5-chloro-N-{2-[(2-hydroxyethyl)phenylamino]-2-oxoethyl}-1H-indole-2-carboxamide

• 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: 5-chloro-N-{2-[(2-hydroxyethyl)phenylamino]-2-oxoethyl}-1H-indole-2-carboxamide
• 英文别名: 5-chloro-N-[2-[N-(2-hydroxyethyl)anilino]-2-oxoethyl]-1H-indole-2-carboxamide
• 化学式: C₁₉H₁₈ClN₃O₃
• 分子量: 371.823
• InChiKey: YAFZVFCDUNEXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氯吲哚-2-羧酸氯 在 盐酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 5-chloro-N-{2-[(2-hydroxyethyl)phenylamino]-2-oxoethyl}-1H-indole-2-carboxamide
  参考文献：
  名称：

  5-Chloroindoloyl glycine amide inhibitors of glycogen phosphorylase: synthesis, in vitro, in vivo, and X-ray crystallographic characterization

  摘要：

  The synthesis, in vitro, and in vivo biological characterization of a series of achiral 5-chloroindoloyl glycine amide inhibitors of human liver glycogen phosphorylase A are described. Improved potency over previously reported compounds in cellular and in vivo assays was observed. The allosteric binding site of these compounds was shown by X-ray crystallography to be the same as that reported previously for 5-chloroindoloyl norstatine amides.

  DOI：

  10.1016/j.bmcl.2004.10.048

文献信息

• Chemical compounds
  申请人：Morley David Andrew

  公开号：US20050159472A1

  公开（公告）日：2005-07-21

  Heterocyclic amides of formula (1) wherein: R 1 is independently selected from, for example, C 1-6 alkyl, C 5-7 cycloalkyl, C 5-7 cycloalkylC 1-3 alkyl, C 1-6 alkoxy, C 5-7 cycloalkoxy, C 5-7 cycloalkylC 1-3 alkoxy, heterocyclyl, heterocyclylC 1-3 alkyl, heterocyclyloxy or heterocyclylC 1-3 alkoxy, R 2 is phenyl or heteroaryl; R 3 is independently selected from hydrogen, halo, nitro, cyano, hydroxy, carboxy, carbamoyl, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkyl, C 1-4 alkoxy, C 1-4 alkanoyl, fluoromethyl, difluoromethyl trifluoromethyl and trifluoromethoxy; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  式（1）的杂环酰胺，其中：R1独立地选择自C1-6烷基、C5-7环烷基、C5-7环烷基C1-3烷基、C1-6烷氧基、C5-7环烷氧基、C5-7环烷基C1-3烷氧基、杂环基、杂环基C1-3烷基、杂环氧基或杂环基C1-3烷氧基；R2为苯基或杂环芳基；R3独立地选择自氢、卤素、硝基、氰基、羟基、羧基、氨基甲酰、C1-4烷基、C2-4烯基、C2-4烷基、C1-4烷氧基、C1-4酰基、氟甲基、二氟甲基、三氟甲基和三氟甲氧基；或其药学上可接受的盐或前药。该化合物具有糖原磷酸化酶抑制活性，因此在治疗与糖原磷酸化酶活性增加相关的疾病状态中具有价值。描述了制备该杂环酰胺衍生物和含有它们的制药组合物的工艺。
• Indole-amide derivatives and their use as glycogen phosphorylase inhibitors
  申请人：AstraZeneca AB

  公开号：US07115648B2

  公开（公告）日：2006-10-03

  Heterocyclic amides of formula (1) wherein: R1 is independently selected from, for example, C1-6alkyl, C5-7cycloalkyl, C5-7cycloalkylC1-3alkyl, C1-6alkoxy, C5-7cycloalkoxy, C5-7cycloalkylC1-3alkoxy, heterocyclyl, heterocyclylC1-3alkyl, heterocyclyloxy or heterocyclylC1-3alkoxy, R2 is phenyl or heteroaryl; R3 is independently selected from hydrogen, halo, nitro, cyano, hydroxy, carboxy, carbamoyl, C1-4alkyl, C2-4alkenyl, C2-4alkyl, C1-4alkoxy, C1-4alkanoyl, fluoromethyl, difluoromethyl trifluoromethyl and trifluoromethoxy; or a pharmaceutically acceptable salt or pro-drug thereof; possess glycogen phosphorylase inhibitory activity and accordingly have value in the treatment of disease states associated with increased glycogen phosphorylase activity. Processes for the manufacture of said heterocyclic amide derivatives and pharmaceutical compositions containing them are described.

  式（1）的杂环酰胺，其中：R1独立地选自C1-6烷基，C5-7环烷基，C5-7环烷基C1-3烷基，C1-6烷氧基，C5-7环烷氧基，C5-7环烷基C1-3烷氧基，杂环基，杂环基C1-3烷基，杂环氧基或杂环基C1-3烷氧基；R2为苯基或杂环芳基；R3独立地选自氢，卤素，硝基，氰基，羟基，羧基，氨基甲酰基，C1-4烷基，C2-4烯基，C2-4烷基，C1-4烷氧基，C1-4酰基，氟甲基，二氟甲基，三氟甲基和三氟甲氧基；或其药学上可接受的盐或前药。具有糖原磷酸化酶抑制活性，因此对治疗与增加的糖原磷酸化酶活性相关的疾病状态具有价值。描述了制造该杂环酰胺衍生物和含有它们的制药组合物的过程。
• [EN] INDOLE-AMIDE DERIVATIVES AND THEIR USE AS GLYCOGEN PHOSPHORYLASE INHIBITORS<br/>[FR] COMPOSES CHIMIQUES
  申请人：——

  公开号：WO2003074485A3

  公开（公告）日：2003-12-04
• INDOLE-AMIDE DERIVATIVES AND THEIR USE AS GLYCOGEN PHOSPHORYLASE INHIBITORS
  申请人：Astrazeneca AB

  公开号：EP1483239A2

  公开（公告）日：2004-12-08
• US7115648B2
  申请人：——

  公开号：US7115648B2

  公开（公告）日：2006-10-03