2-chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine
• 英文别名: 2-Chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine
• 化学式: C₁₂H₁₁ClN₄O₃
• 分子量: 294.697
• InChiKey: WRQSXWSOOBHEIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine 在 盐酸 、 氢气 、 镍 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙二醇甲醚 、 水 为溶剂， 反应 4.0h， 生成 3-(4-ethoxyphenyl)-N-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]triazolo[4,5-d]pyrimidin-5-amine
  参考文献：
  名称：

  Biochemical, cellular and structural characterization of novel and selective ERK3 inhibitors

  摘要：

  Triazolo[4,5-d]pyrimidin-5-amines were identified from kinase selectivity screening as novel ERK3 inhibitors with sub-100 nanomolar potencies in a biochemical assay using MK5 as substrate and with an attractive kinase selectivity profile. ERK3 crystal structures clarified the inhibitor binding mode in the ATP pocket with impact on A-loop, GC-loop and αC-helix conformations suggesting a potential structural link towards MK5 interaction via the FHIEDE motif. The inhibitors also showed sub-100 nM potencies in a cellular ERK3 NanoBRET assay and with excellent correlation to the biochemical IC₅₀s. This novel series provides valuable tool compounds to further investigate the biological function and activation mechanism of ERK3.

  DOI：

  10.1016/j.bmcl.2020.127551
• 作为产物：
  描述：

  对乙氧基苯胺 、 2,4-二氯-5 硝基嘧啶 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以to give the 2-chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine的产率得到2-chloro-N-(4-ethoxyphenyl)-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  IMIDAZOPYRIMIDINE DERIVATIVES

  摘要：

  公式I中的化合物，其中X，R1和R2具有声明1中指定的含义，是GCN2的抑制剂，可用于治疗癌症等方面。

  公开号：

  US20160002242A1

文献信息

• 9-(ARYL OR HETEROARYL)-2-(PYRAZOLYL, PYRROLIDINYL OR CYCLOPENTYL)AMINOPURINE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Merck Patent GmbH

  公开号：EP2964648B1

  公开（公告）日：2016-11-16
• US9617266B2
  申请人：——

  公开号：US9617266B2

  公开（公告）日：2017-04-11
• [EN] 9-(ARYL OR HETEROARYL)-2-(PYRAZOLYL, PYRROLIDINYL OR CYCLOPENTYL)AMINOPURINE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DÉRIVÉS DE 9-(ARYL OU HÉTÉROARYL)-2-(PYRAZOLYL, PYRROLIDINYL OU CYCLOPENTYL)AMINOPURINE UTILISÉS EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：MERCK PATENT GMBH

  公开号：WO2014135245A1

  公开（公告）日：2014-09-12

  Compounds of the Formula (I) in which X, R1 and R2 have the meanings indicated in Claim 1, are inhibitors of GCN2, and can be employed, inter alia, for the treatment of cancer.
• Biochemical, cellular and structural characterization of novel and selective ERK3 inhibitors
  作者：Ulrich Grädler、Michael Busch、Birgitta Leuthner、Michael Raba、Lars Burgdorf、Martin Lehmann、Nina Linde、Christina Esdar

  DOI：10.1016/j.bmcl.2020.127551

  日期：2020.11

  Triazolo[4,5-d]pyrimidin-5-amines were identified from kinase selectivity screening as novel ERK3 inhibitors with sub-100 nanomolar potencies in a biochemical assay using MK5 as substrate and with an attractive kinase selectivity profile. ERK3 crystal structures clarified the inhibitor binding mode in the ATP pocket with impact on A-loop, GC-loop and αC-helix conformations suggesting a potential structural link towards MK5 interaction via the FHIEDE motif. The inhibitors also showed sub-100 nM potencies in a cellular ERK3 NanoBRET assay and with excellent correlation to the biochemical IC₅₀s. This novel series provides valuable tool compounds to further investigate the biological function and activation mechanism of ERK3.
• IMIDAZOPYRIMIDINE DERIVATIVES
  申请人：MERCK PATENT GMBH

  公开号：US20160002242A1

  公开（公告）日：2016-01-07

  Compounds of the formula I in which X, R 1 and R 2 have the meanings indicated in Claim 1, are inhibitors of GCN2, and can be employed, inter alia, for the treatment of cancer.

  公式I中的化合物，其中X，R1和R2具有声明1中指定的含义，是GCN2的抑制剂，可用于治疗癌症等方面。