3-(4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)aniline | 1155810-59-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 3-(4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)aniline
• CAS: 1155810-59-5
• 化学式: C₁₆H₁₇N₅O
• 分子量: 295.344
• InChiKey: HFMDLESHJZWMPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三光气 、 3-(4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)aniline 、 N,N-二甲基乙二胺 在 三乙胺 作用下， 反应 2.0h， 生成 1-[2-(dimethylamino)ethyl]-3-[3-(4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)phenyl]urea
  参考文献：
  名称：

  PYRROLO[3,2-d]PYRIMIDINE COMPOUNDS AND THEIR USE AS PI3 KINASE AND mTOR KINASE INHIBITORS

  摘要：

  一种吡咯并[3,2-d]嘧啶化合物，例如具有以下式（I）的化合物：或其药用可接受的盐，其中构成变量如本文所定义，包括所述化合物的组合物，以及制备和使用所述化合物的方法。

  公开号：

  US20090149458A1
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 2.0h， 生成 3-(4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)aniline
  参考文献：
  名称：

  Synthesis and SAR of Novel 4-Morpholinopyrrolopyrimidine Derivatives as Potent Phosphatidylinositol 3-Kinase Inhibitors

  摘要：

  Significant evidence suggests that deregulation of the PI3K/Akt pathway is important in tumor progression. Mechanisms include loss of function of the tumor suppressor PTEN and high frequency of mutation of the PI3K p110 alpha isoform in human malignancies. This connection between PI3K and tumor genesis makes PI3K a promising target for cancer treatment. A series of 4-morpholinopyrrolopyrimidine derivatives were synthesized and evaluated as inhibitors of PI3K alpha and mTOR, leading to the discovery of PI3K alpha selective inhibitors (e.g., 9) and dual PI3K alpha/mTOR kinase inhibitors (e.g., 46 and 48). PI3K alpha/mTOR dual inhibitors demonstrated inhibition of tumor cell growth in vitro and in vivo and caused suppression of the pathway specific biomarkers [e.g., the phosphorylation of Akt at Thr308 (T308) and Ser473 (S473)] in the human breast cancer cell line MDA361. In addition, compound 46 demonstrated good in vivo efficacy in the MDA361 human breast tumor xenograft model.

  DOI：

  10.1021/jm901783v

文献信息

• SUBSTITUTED PENTA-FUSED HEXA-HETEROCYCLIC COMPOUNDS, PREPARATION METHOD THEREFOR, DRUG COMBINATION AND USE THEREOF
  申请人：Xiamen University

  公开号：US20200165246A1

  公开（公告）日：2020-05-28

  A type of substituted penta-fused hexa-heterocyclic compounds having selective inhibition for PIKfyve kinase, a pharmaceutically acceptable salt and pharmaceutically acceptable solvate thereof, a method for the preparation thereof, a pharmaceutical composition comprising the same, and use of these compounds in the manufacture of a medicament for preventing or treating a disease associated with PIKfyve in vivo, in particular in the manufacture of a medicament for preventing or treating tumor growth and metastasis.

  一种替代的五重融合六元杂环化合物，具有对PIKfyve激酶的选择性抑制作用，其药学上可接受的盐及其药学上可接受的溶剂，其制备方法，包括这些化合物的药物组合物，以及在制备用于预防或治疗与PIKfyve相关疾病的药物中使用这些化合物，特别是在制备用于预防或治疗肿瘤生长和转移的药物中。
• SUBSTITUTED PENTA- AND HEXA-HETEROCYCLIC COMPOUNDS, PREPARATION METHOD THEREFOR, DRUG COMBINATION AND USE THEREOF
  申请人：Xiamen University

  公开号：EP3663293A1

  公开（公告）日：2020-06-10

  A type of substituted penta- fused hexa-heterocyclic compounds having selective inhibition for PIKfyve kinase, a pharmaceutically acceptable salt and pharmaceutically acceptable solvate thereof, a method for the preparation thereof, a pharmaceutical composition comprising the same, and use of these compounds in the manufacture of a medicament for preventing or treating a disease associated with PIKfyve in vivo, in particular in the manufacture of a medicament for preventing or treating tumor growth and metastasis.

  一种对PIKfyve激酶具有选择性抑制作用的取代五融合六杂环化合物、其药学上可接受的盐和药学上可接受的溶液、其制备方法、包含这些化合物的药物组合物，以及这些化合物在制造预防或治疗体内PIKfyve相关疾病的药物中的用途，特别是在制造预防或治疗肿瘤生长和转移的药物中的用途。
• Substituted penta-fused hexa-heterocyclic compounds, preparation method therefor, drug combination and use thereof
  申请人：Xiamen University

  公开号：US11352354B2

  公开（公告）日：2022-06-07

  A type of substituted penta-fused hexa-heterocyclic compounds having selective inhibition for PIKfyve kinase, a pharmaceutically acceptable salt and pharmaceutically acceptable solvate thereof, a method for the preparation thereof, a pharmaceutical composition comprising the same, and use of these compounds in the manufacture of a medicament for preventing or treating a disease associated with PIKfyve in vivo, in particular in the manufacture of a medicament for preventing or treating tumor growth and metastasis.

  一种对PIKfyve激酶具有选择性抑制作用的取代五融合六六环化合物、其药学上可接受的盐和药学上可接受的溶液、其制备方法、包含这些化合物的药物组合物，以及这些化合物在制造预防或治疗体内PIKfyve相关疾病的药物中的用途，特别是在制造预防或治疗肿瘤生长和转移的药物中的用途。
• [EN] PYRROLO[3,2-D]PYRIMIDINE COMPOUNDS AND THEIR USE AS PI3 KINASE AND MTOR KINASE INHIBITORS<br/>[FR] COMPOSÉS DE PYRROLO[3,2-D]PYRIMIDINE ET LEUR UTILISATION COMME INHIBITEURS DE LA PI3 KINASE ET DE LA MTOR KINASE
  申请人：WYETH CORP

  公开号：WO2009070524A1

  公开（公告）日：2009-06-04

  A pyrrolo[3,2-d]pyrimidine compound, such as a compound of the formula (I); or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds, useful for treating PI3K-related diseases.