(R)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine | 1021918-52-4

• 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: (R)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine
• 英文别名: (R)-6-Bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine；5-bromo-6-methyl-3-N-[(1R)-1-phenylethyl]pyrazine-2,3-diamine
• CAS: 1021918-52-4
• 化学式: C₁₃H₁₅BrN₄
• 分子量: 307.193
• InChiKey: HHAXDICFEPKZFC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 、 caesium carbonate 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 13.0h， 生成 3-[5-amino-3-methyl-6-[[(1R)-1-phenylethyl]amino]pyrazin-2-yl]benzoic acid
  参考文献：
  名称：

  Identification of 2-amino-5-aryl-pyrazines as inhibitors of human lactate dehydrogenase

  摘要：

  A 2-amino-5-aryl-pyrazine was identified as an inhibitor of human lactate dehydrogenase A (LDHA) via a biochemical screening campaign. Biochemical and biophysical experiments demonstrated that the compound specifically interacted with human LDHA. Structural variation of the screening hit resulted in improvements in LDHA biochemical inhibition and pharmacokinetic properties. A crystal structure of an improved compound bound to human LDHA was also obtained and it explained many of the observed structure-activity relationships. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.060
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 N,N-二异丙基乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 正丁醇 为溶剂， 反应 3.0h， 生成 (R)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine
  参考文献：
  名称：

  Identification of 2-amino-5-aryl-pyrazines as inhibitors of human lactate dehydrogenase

  摘要：

  A 2-amino-5-aryl-pyrazine was identified as an inhibitor of human lactate dehydrogenase A (LDHA) via a biochemical screening campaign. Biochemical and biophysical experiments demonstrated that the compound specifically interacted with human LDHA. Structural variation of the screening hit resulted in improvements in LDHA biochemical inhibition and pharmacokinetic properties. A crystal structure of an improved compound bound to human LDHA was also obtained and it explained many of the observed structure-activity relationships. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.060

文献信息

• Heteroaryl compounds, compositions thereof, and methods of treatment therewith
  申请人：Mortensen Deborah Sue

  公开号：US20090023724A1

  公开（公告）日：2009-01-22

  Provided herein are Heteroaryl Compounds having the following structure: wherein R 1 , R 2 , L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

  本文提供具有以下结构的杂环芳基化合物：其中R1，R2，L，X，Y，Z，Q，A和B的定义如下，包括有效量的杂环芳基化合物的组合物以及治疗或预防癌症，炎症状况，免疫状况，代谢状况以及通过抑制激酶通路可治疗或预防的状况的方法，包括向需要治疗的患者中给予有效量的杂环芳基化合物。
• METHODS OF TREATMENT COMPRISING THE ADMINISTRATION OF HETEROARYL COMPOUNDS
  申请人：Mortensen Deborah Sue

  公开号：US20110245245A1

  公开（公告）日：2011-10-06

  Provided herein are Heteroaryl Compounds having the following structure: wherein R 1 , R 2 , L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

  本文提供了具有以下结构的杂环芳基化合物：其中R1、R2、L、X、Y、Z、Q、A和B的定义如下，包括有效量的杂环芳基化合物的组合物，并且治疗或预防癌症、炎症状况、免疫病状况、代谢病状况和通过抑制激酶途径可治疗或预防的病状况的方法包括向需要治疗的患者中施用有效量的杂环芳基化合物。
• Methods of treatment comprising the administration of heteroaryl compounds
  申请人：Mortensen Deborah Sue

  公开号：US08372976B2

  公开（公告）日：2013-02-12

  Provided herein are Heteroaryl Compounds having the following structure: wherein R1, R2, L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

  本文提供具有以下结构的杂环芳基化合物：其中R1、R2、L、X、Y、Z、Q、A和B的定义如下，包括有效量的杂环芳基化合物的组合物以及治疗或预防癌症、炎症疾病、免疫疾病、代谢疾病以及通过抑制激酶通路治疗或预防的疾病的方法，包括向需要的患者投与有效量的杂环芳基化合物。
• HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND METHODS OF TREATMENT THEREWITH
  申请人：Signal Pharmaceuticals LLC

  公开号：EP2078016A2

  公开（公告）日：2009-07-15
• Heteroaryl compounds, compositions thereof, and their use as protein kinase inhibitors
  申请人：Signal Pharmaceuticals, LLC

  公开号：EP2090577B1

  公开（公告）日：2017-04-05