[2-氧代-4-(三氟甲基)-2H-1-苯并吡喃-7-基]氨基甲酸乙酯 | 63450-46-4

• 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
• 中文名称: [2-氧代-4-(三氟甲基)-2H-1-苯并吡喃-7-基]氨基甲酸乙酯
• 英文名称: 7-(Carbethoxyamido)-4-(trifluoromethylcoumarin)
• 英文别名: 7-(carbethoxyamino)-4-(trifluoromethyl)coumarin；ethyl [2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]carbamate；Carbamic acid, [2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-, ethyl ester；ethyl N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamate
• CAS: 63450-46-4
• 化学式: C₁₃H₁₀F₃NO₄
• 分子量: 301.222
• InChiKey: VUJLMASTRUYUHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  [2-氧代-4-(三氟甲基)-2H-1-苯并吡喃-7-基]氨基甲酸乙酯 在 硫酸 、 溶剂黄146 作用下， 生成 香豆素 151
  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 [2-氧代-4-(三氟甲基)-2H-1-苯并吡喃-7-基]氨基甲酸乙酯
  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

• Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function
  作者：Abha Kathuria、Nivedita Priya、Karam Chand、Prabhjot Singh、Anjali Gupta、Sarah Jalal、Shilpi Gupta、Hanumantharao G. Raj、Sunil K. Sharma

  DOI：10.1016/j.bmc.2011.11.016

  日期：2012.2

  Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and chemistry of 7-amino-4-(trifluoromethyl)coumarin and its amino acid and peptide derivatives
  作者：Eugene R. Bissell、Alexander R. Mitchell、Robert E. Smith

  DOI：10.1021/jo01300a003

  日期：1980.6