5-(1-hydroxy-2,2-diphenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 1093117-07-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-hydroxy-2,2-diphenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1093117-07-7
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: GYUURIKNSFKZTB-UHFFFAOYSA-N

物化性质

• 熔点：
  49-51 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  572.1±50.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(1-hydroxy-2,2-diphenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 ethyl 2-methylene-4,4-diphenylbutanoate
  参考文献：
  名称：

  Optimization and Structure–Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides

  摘要：

  The oxytocinase subfamily of M1 aminopeptidases, Consisting of ER aminopeptidase 1 (ERAP1), ER aminopeptidase 2 (ERAP2), and insulin-regulated aminopeptidase (IRAP), plays critical roles in the generation of antigenic peptides and indirectly regulates human adaptive immune responses. We have previously,demonstrated that phosphinic pseudotripeptides can constitute potent inhibitors of this group of enzymes. In this study, we used synthetic methodologies able to furnish a series of stereochemically defined phosphinic pseudotripeptides and demonstrate that side chains at P-1' and P-2' positions are Critical determinants in driving potency and selectivity. We identified low nanomolar inhibitors of ERAP2 and IRAP that display selectivity of more than 2 and 3 orders of magnitude, respectively. Cellular analysis demonstrated that one of the compounds that is a selective IRAP inhibitor can reduce IRAP-dependent but not, ERAP1-dependent cross-presentation by dendritic cells with nanomolar efficacy. Our results encourage further preclinical development of phosphinic pseudotripeptides as regulators of adaptive immune responses.

  DOI：

  10.1021/acs.jmedchem.6b01031
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 二苯基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.58h， 以65%的产率得到5-(1-hydroxy-2,2-diphenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Efficient synthesis and biological evaluation of two modafinil analogues

  摘要：

  Non classical bioisosters of modafinil featuring interesting biological pro. le have been easily produced through replacement of the sulfoxide function with a carbonyl group and modification of the carboxylic acid amide functionality. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.027