4-[3-[2-(4-Chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol | 1610430-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[3-[2-(4-Chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol
• 英文别名: 4-[3-[2-(4-chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol
• CAS: 1610430-62-0
• 化学式: C₁₉H₁₇ClN₂O₃
• 分子量: 356.809
• InChiKey: HFCMTGHLGFTCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(3-methoxymethoxypyridin-4-yl)-propionic acid ethyl ester 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 、 copper(I) bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 4-[3-[2-(4-Chlorophenoxy)pyridin-3-yl]oxypropyl]pyridin-3-ol
  参考文献：
  名称：

  Identification of 2,3-disubstituted pyridines as potent, non-emetic PDE4 inhibitors

  摘要：

  A series of 2,3-disubstituted pyridines were synthesized as potential non-emetic PDE4 inhibitors. To decrease brain exposure and minimize emesis, we modified the lipophilic moiety of a series of emetic PDE4 inhibitors and found that introduction of a hydroxy group into the pyridine moiety of the side chain led to non-emetic compounds with preserved PDE4 inhibitory activity. Following optimization at the phenoxy group, we identified compound 1 as a potent non-emetic PDE4 inhibitor. Compound 1 showed significant efficacy in an animal model of asthma without inducing emesis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.052

文献信息

• Identification of 2,3-disubstituted pyridines as potent, non-emetic PDE4 inhibitors
  作者：Motoji Kawasaki、Akira Fusano、Tomohiro Nigo、Shunya Nakamura、Mari N. Ito、Yasuhiro Teranishi、Satoshi Matsumoto、Hiroshi Toda、Naruaki Nomura、Takaaki Sumiyoshi

  DOI：10.1016/j.bmcl.2014.04.052

  日期：2014.6

  A series of 2,3-disubstituted pyridines were synthesized as potential non-emetic PDE4 inhibitors. To decrease brain exposure and minimize emesis, we modified the lipophilic moiety of a series of emetic PDE4 inhibitors and found that introduction of a hydroxy group into the pyridine moiety of the side chain led to non-emetic compounds with preserved PDE4 inhibitory activity. Following optimization at the phenoxy group, we identified compound 1 as a potent non-emetic PDE4 inhibitor. Compound 1 showed significant efficacy in an animal model of asthma without inducing emesis. (C) 2014 Elsevier Ltd. All rights reserved.