5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine | 1104467-53-9

• 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: 5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine
• 英文别名: 5-(2-morpholin-4-ylethoxy)-2-nitroaniline
• CAS: 1104467-53-9
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: AUXNHAZTDUTSHK-UHFFFAOYSA-N

物化性质

• 沸点：
  478.6±45.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-(2-吗啉-4-基乙氧基)苯-1,2-二胺
  参考文献：
  名称：

  Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors

  摘要：

  The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TK1258), are reversible ATP-competitive inhibitors of VEGFR-2, FGFR-1, and PDGFR beta with IC50 values <0.1 mu M. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.

  DOI：

  10.1021/jm800790t
• 作为产物：
  描述：

  2-吗啉乙醇 、 3-氨基-4-硝基苯酚 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine
  参考文献：
  名称：

  [EN] BENZIMIDAZOLE QUINOLINONES AND USES THEREOF
  [FR] QUINOLINONES DE BENZIMIDAZOLE ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2004018419A3

文献信息

• 吡唑类脾酪氨酸激酶抑制剂及其制备方法与用途
  申请人：中国药科大学

  公开号：CN112047932B

  公开（公告）日：2022-11-08

  本发明公开了一种吡唑类脾酪氨酸激酶抑制剂，并公开了其制备方法，本发明还公开了包含上述化合物的药物组合物，以及它们在制备治疗由Syk介导的疾病药物中的用途，所述疾病包括癌症和炎性疾病等。
• [EN] BENZIMIDAZOLE QUINOLINONES AND USES THEREOF<br/>[FR] QUINOLINONES DE BENZIMIDAZOLE ET LEURS UTILISATIONS
  申请人：CHIRON CORP

  公开号：WO2004018419A3

  公开（公告）日：2004-06-03
• Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors
  作者：Paul A. Renhowe、Sabina Pecchi、Cynthia M. Shafer、Timothy D. Machajewski、Elisa M. Jazan、Clarke Taylor、William Antonios-McCrea、Christopher M. McBride、Kelly Frazier、Marion Wiesmann、Gena R. Lapointe、Paul H. Feucht、Robert L. Warne、Carla C. Heise、Daniel Menezes、Kimberly Aardalen、Helen Ye、Molly He、Vincent Le、Jayesh Vora、Johanna M. Jansen、Mary Ellen Wernette-Hammond、Alex L. Harris

  DOI：10.1021/jm800790t

  日期：2009.1.22

  The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TK1258), are reversible ATP-competitive inhibitors of VEGFR-2, FGFR-1, and PDGFR beta with IC50 values <0.1 mu M. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.