8-(5-amino-1H-[1,2,4]triazol-3-ylsulfanylmethyl)-3-butyl-7-ethyl-3,7-dihydro-purine-2,6-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-(5-amino-1H-[1,2,4]triazol-3-ylsulfanylmethyl)-3-butyl-7-ethyl-3,7-dihydro-purine-2,6-dione
• 英文别名: 8-(5-amino-1H-[1,2,4]triazol-3-ylsulfanylmethyl)-3-butyl-7-ethyl-3,7-dihydropurine-2,6-dione；8-[(5-amino-1H-1,2,4-triazol-3-yl)sulfanylmethyl]-3-butyl-7-ethylpurine-2,6-dione
• 化学式: C₁₄H₂₀N₈O₂S
• 分子量: 364.431
• InChiKey: MXIGEXYNJXBRRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  160
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-butyl-N'-cyanoacetylurea 在 盐酸 、 氯化亚砜 、 sodium dithionite 、 氨 、 potassium carbonate 、 N,N-二异丙基乙胺 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 乙醇-D1 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 8-(5-amino-1H-[1,2,4]triazol-3-ylsulfanylmethyl)-3-butyl-7-ethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins

  摘要：

  A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.

  DOI：

  10.1021/acs.jmedchem.5b01708

文献信息

• [EN] XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS<br/>[FR] DÉRIVÉS DE XANTHINE INHIBITEURS DE PROTÉINES BET
  申请人：INSERM (INSTITUT NAT DE LA SANTÉ ET DE LA RECH MÉDICALE)

  公开号：WO2017114843A1

  公开（公告）日：2017-07-06

  This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

  本发明涉及一种抑制BET溴结构域蛋白的黄嘌呤衍生物化合物，以及其制备方法和应用。
• Xanthine derivative inhibitors of BET proteins
  申请人：Centre national de la recherche scientifique

  公开号：US11225481B2

  公开（公告）日：2022-01-18

  This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

  本发明涉及作为 BET 溴链蛋白抑制剂的黄嘌呤衍生物化合物、其制备方法及其应用。
• XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS
  申请人：INSERM - Institut National de la Santé et de la Recherche Médicale

  公开号：EP3397640A1

  公开（公告）日：2018-11-07
• Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins
  作者：Brigitt Raux、Yuliia Voitovich、Carine Derviaux、Adrien Lugari、Etienne Rebuffet、Sabine Milhas、Stéphane Priet、Thomas Roux、Eric Trinquet、Jean-Claude Guillemot、Stefan Knapp、Jean-Michel Brunel、Alexey Yu. Fedorov、Yves Collette、Philippe Roche、Stéphane Betzi、Sébastien Combes、Xavier Morelli

  DOI：10.1021/acs.jmedchem.5b01708

  日期：2016.2.25

  A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.