N-(3,4-dimethoxy-β-phenylethyl)octadecanamide | 858928-21-9

• 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: N-(3,4-dimethoxy-β-phenylethyl)octadecanamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]octadecanamide
• CAS: 858928-21-9
• 化学式: C₂₈H₄₉NO₃
• 分子量: 447.702
• InChiKey: LJMCOEUTELAQFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  32
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxy-β-phenylethyl)octadecanamide 在 sodium tetrahydroborate 、 五氯化磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-heptadecyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of a novel class of fatty acids-derived isoquinolines

  摘要：

  Two series of novel tetrahydroisoquinoline derivatives bearing at C-1 position a carbon chain derived from fatty acids were prepared employing two complementary synthetic methodologies. The Pictet-Spengler condensation was performed on myristyl, palmityl, stearyl and oleyl aldehydes, whereas the Bischler-Napieralski cyclization used pelargonic, stearic, linolenic and arachidonic acids. The ability to apply both methods allows further labeling of the final 1-substituted-1,2,3,4-tetrahydroisoquinolines for biological studies. (c) 2005 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2005.02.008
• 作为产物：
  描述：

  硬脂酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 N-(3,4-dimethoxy-β-phenylethyl)octadecanamide
  参考文献：
  名称：

  Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest

  摘要：

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.

  DOI：

  10.1021/ja042913p

文献信息

• Synthesis of 1-Alkyltetrahydroisoquinolines
  作者：A. Sh. Saidov、M. G. Levkovich、V. I. Vinogradova

  DOI：10.1007/s10600-013-0772-0

  日期：2013.11

  1-Alkyltetrahydroisoquinolines were prepared by a Bischler–Napieralski reaction starting from homoveratrylamine and monobasic acids. Their structures were confirmed by IR and NMR spectral data.

  1-烷基四氢异喹啉通过以同藜芦胺和一元羧酸为起始原料的Bischler-Napieralski反应制备。它们的结构通过红外和核磁共振光谱数据得以确认。
• Synthesis of a novel class of fatty acids-derived isoquinolines
  作者：Iwona Matuszewska、Andrzej Leniewski、Piotr Roszkowski、Zbigniew Czarnocki

  DOI：10.1016/j.chemphyslip.2005.02.008

  日期：2005.6

  Two series of novel tetrahydroisoquinoline derivatives bearing at C-1 position a carbon chain derived from fatty acids were prepared employing two complementary synthetic methodologies. The Pictet-Spengler condensation was performed on myristyl, palmityl, stearyl and oleyl aldehydes, whereas the Bischler-Napieralski cyclization used pelargonic, stearic, linolenic and arachidonic acids. The ability to apply both methods allows further labeling of the final 1-substituted-1,2,3,4-tetrahydroisoquinolines for biological studies. (c) 2005 Elsevier Ireland Ltd. All rights reserved.
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.