2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxylic acid | 1286678-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxylic acid
• CAS: 1286678-93-0
• 化学式: C₂₁H₂₀N₄O₄S
• 分子量: 424.48
• InChiKey: XFJVKUJZZUNPGQ-HDICACEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-(1-isobutoxyethyl)hydroxylamine 、 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以0.255 g的产率得到
  参考文献：
  名称：

  Design and synthesis of novel pyrimidine hydroxamic acid inhibitors of histone deacetylases

  摘要：

  Inhibition of histone deacetylase activity represents a promising new modality in the treatment of a number of cancers. A novel HDAC series demonstrating inhibitory activity in cell proliferation assays is described. Optimisation based on the introduction of basic amine linkers to effect good drug distribution to tumour led to the identification of a compound with oral activity in a human colon cancer xenograft study associated with increased histone H3 acetylation in tumour tissue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.016
• 作为产物：
  描述：

  ethyl 2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到2-[5-(naphthalene-2-sulfonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]-pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of novel pyrimidine hydroxamic acid inhibitors of histone deacetylases

  摘要：

  Inhibition of histone deacetylase activity represents a promising new modality in the treatment of a number of cancers. A novel HDAC series demonstrating inhibitory activity in cell proliferation assays is described. Optimisation based on the introduction of basic amine linkers to effect good drug distribution to tumour led to the identification of a compound with oral activity in a human colon cancer xenograft study associated with increased histone H3 acetylation in tumour tissue. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.016