4-Bromo-2-methoxy-1-(2-nitroprop-1-enyl)benzene | 99641-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-Bromo-2-methoxy-1-(2-nitroprop-1-enyl)benzene
• CAS: 99641-62-0
• 化学式: C₁₀H₁₀BrNO₃
• 分子量: 272.098
• InChiKey: SOKSWFOCVURSLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Bromo-2-methoxy-1-(2-nitroprop-1-enyl)benzene 在 aluminium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以61%的产率得到1-(2-methoxy-4-bromophenyl)-2-aminopropane
  参考文献：
  名称：

  5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogs

  摘要：

  1-(2,5-Dimethoxy-4-bromophenyl)-2-aminopropane (DOB; 1a) is a purported serotonin (5-HT) agonist that binds selectively to central 5-HT2 binding sites. Systematic removal of any or all of the aromatic substituents had relatively little effect on 5-HT1 binding but reduced 5-HT2 binding by approximately 2 or more orders of magnitude. Demethylation of the 2-methoxy group of 1a, or introduction of an N-n-propyl group, doubled 5-HT1-site affinity but decreased 5-HT2-site affinity by 3- and 30-fold, respectively. In tests of stimulus generalization, using rats trained to discriminate DOM from saline, the 2-demethyl and N-propyl derivatives were found to produce stimulus effects similar to those of DOB. In addition, the S-(+) isomer of the iodo analogue of 1a was found to possess one-third the affinity of its R-(-) enantiomer at 5-HT2 sites and also resulted in DOM-stimulus generalization. Of the DOB analogues examined, DOB (1a) possesses optimal selectivity for 5-HT2 binding.

  DOI：

  10.1021/jm00152a005
• 作为产物：
  描述：

  4-溴-2-羟基苯甲醛 在 乙酸铵 、 aluminum oxide 、 potassium fluoride 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 68.0h， 生成 4-Bromo-2-methoxy-1-(2-nitroprop-1-enyl)benzene
  参考文献：
  名称：

  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity

  摘要：

  Certain phenylalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors. It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors. The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other. An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = > 0.9, n = 25) between 5-HT1C and 5-HT2 affinity. None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.

  DOI：

  10.1021/jm00082a014

文献信息

• Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists
  作者：Emil Marcher-Rørsted、Adam L. Halberstadt、Adam K. Klein、Muhammad Chatha、Simon Jademyr、Anders A. Jensen、Jesper L. Kristensen

  DOI：10.1021/acschemneuro.0c00129

  日期：2020.5.6

  agonist activity at the serotonin 2A receptor (5-HT2AR). The 2,5-dimethoxy motif is present in several classical phenethylamine psychedelics such as 2,4,5- trimethoxyamphetamine (TMA-2), 2,5-dimethoxy-4-methylamphetamine (DOM), 2,5-dimethoxy-4-iodoamphetamine (DOI), 2,5- dimethoxy-4-bromoamphetamine (DOB), 2,5-dimethoxy-4-bromophenethylamine (2C-B), and 2,5-dimethoxy-4-iodophenethylamine (2C-I), and it has

  2,5-二甲氧基苯乙胺（2,5-PEA）支架被认为是赋予5-羟色胺2A受体（5-HT2AR）潜在激动剂活性的基序。2,5-二甲氧基基序存在于几种经典的苯乙胺迷幻药中，例如2,4,5-三甲氧基苯丙胺（TMA-2），2,5-二甲氧基-4-甲基苯丙胺（DOM），2,5-二甲氧基-4-碘苯丙胺（DOI），2,5-二甲氧基-4-溴苯丙胺（DOB），2,5-二甲氧基-4-溴苯乙胺（2C-B）和2,5-二甲氧基-4-碘苯乙胺（2C-1）和先前已经提出，该结构基序对于5-HT 2AR活化是必不可少的。在本研究中，我们提出了挑战这一假设的数据。合成了2C-B和DOB的2-和5-去甲氧基衍生物 通过在结合和功能测定中在5-HT2AR和5-HT2CR的体外评估其药理学特征，并通过评估它们对小鼠头抽搐反应的诱导来评估其药理学特征。消除2-或5-甲氧基基团导致在5-HT 2AR和5-HT 2CR的结合亲和力和功能效