16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α | 64820-19-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α
• 英文别名: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-2-enoic acid
• CAS: 64820-19-5
• 化学式: C₂₃H₂₉F₃O₆
• 分子量: 458.475
• InChiKey: WWXGLANPEUCKKL-BPACVHNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2α-(6,6-dibromo-5-hexenyl)-3β-<4-<3-(trifluoromethyl)phenoxy>-3αβ-(tetrahydropyran-2-yloxy)-1-trans-butenyl>-4α-(tetrahydropyran-2-yloxy)cyclopentan-1-ol 在 Pd-BaSO₄ 吡啶 、 盐酸 、 正丁基锂 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-2,3-cis-didehydroprostaglandin F_1α
  参考文献：
  名称：

  Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain

  摘要：

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.

  DOI：

  10.1021/jm00179a011

文献信息

• Prostaglandin analogs possessing antinidatory effects. 2. Modification of the .alpha. chain
  作者：Masaki Hayashi、Yoshinobu Arai、Hirohisa Wakatsuka、Masanori Kawamura、Yoshitaka Konishi、Takeshi Tsuda、Kimiichiro Matsumoto

  DOI：10.1021/jm00179a011

  日期：1980.5

  Additional double bonds were introduced into the alpha chain in 16-phenoxy-, 16-(3-chlorophenoxy)-, 16-[3-(tri-fluoromethyl)phenoxy]-, and 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandins which have antinidatory effects. Of these analogues, the delta 3-cis-delta 5 analogues 23b is 1200 times more potent than prostaglandin F2 alpha in antinidatory effect in the rat and more potent than any other known prostaglandin analogues.