4-Amino-3-cyano-6-[(4-methylsulfonylphenyl)methylcarbamoyl]pyridine-2-carboxylic acid | 904312-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-Amino-3-cyano-6-[(4-methylsulfonylphenyl)methylcarbamoyl]pyridine-2-carboxylic acid
• CAS: 904312-66-9
• 化学式: C₁₆H₁₄N₄O₅S
• 分子量: 374.377
• InChiKey: PEQNQKFMQQMMDF-UHFFFAOYSA-N

物化性质

• 沸点：
  747.9±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-Amino-3-cyano-6-[(4-methylsulfonylphenyl)methylcarbamoyl]pyridine-2-carboxylic acid 、 异丙胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到N6-(4-(methylsulfonyl)benzyl)-4-amino-3-cyano-N2-isopropylpyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Aminopyridine carboxamides as c-Jun N-terminal kinase inhibitors: Targeting the gatekeeper residue and beyond

  摘要：

  The structure-activity relationships of 5,6-positions of aminopyridine carboxamide-based c-Jun N-terminal Kinase (JNK) inhibitors were explored to expand interaction with the kinase specificity and ribose-binding pockets. The syntheses of analogues and the impact of structural modification on in vitro potency and cellular activity are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.097
• 作为产物：
  描述：

  trifluoromethanesulfonic acid 4-amino-6-chloro-5-cyanopyridin-2-yl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide 、 sodium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、413.68 kPa 条件下， 反应 32.0h， 生成 4-Amino-3-cyano-6-[(4-methylsulfonylphenyl)methylcarbamoyl]pyridine-2-carboxylic acid
  参考文献：
  名称：

  Aminopyridine carboxamides as c-Jun N-terminal kinase inhibitors: Targeting the gatekeeper residue and beyond

  摘要：

  The structure-activity relationships of 5,6-positions of aminopyridine carboxamide-based c-Jun N-terminal Kinase (JNK) inhibitors were explored to expand interaction with the kinase specificity and ribose-binding pockets. The syntheses of analogues and the impact of structural modification on in vitro potency and cellular activity are described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.097

文献信息

• Inhibitors of c-Jun N-terminal kinases
  申请人：Liu Gang

  公开号：US20060173050A1

  公开（公告）日：2006-08-03

  The present invention relates to compounds that are inhibitors of c-jun N-terminal kinase 1, 2, or 3 (JNK1, JNK2, or JNK3), compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the activation of JNK1, JNK2 and JNK3.

  本发明涉及作为c-jun N-末端激酶1、2或3（JNK1、JNK2或JNK3）抑制剂的化合物，包含这些化合物的组合物以及这些化合物在预防或治疗由JNK1、JNK2和JNK3激活调控的疾病中的用途。
• US7888374B2
  申请人：——

  公开号：US7888374B2

  公开（公告）日：2011-02-15
• [EN] INHIBITORS OF C-JUN N-TERMINAL KINASES<br/>[FR] INHIBITEURS DES C-JUN N-TERMINAL KINASES
  申请人：ABBOTT LAB

  公开号：WO2006083673A2

  公开（公告）日：2006-08-10

  [EN] The present invention relates to compounds that are inhibitors of c-jun N-terminal kinase 1, 2, or 3 (JNK1, JNK2, or JNK3), compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the activation of JNK1, JNK2 and JNK3.
  [FR] L'invention porte sur des composés qui sont des inhibiteurs de la c-jun N-terminal kinase 1, 2 ou 3 (JNK1, JNK2, ou JNK3), sur des compositions contenant lesdits composés et sur l'utilisation des composés dans la prévention ou le traitement des troubles régulés par l'activation de JNK1, JNK2 et JNK3.
• Aminopyridine carboxamides as c-Jun N-terminal kinase inhibitors: Targeting the gatekeeper residue and beyond
  作者：Gang Liu、Hongyu Zhao、Bo Liu、Zhili Xin、Mei Liu、Christi Kosogof、Bruce G. Szczepankiewicz、Sanyi Wang、Jill E. Clampit、Rebecca J. Gum、Deanna L. Haasch、James M. Trevillyan、Hing L. Sham

  DOI：10.1016/j.bmcl.2006.08.097

  日期：2006.11

  The structure-activity relationships of 5,6-positions of aminopyridine carboxamide-based c-Jun N-terminal Kinase (JNK) inhibitors were explored to expand interaction with the kinase specificity and ribose-binding pockets. The syntheses of analogues and the impact of structural modification on in vitro potency and cellular activity are described. (c) 2006 Elsevier Ltd. All rights reserved.