(E)-8-[3-(3,4-dimethoxyphenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one | 148304-10-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-8-[3-(3,4-dimethoxyphenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one
• 英文别名: 8-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-7-hydroxy-4-methylchromen-2-one
• CAS: 148304-10-3
• 化学式: C₂₁H₁₈O₆
• 分子量: 366.37
• InChiKey: UJNOJIPDRNVLCM-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-8-[3-(3,4-dimethoxyphenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.57h， 以80%的产率得到4-chloro-8-methyl-2-(3,4-dimethoxyphenyl)-1,5-dioxa-2H-phenanthren-6-one
  参考文献：
  名称：

  Microwave-assisted synthesis of substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones and their antimicrobial activity

  摘要：

  Chromene and coumarin scaffolds are known for their potential antimicrobial activity. Herein, we have synthesized hybrid compounds containing both, substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones, 3a-o have been synthesized from substituted (E)-1-(7-Hydroxy-4-methyl-8-coumarinyl)-3-phenyl-2-propen-1-ones, 2a-o in good yield using the microwave-assisted Vilsmeier-Haack reaction. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 3e, 3f and 3g were found to be potent against tested fungal and bacterial strains.

  DOI：

  10.1007/s00044-014-1204-9
• 作为产物：
  描述：

  8-乙酰-7-甲氧基香豆素 在 氢氧化钾 、 三氯化铝 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 14.5h， 生成 (E)-8-[3-(3,4-dimethoxyphenyl)acryloyl]-7-hydroxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Ahluwalia, V. K.; Nayal, Lalita; Tehim, A. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 70 - 71

  摘要：

  DOI：

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
• Microwave-assisted synthesis of (<i>E</i>)-7-[(1-benzyl-1<i>H</i>-1,2,3-triazol-4-yl)methoxy]-8-(3-arylacryloyl)-4-methyl-2<i>H</i>-chromen-2-ones and their antimicrobial activity
  作者：Ashok Dongamanti、Vijaya Lakshmi Bommidi、Ganesh Arram、Ravi Sidda

  DOI：10.1515/hc-2014-0102

  日期：2014.10.1

  Hybrid compounds are relevant products in the structure-activity relationships analysis. A new series of hybrid compounds containing coumarin, 1,2,3-triazole, and chalcone substructures were synthesized and screened for their antimicrobial activity. The structures of the synthesized compounds have been established on the basis of analytical and spectral data.

  混合化合物是结构活性关系分析中相关的产品。合成了一系列含有香豆素、1,2,3-三唑和香豜素亚结构的混合化合物，并对它们的抗菌活性进行了筛选。合成化合物的结构已根据分析和光谱数据确定。

• Khan, M. S. Y.; Sharma, Poonam, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 374 - 376
  作者：Khan, M. S. Y.、Sharma, Poonam

  DOI：——

  日期：——
• SYNTHESIS OF SOME NEW 1,5-BENZOTHIAZEPINES CONTAINING 2H-1- BENZOPYRAN-2-ONE HETEROCYCLE
  作者：A. Prashant、S. Srinivas Rao、K.S. Chowdary、V.S.H. Krishnan

  DOI：10.1515/hc.2001.7.1.61

  日期：2001.1
• Khan; Mueed, M. Asad, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 8, p. 1794 - 1797
  作者：Khan、Mueed, M. Asad

  DOI：——

  日期：——