HU 250 | 119784-07-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: HU 250
• 英文别名: (2S,3S,4R,6S)-4,6-methanodibenzofuran-3'-ol-5'-(1'',1''-dimethylheptyl)-1,2,3,4,8,6-hexahydro-8,8-dimethyl-1-methylene；(1S,2S,10R,12S)-13,13-dimethyl-11-methylidene-6-(2-methyloctan-2-yl)-9-oxatetracyclo[10.1.1.02,10.03,8]tetradeca-3,5,7-trien-4-ol
• CAS: 119784-07-5
• 化学式: C₂₅H₃₆O₂
• 分子量: 368.56
• InChiKey: XDKSOXFRBATANJ-GPFNJZLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  HU 250 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以96%的产率得到(9bS)-1,3-methanodibenzofuran-9-ol-7-(1',1'-dimethylheptyl)-1,2,3,4,4a,9b-hexahydro-2,2-dimethyl-4-methyl
  参考文献：
  名称：

  WO2007/20631

  摘要：

  公开号：
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (1S,4S,5S)-4-[4-(1,1-dimethyl-heptyl)-2,6-dihydroxy-phenyl]-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 HU 250
  参考文献：
  名称：

  Cannabimimetic activity of novel enantiomeric, benzofuran cannabinoids

  摘要：

  The synthesis of the (2R,3R,4S,6R)-7/(2S,3S,4R,6S)-8 enantiomeric pair of benzofuran cannabinoids is reported together with the 1H and 13C NMR spectral parameters. In benzofuran 8 the configurational arrangement of ligated groups at the stereogenic C(3) atom (through which the terpene moiety is connected to the aromatic ring) is very similar to that of the corresponding atom in natural (3R,4R)-delta 1-tetrahydrocannabinol (delta 1-THC), although their respective Cahn-Ingold-Prelog descriptors are different. In drug-discrimination tests in pigeons and rats, benzofuran 8 is as active as delta 1-THC; in the mouse ring test compound 8 is more active than delta 6-THC. Enantiomer 7 is considerably less active than enantiomer 8 in both tests. These results can be explained by the fact that both 7 and 8 have a dimethylheptyl side chain (which is known to enhance cannabimimetic activity) and that delta 1-THC and benzofuran 8 have closely related conformations, as determined by molecular mechanics.

  DOI：

  10.1021/jm00165a024

文献信息

• MECHOULAM, RAPHAEL;BREUER, AVIVA;JARBE, TOBJORN U. C.;HILTUNEN, ARTO J.;G+, J. MED. CHEM., 33,(1990) N, C. 1037-1043
  作者：MECHOULAM, RAPHAEL、BREUER, AVIVA、JARBE, TOBJORN U. C.、HILTUNEN, ARTO J.、G+

  DOI：——

  日期：——
• WO2007/20631
  申请人：——

  公开号：——

  公开（公告）日：——
• Cannabimimetic activity of novel enantiomeric, benzofuran cannabinoids
  作者：Raphael Mechoulam、Aviva Breuer、Tobjorn U. C. Jaerbe、Arto J. Hiltunen、Robert Glaser

  DOI：10.1021/jm00165a024

  日期：1990.3

  The synthesis of the (2R,3R,4S,6R)-7/(2S,3S,4R,6S)-8 enantiomeric pair of benzofuran cannabinoids is reported together with the 1H and 13C NMR spectral parameters. In benzofuran 8 the configurational arrangement of ligated groups at the stereogenic C(3) atom (through which the terpene moiety is connected to the aromatic ring) is very similar to that of the corresponding atom in natural (3R,4R)-delta 1-tetrahydrocannabinol (delta 1-THC), although their respective Cahn-Ingold-Prelog descriptors are different. In drug-discrimination tests in pigeons and rats, benzofuran 8 is as active as delta 1-THC; in the mouse ring test compound 8 is more active than delta 6-THC. Enantiomer 7 is considerably less active than enantiomer 8 in both tests. These results can be explained by the fact that both 7 and 8 have a dimethylheptyl side chain (which is known to enhance cannabimimetic activity) and that delta 1-THC and benzofuran 8 have closely related conformations, as determined by molecular mechanics.