3-chloro-4-(3-cyclohexylpropoxy)benzaldehyde | 1234323-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-4-(3-cyclohexylpropoxy)benzaldehyde
• 英文别名: 3-Chloro-4-(3-cyclohexylpropoxy)benzaldehyde
• CAS: 1234323-07-9
• 化学式: C₁₆H₂₁ClO₂
• 分子量: 280.795
• InChiKey: ZWIRRTBSFOAKKL-UHFFFAOYSA-N

物化性质

• 沸点：
  403.1±25.0 °C(predicted)
• 密度：
  1.111±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 3-chloro-4-(3-cyclohexylpropoxy)benzaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以88%的产率得到5-[3-chloro-4-(3-cyclohexylpropoxy)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
• 作为产物：
  描述：

  3-环已基-1-丙醇 、 3-氯-4-羟基苯甲醛 在 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 18.0h， 生成 3-chloro-4-(3-cyclohexylpropoxy)benzaldehyde
  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

• NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
  申请人：Cho Hoon

  公开号：US20110269954A1

  公开（公告）日：2011-11-03

  The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

  本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物及其用途。更具体地说，本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物以及包含其的药物组合物。根据本发明的式（I）的新型噻唑烷二酮衍生物可以通过抑制分解前列腺素的15-羟基前列腺素脱氢酶（15-PGDH）的活性，有效用于预防或治疗心血管疾病、胃肠道疾病和肾脏疾病，同时也用于预防脱发和促进头发生长，以及促进骨生成和伤口愈合。
• US8637558B2
  申请人：——

  公开号：US8637558B2

  公开（公告）日：2014-01-28
• 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.