2-(2-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide | 934355-41-6

• 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: 2-(2-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
• 英文别名: 2-(bromophenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide；2-(2-bromophenyl)-N-(3-methoxyphenethyl)acetamide；2-(2-bromophenyl)-N-[2-(3-methoxyphenyl)ethyl]acetamide
• CAS: 934355-41-6
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: VGEVWTQLCUQNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 1-[(2-bromophenyl)methyl]-3,4-dihydro-6-methoxy-1H-isoquinoline-2-carboxaldehyde
  参考文献：
  名称：

  Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

  摘要：

  Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.038
• 作为产物：
  描述：

  邻溴苯乙酸 在 光气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide
  参考文献：
  名称：

  通过直接芳基化合成阿朴啡生物碱并使其多样化

  摘要：

  钯催化的芳基氯化物、溴化物和碘化物的直接芳基化已被应用于通过与苯并二恶唑、吡啶 N-氧化物和吡嗪 N-氧化物反应制备新的阿朴啡类似物，包括 C2 取代的阿朴啡。直接芳基化在这些多样化反应中的成功应用突出了其不仅在收敛合成中而且在发散合成中的效用。我们还描述了 (R)-nornuciferine 和 (R)-nuciferine 的对映选择性合成，采用催化不对称转移氢化以高产率和优异的对映体过量。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200600674

文献信息

• Identification of Novel 1-<i>O</i>-Substituted Aporphine Analogues as Potent 5-HT_2C Receptor Agonists
  作者：Qi Mao、Bingjie Zhang、Wanwan Li、Sheng Tian、Wenqing Shui、Na Ye

  DOI：10.1021/acschemneuro.9b00563

  日期：2020.2.19

  Our efforts to optimize our hit 15781 lead to the identification of the highly potent and selective 5-HT2C agonist 18b (MQ02-439) with an EC50 value of 104 nM and weak antagonism at the 5-HT2A and 5-HT2B receptors. The findings may serve as good starting points for the development of more potent and selective 5-HT2C agonists as valuable pharmacological tools or potential drug candidates.

  5-HT2C受体已成为治疗各种中枢神经系统疾病的有希望的靶标。我们首先确定了aphiphines是一种新型的5-HT2C受体激动剂。构效关系的结果表明，5-HT2C受体的活性可能需要阿啡肽核心，而其C1位置的取代对于5-HT2C受体的活性很重要。我们为优化热门产品15781而做出的努力导致鉴定出具有50 nM EC50值且对5-HT2A和5-HT2B受体具有弱拮抗作用的高效且选择性的5-HT2C激动剂18b（MQ02-439）。这些发现可以作为开发更有效和更具选择性的5-HT2C激动剂的宝贵起点，这些激动剂可以作为有价值的药理工具或潜在的候选药物。
• Structural optimizations and bioevaluation of N-H aporphine analogues as Gq-biased and selective serotonin 5-HT2C receptor agonists
  作者：Qi Mao、Bingjie Zhang、Sheng Tian、Wangzhi Qin、Jiaojiao Chen、Xi-Ping Huang、Ye Xin、Huicui Yang、Xue-Chu Zhen、Wenqing Shui、Na Ye

  DOI：10.1016/j.bioorg.2022.105795

  日期：2022.6
• Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells
  作者：Seikou Nakamura、Souichi Nakashima、Genzo Tanabe、Yoshimi Oda、Nami Yokota、Katsuyoshi Fujimoto、Takahiro Matsumoto、Rika Sakuma、Tomoe Ohta、Keiko Ogawa、Shino Nishida、Hisako Miki、Hisashi Matsuda、Osamu Muraoka、Masayuki Yoshikawa

  DOI：10.1016/j.bmc.2012.11.038

  日期：2013.2

  Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 2012 Elsevier Ltd. All rights reserved.
• Aporphine Alkaloid Synthesis and Diversification via Direct Arylation
  作者：Marc Lafrance、Nicole Blaquiere、Keith Fagnou

  DOI：10.1002/ejoc.200600674

  日期：2007.2

  aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric

  钯催化的芳基氯化物、溴化物和碘化物的直接芳基化已被应用于通过与苯并二恶唑、吡啶 N-氧化物和吡嗪 N-氧化物反应制备新的阿朴啡类似物，包括 C2 取代的阿朴啡。直接芳基化在这些多样化反应中的成功应用突出了其不仅在收敛合成中而且在发散合成中的效用。我们还描述了 (R)-nornuciferine 和 (R)-nuciferine 的对映选择性合成，采用催化不对称转移氢化以高产率和优异的对映体过量。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)