(E)-2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzylidene)ethanamine | 2177287-33-9

• 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: (E)-2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzylidene)ethanamine
• 英文别名: N-[2-(4-iodo-2,5-dimethoxyphenyl)ethyl]-1-(2-methoxyphenyl)methanimine
• CAS: 2177287-33-9；1798423-73-0
• 化学式: C₁₈H₂₀INO₃
• 分子量: 425.266
• InChiKey: XFKJLNFJWQOJQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  40
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzylidene)ethanamine 在 sodium tetrahydroborate 、 乙醇 作用下， 反应 2.0h， 以0.329 g的产率得到4-碘-2,5-二甲氧基-N-[(2-甲氧基苯基)甲基]苯乙胺
  参考文献：
  名称：

  25X-BOMes和25X-NBOHs（X = H，I，Br）的合成，用于药理研究和作为法医参考标准

  摘要：

  据报道，一种快速方法可合成三种NBOH（25H-，25I-和25B-NBOH；总产率为9–38％）和三种NBOM（25H-，25I-和25B-NBOMe；总产率为7–33％）。分别来自水杨醛和2-甲氧基醛。还确定了25H-，25I-和25B-NBOH.HCl的X射线结构。我们的方法应该为制备用于药理学和法医学目的的这类物质提供一个一般的入口。

  DOI：

  10.1016/j.tetlet.2020.152804
• 作为产物：
  描述：

  2,5-二甲氧基苯乙胺 在 碘 、 silver sulfate 作用下， 以 乙醇 为溶剂， 反应 48.5h， 生成 (E)-2-(4-iodo-2,5-dimethoxyphenyl)-N-(2-methoxybenzylidene)ethanamine
  参考文献：
  名称：

  25X-BOMes和25X-NBOHs（X = H，I，Br）的合成，用于药理研究和作为法医参考标准

  摘要：

  据报道，一种快速方法可合成三种NBOH（25H-，25I-和25B-NBOH；总产率为9–38％）和三种NBOM（25H-，25I-和25B-NBOMe；总产率为7–33％）。分别来自水杨醛和2-甲氧基醛。还确定了25H-，25I-和25B-NBOH.HCl的X射线结构。我们的方法应该为制备用于药理学和法医学目的的这类物质提供一个一般的入口。

  DOI：

  10.1016/j.tetlet.2020.152804

文献信息

• <i>N</i>-Benzyl-5-methoxytryptamines as Potent Serotonin 5-HT₂Receptor Family Agonists and Comparison with a Series of Phenethylamine Analogues
  作者：David E. Nichols、M. Flori Sassano、Adam L. Halberstadt、Landon M. Klein、Simon D. Brandt、Simon P. Elliott、Wolfgang J. Fiedler

  DOI：10.1021/cn500292d

  日期：2015.7.15

  A series of N-benzylated-5-methoxytryptarnine analogues was prepared and investigated, with special emphasis on substituents in the meta position of the benzyl group. A parallel series of several N-benzylated analogues of 2,5-dimethoxy-4-iodophenethylamine (2C-I) also was included for comparison of the two major templates (i.e., tryptamine and phenethylamine). A broad affinity screen at serotonin receptors showed that most of the compounds had the highest affinity at the 5-HT2 family receptors. Substitution at the para position of the benzyl group resulted in reduced affinity, whereas substitution in either the ortho or the meta position enhanced affinity. In general, introduction of a large lipophilic group improved affinity, whereas functional activity often followed the opposite trend. Tests of the compounds for functional activity utilized intracellular Ca2+ mobilization. Function was measured at the human 5-HT2A, 5-HT2B, and 5-HT2c receptors, as well as at the rat 5-HT2A and 5-HT2c receptors. There was no general correlation between affinity and function. Several of the tryptamine congeners were very potent functionally (EC50 values from 7.6 to 63 nM), but most were partial agonists. Tests in the mouse head twitch assay revealed that many of the compounds induced the head twitch and that there was a significant correlation between this behavior and functional potency at the rat 5-HT2A receptor.
• Synthesis and Structure–Activity Relationships of <i>N</i>-Benzyl Phenethylamines as 5-HT_2A/2C Agonists
  作者：Martin Hansen、Karina Phonekeo、James S. Paine、Sebastian Leth-Petersen、Mikael Begtrup、Hans Bräuner-Osborne、Jesper L. Kristensen

  DOI：10.1021/cn400216u

  日期：2014.3.19

  N-Benzyl substitution of 5-HT2A receptor agonists of the phenethylamine structural class of psychedelics (such as 4-bromo-2,5-dimethoxyphenethylamine, often referred to as 2C-B) confer a significant increase in binding affinity as well as functional activity of the receptor. We have prepared a series of 48 compounds with structural variations in both the phenethylamine and N-benzyl part of the molecule to determine the effects on receptor binding affinity and functional activity at 5-HT2A and 5-HT2c receptors. The compounds generally had high affinity for the 5-HT2A receptor with 8b having the highest affinity at 0.29 nM but with several other compounds also exhibiting subnanomolar binding affinities. The functional activity of the compounds was distributed over a wider range with lb being the most potent at 0.074 nM. Most of the compounds exhibited low to moderate selectivity (1- to 40-fold) for the 5-HT2A receptor in the binding assays, although one compound 6b showed an impressive 100-fold selectivity for the 5-HT2A receptor. In the functional assay, selectivity was generally higher with lb being more than 400-fold selective for the 5-HT2A receptor.
• Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes
  作者：Wellington Alves de Barros、Marcelo Pereira Queiroz、Leonardo da Silva Neto、Graziele Martins Borges、Felipe Terra Martins、Ângelo de Fátima

  DOI：10.1016/j.tetlet.2020.152804

  日期：2021.3

  reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes

  据报道，一种快速方法可合成三种NBOH（25H-，25I-和25B-NBOH；总产率为9–38％）和三种NBOM（25H-，25I-和25B-NBOMe；总产率为7–33％）。分别来自水杨醛和2-甲氧基醛。还确定了25H-，25I-和25B-NBOH.HCl的X射线结构。我们的方法应该为制备用于药理学和法医学目的的这类物质提供一个一般的入口。