(E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl) prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl) prop-2-en-1-one
• 英文别名: (2E)-3-(2,3-Dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one；(E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: RKFUYVPHYBKMSJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲基-2-乙酰基呋喃 、 2,3-二甲氧基苯甲醛 在 alkali hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以82%的产率得到(E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl) prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and cytotoxic effects of (E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl) prop-2-en-1-one in MDA-MB231 and MCF-7 breast cancer cell lines

  摘要：

  A chalcone derivative, (E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)-prop-2-en-1-one (DMMF) was synthesized and evaluated against various cancerous cell lines including colon adenocarcinoma (HT29), myloplasticleukemia (HL60), breast cancer (MCF-7 and MDA-MB231), normal hepatic cell (WRL-68) and normal breast cell (MCF-10A). The structure of DMMF was determined by EI-MS, H-1 NMR and single X-ray crystallographic techniques. The DMMF possessed the highest cytotoxic effect against MCF-7 breast cancer cell (2.01 +/- 1.53 mu g/mL) and lowest against normal hepatic WRL-68 and breast cell lines after 24 h of treatment. Induction of apoptosis and regulation of cell cycle progression results indicates the significant increase in early apoptosis and G2/M arrest after 48 h of treatment in MCF-7 cells. Meanwhile, in MDA-MB231 cells, there was an increase in Sub G0/G1 cells population and early/late apoptotic cells upon treatment with DMMF. Additionally, DMMF effectively induced G2/M cell cycle arrest in MCF-7 cells and apoptosis in both MCF-7 and MDA-MB231 cells. (C) 2016 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytol.2016.12.022

文献信息

• Synthesis and cytotoxic effects of (E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl) prop-2-en-1-one in MDA-MB231 and MCF-7 breast cancer cell lines
  作者：Muhammad Nadeem Akhtar、Landa Zeenelabdin Ali Salim、Swee Keong Yeap、Nadiah Abu、Seema Zareen、Kong Mun Lo、Addila abu Bakar、Noorjahan Banu Alitheen

  DOI：10.1016/j.phytol.2016.12.022

  日期：2017.3

  A chalcone derivative, (E)-3-(2,3-dimethoxyphenyl)-1-(5-methylfuran-2-yl)-prop-2-en-1-one (DMMF) was synthesized and evaluated against various cancerous cell lines including colon adenocarcinoma (HT29), myloplasticleukemia (HL60), breast cancer (MCF-7 and MDA-MB231), normal hepatic cell (WRL-68) and normal breast cell (MCF-10A). The structure of DMMF was determined by EI-MS, H-1 NMR and single X-ray crystallographic techniques. The DMMF possessed the highest cytotoxic effect against MCF-7 breast cancer cell (2.01 +/- 1.53 mu g/mL) and lowest against normal hepatic WRL-68 and breast cell lines after 24 h of treatment. Induction of apoptosis and regulation of cell cycle progression results indicates the significant increase in early apoptosis and G2/M arrest after 48 h of treatment in MCF-7 cells. Meanwhile, in MDA-MB231 cells, there was an increase in Sub G0/G1 cells population and early/late apoptotic cells upon treatment with DMMF. Additionally, DMMF effectively induced G2/M cell cycle arrest in MCF-7 cells and apoptosis in both MCF-7 and MDA-MB231 cells. (C) 2016 Phytochemical Society of Europe. Published by Elsevier Ltd. All rights reserved.