APS-999 | 267223-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: APS-999
• 英文别名: (1R,2R,3aS,8bS)-5-(2-(1H-tetrazol-5-yl)ethyl)-1-((S,E)-4-cyclohexyl-3-hydroxybut-1-enyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-ol；(1R,2R,3aS,8bS)-1-[(E,3S)-4-cyclohexyl-3-hydroxybut-1-enyl]-5-[2-(2H-tetrazol-5-yl)ethyl]-2,3,3a,8b-tetrahydro-1H-cyclopenta[b][1]benzofuran-2-ol
• CAS: 267223-02-9
• 化学式: C₂₄H₃₂N₄O₃
• 分子量: 424.543
• InChiKey: VLFOPQQEYFUEHI-PQEHKDGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 吡啶 、 咪唑 、 sodium azide 、 草酰氯 、 四丁基氟化铵 、 氨 、 水 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 APS-999
  参考文献：
  名称：

  Efficient synthesis of a novel m-phenylene derivative as a selective EP4 agonist inducing follicular growth and maturation in the ovary

  摘要：

  An efficient and straightforward synthesis of a novel m-phenylene derivative has been developed. The optically pure dibromo compound was selected as a starting material. Through a protocol involving the Prins reaction and two steps of the Horner-Wadsworth-Emmons reaction, the basic skeleton was constructed with appropriate alpha and omega side chains. The compound proved to be a highly selective EP4 agonist and a possible drug candidate for maturation of the uterine cervix. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.004

文献信息

• Methods of neuroprotection involving Prostaglandin E2 EP4 (PGE2 EP4) receptor activation
  申请人：Andreasson Katrin

  公开号：US20120283293A1

  公开（公告）日：2012-11-08

  The present invention provides methods for attenuating neuronal inflammation and neuronal damage in case of acute or chronic injury of nerve cells of the central nervous system through prostaglandin E2 EP4 receptor activation. Methods for treating neuropathic pain are also provided.
• Efficient synthesis of a novel m-phenylene derivative as a selective EP4 agonist inducing follicular growth and maturation in the ovary
  作者：Ryoji Hayashi、Yutaka Hosono、Koji Nakatsuji、Yoichiro Tanaka、Takeshi Mori、Takami Kanno、Kei Makita、Mitsuhiro Moriwaki、Tomofumi Ohyama、Yasuo Ochi、Chifumi Inada、Masafumi Isogaya

  DOI：10.1016/j.bmcl.2011.09.004

  日期：2011.12

  An efficient and straightforward synthesis of a novel m-phenylene derivative has been developed. The optically pure dibromo compound was selected as a starting material. Through a protocol involving the Prins reaction and two steps of the Horner-Wadsworth-Emmons reaction, the basic skeleton was constructed with appropriate alpha and omega side chains. The compound proved to be a highly selective EP4 agonist and a possible drug candidate for maturation of the uterine cervix. (C) 2011 Elsevier Ltd. All rights reserved.