4-bromo-2,5-dimethoxy-β-nitrostyrene | 98537-45-2

• 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: 4-bromo-2,5-dimethoxy-β-nitrostyrene
• 英文别名: 1-Bromo-2,5-dimethoxy-4-(2-nitroethenyl)benzene
• CAS: 98537-45-2
• 化学式: C₁₀H₁₀BrNO₄
• 分子量: 288.098
• InChiKey: SYFSECIFVKQCOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2,5-dimethoxy-β-nitrostyrene 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 生成 4-溴-2,5二甲氧基苯乙胺
  参考文献：
  名称：

  WO2023/141469

  摘要：

  公开号：
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基苯 在 四氯化钛 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 4-bromo-2,5-dimethoxy-β-nitrostyrene
  参考文献：
  名称：

  5-HT_2A/5-HT_2C Receptor Pharmacology and Intrinsic Clearance of N-Benzylphenethylamines Modified at the Primary Site of Metabolism

  摘要：

  The toxic hallucinogen 25B-NBOMe is very rapidly degraded by human liver microsomes and has low oral bioavailability. Herein we report on the synthesis, microsomal stability, and S-HT2A/5-HT2C receptor profile of novel analogues of 25B-NBOMe modified at the primary site of metabolism. Although microsomal stability could be increased while maintaining potent 5-HT2 receptor agonist properties, all analogues had an intrinsic clearance above 1.3 L/kg/h predictive of high first-pass metabolism.

  DOI：

  10.1021/acschemneuro.6b00265

文献信息

• Ring-substituted β-methoxyphenethylamines: a new class of psychotomimetic agents active in man
  作者：D Lemaire、P Jacob、A T Shulgin

  DOI：10.1111/j.2042-7158.1985.tb03072.x

  日期：2011.4.12

  Four members of a new class of psychotomimetic agents have been synthesized and evaluated in man. These compounds, which incorporate a beta-methoxy group onto a beta-phenethylamine sidechain, are the first reported psychotomimetics which are structural analogues of the neurotransmitter noradrenaline. These substances are more potent than the corresponding phenethylamines (lacking a beta-methoxy group)

  一类新型拟精神病药物的四个成员已经合成并在人体中进行了评估。这些将β-甲氧基结合到β-苯乙胺侧链上的化合物是第一个报道的拟精神病药物，是神经递质去甲肾上腺素的结构类似物。这些物质比相应的苯乙胺（缺少β-甲氧基）更有效，但比相应取代的苯丙胺衍生物的效力更弱。
• Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity
  作者：Richard A. Glennon、Reva Raghupathi、Piotr Bartyzel、Milt Teitler、Sigrun Leonhardt

  DOI：10.1021/jm00082a014

  日期：1992.2

  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.