3-iodo-6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine | 709631-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-iodo-6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine
• CAS: 709631-61-8
• 化学式: C₁₃H₁₀IN₃O
• 分子量: 351.146
• InChiKey: VJLHKOKZHWKZNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-iodo-6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6-(4-methoxyphenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe

  摘要：

  A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a] pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.113
• 作为产物：
  描述：

  6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-iodo-6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe

  摘要：

  A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a] pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents were evaluated with subtle structural changes leading to significant changes in potency. From these studies, a novel 5-quinoline molecule was identified and designated an MLPCN probe molecule, ML347, which shows >300-fold selectivity for ALK2 and presents the community with a selective molecular probe for further biological evaluation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.113

文献信息

• Tyrosine kinase inhibitors
  申请人：Fraley E. Mark

  公开号：US20060025426A1

  公开（公告）日：2006-02-02

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, macular edema, retinal ischemia, inflammatory diseases, and the like in mammals.

  本发明涉及抑制、调节和/或调节酪氨酸激酶信号传导的化合物，包含这些化合物的组合物，以及使用它们治疗哺乳动物中的酪氨酸激酶依赖性疾病和病状的方法，例如血管生成、癌症、肿瘤生长、动脉硬化、年龄相关性黄斑变性、糖尿病视网膜病变、黄斑水肿、视网膜缺血、炎症性疾病等。
• Substituted pyrazolo[1,5-A]pyrimidines as tyrosine kinase inhibitors
  申请人：Merck & Co. Inc.

  公开号：US07550470B2

  公开（公告）日：2009-06-23

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, macular edema, retinal ischemia, inflammatory diseases, and the like in mammals.

  本发明涉及抑制、调节和/或调节酪氨酸激酶信号转导的化合物，包含这些化合物的组合物以及使用它们治疗哺乳动物的酪氨酸激酶依赖性疾病和病状的方法，例如血管生成、癌症、肿瘤生长、动脉硬化、老年性黄斑变性、糖尿病性视网膜病变、黄斑水肿、视网膜缺血、炎症性疾病等。
• US7550470B2
  申请人：——

  公开号：US7550470B2

  公开（公告）日：2009-06-23
• [EN] TYROSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DES TYROSINE KINASES
  申请人：MERCK & CO INC

  公开号：WO2004052315A2

  公开（公告）日：2004-06-24

  The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, macular edema, retinal ischemia, inflammatory diseases, and the like in mammals.