5-[3-chloro-4-(cyclohexyloxy)benzylidene]-1,3-thiazolidine-2,4-dione | 1239610-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[3-chloro-4-(cyclohexyloxy)benzylidene]-1,3-thiazolidine-2,4-dione
• 英文别名: 5-(3-chloro-4-(cyclohexyloxy)benzylidene)thiazolidine-2,4-dione；5-(3-Chloro-4-(cyclohexyloxy)benzylidene)thiazolidine-2,4-dione；5-[(3-chloro-4-cyclohexyloxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1239610-67-3
• 化学式: C₁₆H₁₆ClNO₃S
• 分子量: 337.827
• InChiKey: DKEZSRKQXRFEHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氯-4-羟基苯甲醛 、 环己醇 在 哌啶 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.0h， 生成 5-[3-chloro-4-(cyclohexyloxy)benzylidene]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Thiazolidinedione Analogues as 15-Hydroxyprostaglandin Dehydrogenase Inhibitors

  摘要：

  Novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitors were synthesized. Compounds 2, 3, and 4 exhibited IC(50) of 25, 8, and 19 nM, respectively. They also significantly increased levels of PGE(2) in A549 cells. To assess the influence of 15-PGDH inhibitor on cochlear blood flow (CBF), 2 was applied intravenously to guinea pigs. It increased their CBFs. Scratch wounds were also analyzed in confluent monolayers of HaCaT cells. Cells exposed to 4 showed significantly improved wound healing with respect to a control.

  DOI：

  10.1021/jm200390u

文献信息

• Synthesis and Biological Evaluation of Novel Thiazolidinedione Analogues as 15-Hydroxyprostaglandin Dehydrogenase Inhibitors
  作者：Ying Wu、Sandeep Karna、Cheol Hee Choi、Min Tong、Hsin-Hsiung Tai、Dong Hee Na、Chul Ho Jang、Hoon Cho

  DOI：10.1021/jm200390u

  日期：2011.7.28

  Novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase (15-PGDH) inhibitors were synthesized. Compounds 2, 3, and 4 exhibited IC(50) of 25, 8, and 19 nM, respectively. They also significantly increased levels of PGE(2) in A549 cells. To assess the influence of 15-PGDH inhibitor on cochlear blood flow (CBF), 2 was applied intravenously to guinea pigs. It increased their CBFs. Scratch wounds were also analyzed in confluent monolayers of HaCaT cells. Cells exposed to 4 showed significantly improved wound healing with respect to a control.