3-(4-nitrobenzyl)-5-[(Z)-1-phenylmethylidene]-1,3-thiazolane-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-nitrobenzyl)-5-[(Z)-1-phenylmethylidene]-1,3-thiazolane-2,4-dione
• 英文别名: 3-(4-nitrobenzyl)-5-[(Z)-phenylmethylidene]-1,3-thiazolidine-2,4-dione；(5Z)-5-benzylidene-3-[(4-nitrophenyl)methyl]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₇H₁₂N₂O₄S
• 分子量: 340.359
• InChiKey: UABQQUDUUUKMGB-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (Z)-5-benzylidene-1,3-thiazolidine-2,4-dione 、 对硝基溴化苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以78%的产率得到3-(4-nitrobenzyl)-5-[(Z)-1-phenylmethylidene]-1,3-thiazolane-2,4-dione
  参考文献：
  名称：

  Discovery and Optimization of Boronic Acid Based Inhibitors of Autotaxin

  摘要：

  Autotaxin (ATX) is an extracellular enzyme that hydrolyzes lysophosphatidylcholine (LPC) to produce the lipid mediator lysophosphatidic acid (LPA). The ATX LPA signaling axis has been implicated in diverse physiological and pathological processes, including vascular development, inflammation, fibrotic disease, and tumor progression. Therefore targeting ATX with small molecule inhibitors is an attractive therapeutic strategy. We recently reported that 2,4-thiazolidinediones inhibit ATX activity in the micromolar range. Interestingly, inhibitory potency was dramatically increased by introduction of a boronic acid moiety, designed to target the active site threonine in ATX. Here we report on the discovery and further optimization of boronic acid based ATX inhibitors. The most potent of these compounds inhibits ATX-mediated LPC hydrolysis in the nanomolar range (IC50 = 6 nM). The finding that ATX can be targeted by boronic acids may aid the development of ATX inhibitors for therapeutic use.

  DOI：

  10.1021/jm1005012

文献信息

• Organic Reactions in Ionic Liquids;Ionic Liquid-Accelerated Three-Component Reaction: A Rapid One-PotSynthesis of 3-Alkyl-5-[(<i>Z</i>)-arylmethylidene]-1,3-thiazolidine-2,4-diones
  作者：Zhen-Chu Chen、De-Hong Yang、Song-Ying Chen、Qin-Guo Zheng

  DOI：10.1055/s-2003-40980

  日期：——

  A rapid one-pot synthesis of 3-alkyl-5-[(Z)-arylme­thylidene]-1,3-thiazolidine-2,4-dionesis described that occurs in recyclable ionic liquid [bmim]PF6 (1-butyl-3-methylimidazolium hexafluorophosphate).Significant rate enhancement and good selectivity have been observed.

  描述了在可回收离子液体 [bmim]PF6 （1-丁基-3-甲基咪唑鎓六氟磷酸盐）中快速单锅合成 3-烷基-5-[(Z)-芳基亚甲基]-1,3-噻唑烷-2,4-二酮的过程。