3,4-Dimethyl-7-carbethoxyaminocoumarin | 92248-83-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,4-Dimethyl-7-carbethoxyaminocoumarin
• 英文别名: ethyl N-(3,4-dimethyl-2-oxochromen-7-yl)carbamate
• CAS: 92248-83-4
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: PQPWAVRAZAMXNL-UHFFFAOYSA-N

物化性质

• 熔点：
  199 °C(Solvent: Ethanol)
• 沸点：
  367.9±37.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-Dimethyl-7-carbethoxyaminocoumarin 在 硫酸 、 溶剂黄146 作用下， 生成 3,4-dimethyl-7-aminocoumarin
  参考文献：
  名称：

  新型香豆素氨基膦酸盐作为潜在的多靶点抗菌剂对抗金黄色葡萄球菌

  摘要：

  设计并合成了独特的香豆素氨基膦酸盐作为新型抗菌剂，以对抗严重的细菌耐药性。生物活性评估表明，具有低溶血活性的 3-羟基苯基氨基膦酸酯6f不仅在低浓度（0.5 μg/mL）体外对金黄色葡萄球菌表现出优异的抑制效力，而且在体内也表现出相当大的抗菌效力。同时，活性化合物6f能够根除金黄色葡萄球菌生物膜，从而减轻金黄色葡萄球菌耐药性的发展。此外，化合物6f的药物组合与诺氟沙星合用可增强抗菌效果。机理探索表明分子6f能够破坏细胞膜的完整性，导致蛋白质渗漏和代谢抑制。细胞氧化还原稳态通过诱导活性氧 (ROS) 和活性氮 (RNS) 的产生而受到干扰，导致谷胱甘肽 (GSH) 活性降低和脂质过氧化。此外，化合物6f可以嵌入 DNA 碱基对中，从而阻碍正常的生物学功能。上述结果为进一步开发香豆素氨基膦酸盐作为抗菌剂提供了有力的信息。

  DOI：

  10.1016/j.ejmech.2022.114891
• 作为产物：
  描述：

  3-氨基苯酚 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3,4-Dimethyl-7-carbethoxyaminocoumarin
  参考文献：
  名称：

  Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents

  摘要：

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.04.005

文献信息

• Methyltriazolocoumarins: New furocoumarin isosters as potential photochemotherapeutic agents
  作者：P. Rodighiero、A. Chilin、G. Pastorini、A. Guiotto、P. Manzini

  DOI：10.1002/jhet.5570270464

  日期：1990.5

  A number of new methyltriazolocoumarins with a linear psoralen-like structure or an angular angelicin-like structure were synthetized. The syntheses were performed starting from the appropriate methylated 7-aminocoumarins which were nitrated, reduced and successively diazotized with concomitant cyclization to form the condensed triazolo ring. The new methyltriazolocoumarins show promising spectroscopic

  合成了许多具有线性补骨脂素样结构或有角安吉辛样结构的新甲基三唑并香豆素。从合适的甲基化7-氨基香豆素开始进行合成，将其硝化，还原并随后伴随环化而重氮化以形成稠合的三唑环。新的甲基三唑并香豆素显示出有希望的光谱性质，这可能预示了它们的光化学和光生物学行为。
• RODIGHIERO, P.;CHILIN, A.;PASTORINI, G.;GUIOTTO, A.;MANZINI, P., J. HETEROCYCL. CHEM., 27,(1990) N, C. 1153-1158
  作者：RODIGHIERO, P.、CHILIN, A.、PASTORINI, G.、GUIOTTO, A.、MANZINI, P.

  DOI：——

  日期：——
• Design, synthesis, cytotoxicity and mechanism of novel dihydroartemisinin-coumarin hybrids as potential anti-cancer agents
  作者：Haonan Yu、Zhuang Hou、Ye Tian、Yanhua Mou、Chun Guo

  DOI：10.1016/j.ejmech.2018.04.005

  日期：2018.5

  To develop novel agents with anticancer activities, thirty-four new dihydroartemisinin-coumarin hybrids were designed and synthesized in this study. Those compounds were identified that had great anticancer activity against two cancer cell lines (MDA-MB-231 and HT-29). The structure-activity relationships of the derivatives were also discussed, and the results of docking analysis had shown that carbonic anhydrases IX (CA IX) was very likely to be one of the drug targets of the hybrids. Meanwhile, to clarify the mechanism of the anticancer activity of the hybrids molecule, we did further exploration in the bioactivity of the hybrids. The results had shown that these derivatives obviously inhibited proliferation of HT-29 cell lines, arrested G(0)/G(1) phase of HT-29 cells, suppressed the migration of tumor cells, and induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells. Interestingly, the hybrids also induced the other cell death pathway-ferroptosis. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Novel coumarin aminophosphonates as potential multitargeting antibacterial agents against Staphylococcus aureus
  作者：Xun-Cai Yang、Chun-Mei Zeng、Srinivasa Rao Avula、Xin-Mei Peng、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2022.114891

  日期：2023.1

  aminophosphonates as new antibacterial agents were designed and synthesized to combat severely bacterial resistance. Bioactivity assessment identified that 3-hydroxylphenyl aminophosphonate 6f with low hemolytic activity not only exhibited excellent inhibition potency against Staphylococcus aureus at low concentration (0.5 μg/mL) in vitro but also showed considerable antibacterial potency in vivo. Meanwhile

  设计并合成了独特的香豆素氨基膦酸盐作为新型抗菌剂，以对抗严重的细菌耐药性。生物活性评估表明，具有低溶血活性的 3-羟基苯基氨基膦酸酯6f不仅在低浓度（0.5 μg/mL）体外对金黄色葡萄球菌表现出优异的抑制效力，而且在体内也表现出相当大的抗菌效力。同时，活性化合物6f能够根除金黄色葡萄球菌生物膜，从而减轻金黄色葡萄球菌耐药性的发展。此外，化合物6f的药物组合与诺氟沙星合用可增强抗菌效果。机理探索表明分子6f能够破坏细胞膜的完整性，导致蛋白质渗漏和代谢抑制。细胞氧化还原稳态通过诱导活性氧 (ROS) 和活性氮 (RNS) 的产生而受到干扰，导致谷胱甘肽 (GSH) 活性降低和脂质过氧化。此外，化合物6f可以嵌入 DNA 碱基对中，从而阻碍正常的生物学功能。上述结果为进一步开发香豆素氨基膦酸盐作为抗菌剂提供了有力的信息。