected for evaluation of their inhibitory activity in PLA(2)-induced brain edema and were found to be more potent than dexamethasone after LP administration.

  DOI：

  10.1016/0223-5234(96)88310-3
• 作为产物：
  描述：

  5-溴-2-糠酸 、 2-氨基-4,6-二甲基吡啶 在 四氯化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以55%的产率得到N-(4,6-dimethylpyridin-2-yl)-5-bromofuran-2-carboxamide
  参考文献：
  名称：

  Non-carboxylic antiinflammatory compounds. III. N-(4,6-Dimethylpyridin-2-yl)arylcarboxamides and arylthiocarboxamides acting as brain edema inhibitors

  摘要：

  Pharmacomodulation of the non-carboxylic NSAID N-(4,6-dimethylpyridin-2-yl)benzamide 1 led to the synthesis of structurally related furan, thiophene and pyrrole carboxamides 3-14. The derivatives benzenethiocarboxamides 15-18 and heteroaryl-thiocarboxamides 19-22 were also prepared by oxygen/sulfur exchange; this reaction was more efficiently carried out by P4S10 than by Lawesson's reagent. The 20 synthesized compounds were evaluated against peripheral edema by a foot-pad carrageenin-induced edema test. Amides 3-5, 8, 9, 11, 12 and 14 were most active, exhibiting > 90% inhibition after oral administration of 0.8 mmol . kg(-1). Two amides, 3 and 5, were selected for evaluation of their inhibitory activity in PLA(2)-induced brain edema and were found to be more potent than dexamethasone after LP administration.

  DOI：

  10.1016/0223-5234(96)88310-3

文献信息

• PHARMACEUTICAL COMBINATIONS
  申请人：Novartis AG

  公开号：EP1819361A2

  公开（公告）日：2007-08-22
• Pharmaceutical compositions
  申请人：Maibücher Axel

  公开号：US20070117833A1

  公开（公告）日：2007-05-24

  Pharmaceutical combinations comprising at least one mTOR inhibitor and their uses in treating arthritis or rheumatic arthritis and disorders associated therewith.
• [EN] PHARMACEUTICAL COMBINATIONS<br/>[FR] COMPOSITIONS PHARMACEUTIQUES
  申请人：NOVARTIS AG

  公开号：WO2005053661A2

  公开（公告）日：2005-06-16

  Pharmaceutical combinations comprising at least one mTOR inhibitor and their uses in treating arthritis or rheumatic arthritis and disorders associated therewith.
• Non-carboxylic antiinflammatory compounds. III. N-(4,6-Dimethylpyridin-2-yl)arylcarboxamides and arylthiocarboxamides acting as brain edema inhibitors
  作者：J.M.H. Robert、S Robert-Piessard、J Courant、G Le Baut、B Robert、F Lang、J.Y. Petit、N Grimaud、L Welin

  DOI：10.1016/0223-5234(96)88310-3

  日期：1995.1

  Pharmacomodulation of the non-carboxylic NSAID N-(4,6-dimethylpyridin-2-yl)benzamide 1 led to the synthesis of structurally related furan, thiophene and pyrrole carboxamides 3-14. The derivatives benzenethiocarboxamides 15-18 and heteroaryl-thiocarboxamides 19-22 were also prepared by oxygen/sulfur exchange; this reaction was more efficiently carried out by P4S10 than by Lawesson's reagent. The 20 synthesized compounds were evaluated against peripheral edema by a foot-pad carrageenin-induced edema test. Amides 3-5, 8, 9, 11, 12 and 14 were most active, exhibiting > 90% inhibition after oral administration of 0.8 mmol . kg(-1). Two amides, 3 and 5, were selected for evaluation of their inhibitory activity in PLA(2)-induced brain edema and were found to be more potent than dexamethasone after LP administration.