1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)propane | 111381-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)propane
• 英文别名: 2,2,2-trifluoro-N-[1-(4-iodo-2,5-dimethoxyphenyl)propan-2-yl]acetamide
• CAS: 111381-04-5
• 化学式: C₁₃H₁₅F₃INO₃
• 分子量: 417.167
• InChiKey: QVWLZXDQSXYTFI-UHFFFAOYSA-N

物化性质

• 沸点：
  436.6±45.0 °C(Predicted)
• 密度：
  1.576±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)propane 在 sodium hydroxide 作用下， 反应 14.0h， 以65%的产率得到4-(2-氯乙基)-1,2-二甲氧基苯
  参考文献：
  名称：

  [125I] -1-（2,5-二甲氧基-4-碘苯基）-2-氨基丙烷：一种碘标记的放射性配体，专门标记了5-HT2 5-羟色胺受体的激动剂高亲和力状态。

  摘要：

  DOI：

  10.1021/jm00396a003
• 作为产物：
  描述：

  2-氨基-4-苯基丙烷盐酸盐 生成 1-(2,5-dimethoxy-4-iodophenyl)-2-(trifluoroacetamido)propane
  参考文献：
  名称：

  [125I] -1-（2,5-二甲氧基-4-碘苯基）-2-氨基丙烷：一种碘标记的放射性配体，专门标记了5-HT2 5-羟色胺受体的激动剂高亲和力状态。

  摘要：

  DOI：

  10.1021/jm00396a003

文献信息

• 1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: A Potent Serotonin 5-HT2A/2C Agonist
  作者：David E. Nichols、Stewart Frescas、Danuta Marona-Lewicka、Xuemei Huang、Bryan L. Roth、Gary A. Gudelsky、J. Frank Nash

  DOI：10.1021/jm00051a011

  日期：1994.12

  A method was found to synthesize 1-(2,5-dimethoxy-4-(trifluoromethyl) phenyl)-2-aminopropane, 5, and its des-alpha-methyl congener 2-(2,5-dimethoxy-4-(trifluoromethyl)phenyl)aminoethane, 6, the trifluoromethyl analogs of substituted hallucinogenic phenethylamine derivatives such as 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (3, DOI) that are potent 5-HT2A/2C agonists. In our hands, 5 and 6 have

  发现一种合成1-（2,5-二甲氧基-4-（三氟甲基）苯基）-2-氨基丙烷5及其脱α-甲基同源物2-（2,5-二甲氧基-4-（三氟甲基）的方法）苯基）氨基乙烷，6，取代的致幻剂苯乙胺衍生物的三氟甲基类似物，例如1-（2,5-二甲氧基-4-碘苯基）-2-氨基丙烷（3，DOI），它们是有效的5-HT2A / 2C激动剂。在我们手中，已证明5和6对大鼠皮质中的[3H]酮色林或[125I] -3-标记的5-HT2A / 2C位点具有亲和力，其亲和力高于或高于类似的溴或碘类似物。类似地，在训练用于从酒石酸LSD区分盐水的大鼠的两杆药物歧视试验中，5和6的效价与它们的溴或碘同类物相当或稍高。通过测量[3H]肌醇单磷酸酯在选择性表达5-HT2A或5-HT2C受体的培养细胞中的积累来评估5和6的激动剂性质。与5-羟色胺（5-HT）相比，化合物3（DOI），5和6对5-HT2C受体具有同等效力和完全激动剂。类似地，与5-HT相比，3和5在5-HT
• 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT_2A Partial Agonists
  作者：Cynthia S. Dowd、Katharine Herrick-Davis、Christina Egan、Ann DuPre、Carol Smith、Milt Teitler、Richard A. Glennon

  DOI：10.1021/jm9906062

  日期：2000.8.1

  Phenylalkylamines such as 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane (DOB; Pa) and its corresponding iodo derivative DOI (2) are commonly used 5-HT2 serotonin agonists. Previous studies have established that the 2,5-dimethoxy substitution pattern found in these compounds is optimal for high affinity at 5-HT2A receptors and that substituents at the 4-position can modulate affinity over a wide range. We have previously shown, however, that when the 4-position is substituted with a 3-phenylpropyl substituent (i.e., 3), the compound binds with an affinity comparable to that of Pa but that it possesses 5-HT2A antagonist character. The present study examined the structure-affinity relationships of 3, and the results were very much unexpected. That is, the 2,5-dimethoxy substitution pattern of 3 is not required for high affinity. Either of the two methoxy groups can be removed without untoward effect on affinity, and relocation of the methoxy substituents actually enhances affinity by as much as an order of magnitude. None of the compounds displayed more than 20-fold selectivity for 5-HT2A over 5-HT2C receptors. In addition, several were demonstrated to act as 5-HT2A partial agonists. As such, the results of this study suggest that the structure-affinity relationships of phenylalkylamines as 5-HT2A ligands now be reinvestigated in greater detail.
• Synthesis of 2,3-dimethoxy-5-iodobenzoic acid
  作者：Eddy W. Yue、John M. Gerdes、Chester A. Mathis

  DOI：10.1021/jo00018a048

  日期：1991.8
• Nichols David E., Frescas Stewart, Marona-Lewicka Danuta, Huang Xuemei, R+, J. Med. Chem, 37 (1994) N 25, S 4346-4351
  作者：Nichols David E., Frescas Stewart, Marona-Lewicka Danuta, Huang Xuemei, R+

  DOI：——

  日期：——