4-chloro-6-(3-methoxyphenyl)pyrimidin-2-amine | 862168-12-5

• 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: 4-chloro-6-(3-methoxyphenyl)pyrimidin-2-amine
• CAS: 862168-12-5
• 化学式: C₁₁H₁₀ClN₃O
• 分子量: 235.673
• InChiKey: ULEVPPCKUXIGEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(3-methoxyphenyl)pyrimidin-2-amine 在 N,O-双三甲硅基乙酰胺 作用下， 以 正丁醇 为溶剂， 生成 2-Furan-2-yl-7-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-ylamine
  参考文献：
  名称：

  2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1

  摘要：

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.086
• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 、 3-甲氧基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-chloro-6-(3-methoxyphenyl)pyrimidin-2-amine
  参考文献：
  名称：

  2-(2-Furanyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine analogs: Highly potent, orally active, adenosine A2A antagonists. Part 1

  摘要：

  The structure-activity relationship of this novel class of compounds based on 2-(2-furanyl)-7-phenyl[1,2,4]-triazolo[1,5-c]pyrimidin-5-amine, 1, and its analogs was evaluated for their in vitro and in vivo adenosine A(2A) receptor antagonism. Several compounds displayed oral activity at 3 mg/kg in a rat catalepsy model. Specifically, compound 8g displayed an excellent in vitro profile, as well as a highly promising in vivo profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.086

文献信息

• Pyrimidine derivatives for treatment of hyperproliferative disorders
  申请人：Dixon A. Julie

  公开号：US20050277640A1

  公开（公告）日：2005-12-15

  Pyrimidine derivatives of formula (I) in which J and Y represent aromatic or heteroaromatic rings; R 2 , G, G′, and G″ represent substituent groups and R 2a represents H or halogen; L represents a linking group; and M represents CH or N. Pharmaceutical compositions containing these compounds, and methods of using these compounds in treatment of hyperproliferative diseases such as cancer are also disclosed and claimed.

  式(I)中的嘧啶衍生物，其中J和Y代表芳香环或杂芳环；R2、G、G′和G″代表取代基，而R2a代表氢或卤素；L代表连接基团；M代表CH或N。还公开和声明了含有这些化合物的药物组合物，并使用这些化合物治疗增殖过度性疾病，如癌症的方法。
• PYRIMIDINE DERIVATIVES FOR TREATMENT OF HYPERPROLIFERATIVE DISORDERS
  申请人：Dixon Julie A.

  公开号：US20100075967A1

  公开（公告）日：2010-03-25

  Pyrimidine derivatives of formula (I) in which J and Y represent aromatic or heteroaromatic rings; R 2 , G, G′, and G″ represent substituent groups and R 2a represents H or halogen; L represents a linking group; and M represents CH or N. Pharmaceutical compositions containing these compounds, and methods of using these compounds in treatment of hyperproliferative diseases such as cancer are also disclosed and claimed.

  公式（I）的嘧啶衍生物，其中J和Y代表芳香或杂芳环；R2，G，G'和G''代表取代基，R2a代表H或卤素；L代表连接基团；M代表CH或N。本发明还公开和声明了包含这些化合物的制药组合物，并使用这些化合物治疗高增殖性疾病，如癌症的方法。
• Pyrimidine Derivatives for Treatment of Hyperproliferative Disorders
  申请人：Dixon Julie A.

  公开号：US20110098301A1

  公开（公告）日：2011-04-28

  Pyrimidine derivatives of formula pharmaceutical compositions containing these compounds, and methods of using these compounds in treatment of hyperproliferative diseases such as cancer are disclosed and claimed.

  本发明揭示并声明了式的嘧啶衍生物、含有这些化合物的制药组合物以及使用这些化合物治疗癌症等增殖性疾病的方法。
• Discovery of Pyridinone Derivatives as Potent, Selective, and Orally Bioavailable Adenosine A_2A Receptor Antagonists for Cancer Immunotherapy
  作者：Chenyu Zhu、Shuyin Ze、Ronghui Zhou、Xinyu Yang、Haojie Wang、Xiaolei Chai、Meimiao Fang、Mingyao Liu、Yonghui Wang、Weiqiang Lu、Qiong Xie

  DOI：10.1021/acs.jmedchem.2c01860

  日期：——

  of adenosine A2A receptor (A2AR) antagonists as novel approaches for cancer immunotherapy. By screening our in-house compound library, a pyridinone hit compound (1) with weak A2AR antagonistic activity was identified. Further structure–activity relationship studies revealed a series of pyridinone derivatives with strong potency. Compound 38 stood out with a potent A2AR antagonistic activity (IC50 =

  最近的研究和临床证据强烈支持开发腺苷 A 2A受体 (A 2A R) 拮抗剂作为癌症免疫治疗的新方法。通过筛选我们的内部化合物库，鉴定出具有弱 A 2A R 拮抗活性的吡啶酮命中化合物 ( 1 ) 。进一步的构效关系研究揭示了一系列具有强大效力的吡啶酮衍生物。化合物38具有强大的 A 2A R 拮抗活性（IC 50 = 29.0 nM）、良好的小鼠肝微粒体代谢稳定性（t 1/2 = 86.1 分钟）和出色的口服生物利用度（F= 86.1%)。值得注意的是，38通过下调免疫抑制分子（LAG-3和TIM-3）和上调效应分子（GZMB、IFNG和IL-2）有效增强了体外 T 细胞的激活和杀伤能力。此外，38在 MC38 肿瘤模型中通过口服给药表现出优异的体内抗肿瘤活性，肿瘤生长抑制 (TGI) 为 56.0%，证明其作为癌症免疫治疗的新型 A 2A R 拮抗剂候选物的潜力。
• 4-AMINOPYRIMIDINE DERIVATIVES FOR TREATMENT OF HYPERPROLIFERATIVE DISORDERS
  申请人：Bayer Pharmaceuticals Corporation

  公开号：EP1689722A2

  公开（公告）日：2006-08-16