(Z)-5-(4-(3-(piperidin-1-yl)propoxy)benzylidene)thiazolidine-2,4-dione | 1222824-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-(4-(3-(piperidin-1-yl)propoxy)benzylidene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[4-(3-piperidin-1-ylpropoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1222824-14-7
• 化学式: C₁₈H₂₂N₂O₃S
• 分子量: 346.45
• InChiKey: LZUCPOFPEFITOA-SSZFMOIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-(4-(3-(piperidin-1-yl)propoxy)benzylidene)thiazolidine-2,4-dione 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、500.01 kPa 条件下， 反应 48.0h， 以67%的产率得到5-(4-(3-(piperidin-1-yl)propoxy)benzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Acidic elements in histamine H3 receptor antagonists

  摘要：

  Antagonists of the human histamine H-3 receptor (hH(3)R) often contain a second basic moiety, which is well known to boost affinity on this histamine receptor subtype. Here, we prepared compounds with acidic moieties of different pK(a) values to figure out that the hH(3)R tolerates these functionalities when added to a common pharmacophore blueprint. Depending on the acidic, electronic and steric features the designed ligands showed hH(3)R affinities in the nanomolar concentration range. Additionally, selected ligands were tested but failed as dual acting hH(3)R/hPPAR (human peroxisome proliferator-activated receptor) ligands. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.089
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 4-(3-(piperidin-1-yl)propoxy)benzaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以46%的产率得到(Z)-5-(4-(3-(piperidin-1-yl)propoxy)benzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Acidic elements in histamine H3 receptor antagonists

  摘要：

  Antagonists of the human histamine H-3 receptor (hH(3)R) often contain a second basic moiety, which is well known to boost affinity on this histamine receptor subtype. Here, we prepared compounds with acidic moieties of different pK(a) values to figure out that the hH(3)R tolerates these functionalities when added to a common pharmacophore blueprint. Depending on the acidic, electronic and steric features the designed ligands showed hH(3)R affinities in the nanomolar concentration range. Additionally, selected ligands were tested but failed as dual acting hH(3)R/hPPAR (human peroxisome proliferator-activated receptor) ligands. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.089

文献信息

• Acidic elements in histamine H3 receptor antagonists
  作者：Kerstin Sander、Yvonne von Coburg、Jean-Claude Camelin、Xavier Ligneau、Oliver Rau、Manfred Schubert-Zsilavecz、Jean-Charles Schwartz、Holger Stark

  DOI：10.1016/j.bmcl.2010.01.089

  日期：2010.3

  Antagonists of the human histamine H-3 receptor (hH(3)R) often contain a second basic moiety, which is well known to boost affinity on this histamine receptor subtype. Here, we prepared compounds with acidic moieties of different pK(a) values to figure out that the hH(3)R tolerates these functionalities when added to a common pharmacophore blueprint. Depending on the acidic, electronic and steric features the designed ligands showed hH(3)R affinities in the nanomolar concentration range. Additionally, selected ligands were tested but failed as dual acting hH(3)R/hPPAR (human peroxisome proliferator-activated receptor) ligands. (C) 2010 Elsevier Ltd. All rights reserved.