KM-233-m-bromo | 1046146-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: KM-233-m-bromo
• 英文别名: 3-[1-(3-Bromo-phenyl)-1-methyl-ethyl]-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol；(6aR,10aR)-3-[2-(3-bromophenyl)propan-2-yl]-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 1046146-01-3
• 化学式: C₂₅H₂₉BrO₂
• 分子量: 441.408
• InChiKey: HJVPRKXONIWSBC-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(1-(3-bromo-phenyl)-1-methyl-ethyl)-benzene-1,3-diol 、 (+)-Δ²-p-menthene-1,8-diol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以21.3%的产率得到KM-233-m-bromo
  参考文献：
  名称：

  Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

  摘要：

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.034

文献信息

• Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs
  作者：Mathangi Krishnamurthy、Steven Gurley、Bob M. Moore II

  DOI：10.1016/j.bmc.2008.05.034

  日期：2008.7.1

  The synthesis and characterization of novel C1'-phenyl-substituted Delta(8)-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1'-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a K-i 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2. (c) 2008 Elsevier Ltd. All rights reserved.