3-(4-ethoxyphenyl)-N-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]triazolo[4,5-d]pyrimidin-5-amine | 1448693-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-ethoxyphenyl)-N-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]triazolo[4,5-d]pyrimidin-5-amine
• 英文别名: [3-(4-ethoxyphenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl][1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]amine；3-(4-ethoxyphenyl)-N-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)-3H-[1,2,3]triazolo [4,5-d]pyrimidin-5-amine；3-(4-ethoxyphenyl)-N-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]triazolo[4,5-d]pyrimidin-5-amine
• CAS: 1448693-04-6
• 化学式: C₂₁H₂₅N₉O
• 分子量: 419.489
• InChiKey: GYJNFCRUTKYKNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  对乙氧基苯胺 在 盐酸 、 氢气 、 镍 、 三乙胺 、 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

文献信息

• [EN] TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZOLO[4,5-D]PYRIMIDINE
  申请人：MERCK PATENT GMBH

  公开号：WO2013110309A1

  公开（公告）日：2013-08-01

  Compounds of the formula (I) in which 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.

  式（I）中R1和R2具有索引中指示的含义的化合物是GCN2的抑制剂，可用于治疗癌症。
• TRIAZOLO[4,5-D]PYRIMIDINE DERIVATIVES
  申请人：Merck Patent GmbH

  公开号：US20140378431A1

  公开（公告）日：2014-12-25

  Compounds of the formula I in which 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，其中R1和R2的含义如权利要求1所示的化合物是GCN2的抑制剂，可用于治疗癌症等疾病。
• Triazolo[4,5-d]pyrimidin-5-amines based ERK3 inhibitors fail to demonstrate selective effects on adipocyte function
  作者：Andrei Belykh、Izabela Hawro、Katarzyna Kolczyńska-Matysiak、Angel Loza-Valdes、Adam Mieczkowski、Grzegorz Sumara

  DOI：10.1016/j.abb.2023.109825

  日期：2024.1
• US9409914B2
  申请人：——

  公开号：US9409914B2

  公开（公告）日：2016-08-09
• [EN] HETEROCYCLIC GCN2 MODULATORS<br/>[FR] MODULATEURS DE GCN2 HÉTÉROCYCLIQUES
  申请人：HIBERCELL INC

  公开号：WO2021222147A1

  公开（公告）日：2021-11-04

  The invention relates to methods of using modulators of GCN2 and compositions thereof, in the treatment of cancers and other diseases and disorders associated with GCN2 activation, said modulators having the Formulae I, II, III, IV, V, VI, VII, and/or VIII.