6-acetyl-3-ethyl-7-hydroxy-4-methyl-2H-chromen-2-one

• 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: 6-acetyl-3-ethyl-7-hydroxy-4-methyl-2H-chromen-2-one
• 英文别名: 6-Acetyl-3-ethyl-7-hydroxy-4-methylchromen-2-one；6-acetyl-3-ethyl-7-hydroxy-4-methylchromen-2-one
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: LTRVCAVJHXZWAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-acetyl-3-ethyl-7-hydroxy-4-methyl-2H-chromen-2-one 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-6-[3-(4-dimethylaminophenyl)acryloyl]-3-ethyl-7-methoxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization

  摘要：

  A series of two-photon (TP) active 4-dimethylaminocinnamoyl coumarins were synthesized. These compounds exhibit red shift in absorption and considerable Stokes shift in emission spectra in comparison to the parent coumarin. Large TP absorption cross-sections were measured for all the coumarins in dilute solutions. A correlation between the chemical structure and TP characteristics was established. TP confocal microscopy revealed that these coumarin derivatives can be internalized by cancer cells rendering them a potential candidate as a label in TP confocal imaging. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2014.02.005
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 6-acetyl-3-ethyl-7-hydroxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.11.016

文献信息

• Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl- and pyranochromen-2-one derivatives
  作者：Karam Chand、Amir Nasrolahi Shirazi、Preeti Yadav、Rakesh K. Tiwari、Meena Kumari、Keykavous Parang、Sunil K. Sharma

  DOI：10.1139/cjc-2013-0053

  日期：2013.8

  8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with

  合成了一系列 6- 和 8-cinnamoylchromen-2-one 和 dihydropyranochromen-2-one 衍生物，并评估了它们对三种人类癌细胞系的抗增殖活性，即卵巢腺癌 (SK-OV-3)、白血病 (CCRF) -CEM) 和乳腺癌 (MCF-7)。一般而言，与 6-肉桂酰类似物相比，8-cinnamoylchromen-2-one 衍生物对癌细胞具有更高的抗增殖活性。在所有杂合 chromen-2-one - 查尔酮/黄烷酮化合物中，发现 7-hydroxy-8-cinnamoylchromen-2-one 衍生物 35 对所有癌细胞系均具有持续活性并抑制 SK-的细胞增殖OV-3、CCRF-CEM 和 MCF-7 在孵育 72 小时后浓度为 50 μmol/L 时分别增加 63%、50% 和 43%。该化合物还表现出最高的 Src 激酶抑制 (IC50 = 14
• 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 of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization
  作者：Preeti Yadav、Soumitra Satapathi、Meena Kumari、Akanksha Chaturvedi、Lian Li、Lynne A. Samuelson、Jayant Kumar、Sunil K. Sharma

  DOI：10.1016/j.jphotochem.2014.02.005

  日期：2014.4

  A series of two-photon (TP) active 4-dimethylaminocinnamoyl coumarins were synthesized. These compounds exhibit red shift in absorption and considerable Stokes shift in emission spectra in comparison to the parent coumarin. Large TP absorption cross-sections were measured for all the coumarins in dilute solutions. A correlation between the chemical structure and TP characteristics was established. TP confocal microscopy revealed that these coumarin derivatives can be internalized by cancer cells rendering them a potential candidate as a label in TP confocal imaging. (C) 2014 Elsevier B.V. All rights reserved.