Methyl 3-[(2-cyanoacetyl)amino]-4-methylbenzoate | 1314804-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-[(2-cyanoacetyl)amino]-4-methylbenzoate
• 英文别名: methyl 3-[(2-cyanoacetyl)amino]-4-methylbenzoate
• CAS: 1314804-47-1
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: BZUFBIOBBYRSGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.19
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(2-cyanoacetyl)amino]-4-methylbenzoate 在 N-氯代丁二酰亚胺 、 sodium methylate 、 potassium carbonate 、 二硫代磷酸二乙酯 作用下， 以 1,4-二氧六环 、 水 、 异丙醇 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  Substituted N -aryl-6-pyrimidinones: A new class of potent, selective, and orally active p38 MAP kinase inhibitors

  摘要：

  A novel series of highly potent and selective p38 MAP kinase inhibitors was developed originating from a substituted N-aryl-6-pyrimidinone scaffold. SAR studies coupled with in vivo evaluations in rat arthritis model culminated in the identification of 10 with excellent oral efficacy. Compound 10 exhibited a significantly enhanced dissolution rate compared to 1, translating to a high oral bioavailability (> 90%) in rat. In animal studies 10 inhibited LPS-stimulated production of tumor necrosis factor-alpha in a dose-dependent manner and demonstrated robust efficacy comparable to dexamethasone in a rat streptococcal cell wall-induced arthritis model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.006
• 作为产物：
  描述：

  3-氨基-4-甲基苯甲酸甲酯 、 氰乙酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以42%的产率得到Methyl 3-[(2-cyanoacetyl)amino]-4-methylbenzoate
  参考文献：
  名称：

  Substituted N -aryl-6-pyrimidinones: A new class of potent, selective, and orally active p38 MAP kinase inhibitors

  摘要：

  A novel series of highly potent and selective p38 MAP kinase inhibitors was developed originating from a substituted N-aryl-6-pyrimidinone scaffold. SAR studies coupled with in vivo evaluations in rat arthritis model culminated in the identification of 10 with excellent oral efficacy. Compound 10 exhibited a significantly enhanced dissolution rate compared to 1, translating to a high oral bioavailability (> 90%) in rat. In animal studies 10 inhibited LPS-stimulated production of tumor necrosis factor-alpha in a dose-dependent manner and demonstrated robust efficacy comparable to dexamethasone in a rat streptococcal cell wall-induced arthritis model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.006