3-ethyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl acetate

• 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-ethyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl acetate
• 英文别名: 3-ethyl-7-acetoxy-4-methylcoumarin；7-acetoxy-3-ethyl-4-methyl-coumarin；7-Acetoxy-3-aethyl-4-methyl-cumarin；3-ethyl-4-methyl-2-oxo-2H-chromen-7-yl acetate；(3-ethyl-4-methyl-2-oxochromen-7-yl) acetate
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: LAWDEVOZKAFFJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl acetate 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 8-cinnamoyl-3-ethyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis, docking and in vitro anticancer evaluation of some new benzopyrone derivatives

  摘要：

  The synthesis of some new 3-alkyl-7-hydroxy-4-methyl-8-substituted-1H-benzopyran-2-ones, 6-alkyl-7-methyl-2-substituted amino-5H-pyrano[6,5-e] benzoxazol-5-ones, 7-alkyl-8-methyl-3-substituted-2,6-dihydropyrano[6,5-f]-1,4-benzoxazin-6-ones, 7,8-disubstituted-3-ethyl-4-methyl-1H-benzopyran-2-ones and 3-alkyl-4-methyl-7-substituted-1H-benzopyran-2-ones were described. Fourteen compounds were selected by National Cancer Institute (NCI), Bethesda, and evaluated for their in vitro anticancer activity in the full NCI 60 cell lines panel assay by a single dose test. Compounds 4a, 18a, 18b and 23a were found to be broad-spectrum antitumors showing effectiveness toward numerous cell lines that belong to different tumor subpanels. Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the binding site of the casein kinase II (CK2) enzyme which is involved in cell survival and proliferation through a number of downstream effectors. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.02.003
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 4-二甲氨基吡啶 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 3-ethyl-4-methyl-2-oxo-2H-1-benzopyran-7-yl acetate
  参考文献：
  名称：

  cinnamoyl-和pyranochromen-2-one衍生物的合成和抗增殖和c-Src激酶抑制活性

  摘要：

  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

  DOI：

  10.1139/cjc-2013-0053

文献信息

• Specificities of Calreticulin Transacetylase to acetoxy derivatives of 3-alkyl-4-methylcoumarins: Effect on the activation of nitric oxide synthase
  作者：Abha Kathuria、Anjali Gupta、Nivedita Priya、Prabhjot Singh、Hanumantharao G. Raj、Ashok K. Prasad、Virinder S. Parmar、Sunil K. Sharma

  DOI：10.1016/j.bmc.2009.01.003

  日期：2009.2

  the C-3 position of the acetoxy coumarins on the CRTAase activity. The substitution at C-3 position of coumarin nucleus resulted in the reduction of CRTAase activity and related effects. Accordingly the formation of NO in platelets by C-3 alkyl substituted acetoxy coumarins was found to be much less compared to the unsubstituted analogs. In addition the alkyl substitution at C-3 position exhibited the

  钙网蛋白转乙酰酶（CRTAase）催化乙酰基从多酚乙酸酯（PAs）转移至受体蛋白并调节其生物学活性。通过对胞质谷胱甘肽S的不可逆抑制可以方便地测定CRTAase-乙酰转移酶（GST）由模型乙酰氧基香豆素，7,8-二乙酰氧基-4-甲基香豆素（DAMC）制成。我们之前已经研究过乙酰氧基对苯环的影响，C-3和C-4位双键还原的影响，C-4位甲基/苯基的影响以及C-4位的影响。苯并吡喃核中相对于氧杂原子的羰基，具有CRTAase的催化活性。在本次交流中，我们扩展了以前的工作；其中我们研究了乙酰氧基香豆素C-3位置的烷基（乙基，己基和癸基）对CRTAase活性的影响。香豆素核的C-3位取代导致CRTAase活性降低和相关作用。因此，发现与未取代的类似物相比，由C-3烷基取代的乙酰氧基香豆素在血小板中NO的形成要少得多。另外，在C-3位的烷基取代表现出形成除NO以外的自由基的趋势。
• 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.
• Canter et al., Journal of the Chemical Society, 1931, p. 1255,1264
  作者：Canter et al.

  DOI：——

  日期：——
• 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.
• Chakravarti, Journal of the Indian Chemical Society, 1931, vol. 8, p. 129,132
  作者：Chakravarti

  DOI：——

  日期：——