2'-hydroxy-2,3,4',6'-tetramethoxychalcone | 76554-75-1

• 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: 2'-hydroxy-2,3,4',6'-tetramethoxychalcone
• 英文别名: HTMC；2-Hydroxy-4.6.2'.3'-tetramethoxy-chalkon；2'Hydroxy-2,3,4',6'-tetramethoxychalcone；3-(2,3-dimethoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• CAS: 76554-75-1
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: LYUYMCWIWGASRX-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  558.5±50.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-2,3,4',6'-tetramethoxychalcone 在 三氯化铝 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 7.0h， 生成 5-hydroxy-7,2',3'-trimethoxyflavanone
  参考文献：
  名称：

  Synthesis, growth inhibition, and cell cycle evaluations of novel flavonoid derivatives

  摘要：

  As a continuation of our search for potential new anticancer agents, a series of ten flavonoid derivatives has been synthesized by cyclization of substituted chalcones. Target compounds were evaluated for their biological activity. Among them, compounds 1-4 and 9 displayed a significant growth inhibitory action against a panel of tumor cell lines including Jurkat, PC-3, and Colon 205. On treatment with an equitoxic (IC50) concentration, compounds 1-5 and 7-9 blocked cells in the G2/M phase of the Jurkat cell cycle, whereas compound 6 blocked the same in the G0/G1 phase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.062
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 2,3-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 49.0h， 以88%的产率得到2'-hydroxy-2,3,4',6'-tetramethoxychalcone
  参考文献：
  名称：

  Chalcone HTMC causes in vitro selective cytotoxicity, cell-cycle G1 phase arrest through p53-dependent pathway in human lung adenocarcinoma A549 cells, and in vivo tumor growth suppression

  摘要：

  The present Letter identified 2'-hydroxy-2,3,4',6'-tetramethoxychalcone (HTMC) as a potent in vitro cytotoxic agent with selective activity against cell lines derived from human lung cancer. In A549 lung adenocarcinoma cells, HTMC caused G1 phase cell-cycle arrest. HTMC treatment also led to an inhibition of cell-cycle regulatory proteins phosphorylation of cdc2 (Tyr(15) and Tyr(161)) and Rb (Ser(795) and Ser(807/811)), which was accompanied by the accumulation of tumor suppresser genes p53 and p21. In addition, in vivo data demonstrated that HTMC act as a tumor growth suppressing agent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.056

文献信息

• Identification of small molecule inhibitors of telomerase activity through transcriptional regulation of hTERT and calcium induction pathway in human lung adenocarcinoma A549 cells
  作者：Yerra Koteswara Rao、Te-Yu Kao、Ming-Fang Wu、Jiunn-Liang Ko、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2010.08.021

  日期：2010.10

  High telomerase activity (TA) is detected in most cancer cells; and thus, TA inhibition by drug or dietary food components is a new strategy for cancer prevention. In this report, we examined the effects of fourteen natural or synthetic compounds on TA in human lung adenocarcinoma A549 cells. The results demonstrated that some of the tested compounds inhibited TA, being 2'-hydroxy-2,3,4',6'-tetramethoxy-chalcone (HTMC) was the most potent among tested. In A549 cells, HTMC also inhibited the cell proliferation, decreased the expression of human telomerase reverse transcriptase (hTERT) and sequentially reduced the hTERT promoter. In soft agar assay HTMC treatment reduced the colony formation of A549 cells. Cellular fractionation and immunofluorescence assay demonstrated that there was no translocation of hTERT from nuclei to cytoplasm. Further studies revealed that the release of Ca2+ was the underlying mechanism of suppressed TA and hTERT transcription in A549 cells exposed to HTMC. These in vitro data support the development of HTMC as a therapeutic agent for cancer complications. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, growth inhibition, and cell cycle evaluations of novel flavonoid derivatives
  作者：Yerra Koteswara Rao、Shih-Hua Fang、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2005.07.062

  日期：2005.12

  As a continuation of our search for potential new anticancer agents, a series of ten flavonoid derivatives has been synthesized by cyclization of substituted chalcones. Target compounds were evaluated for their biological activity. Among them, compounds 1-4 and 9 displayed a significant growth inhibitory action against a panel of tumor cell lines including Jurkat, PC-3, and Colon 205. On treatment with an equitoxic (IC50) concentration, compounds 1-5 and 7-9 blocked cells in the G2/M phase of the Jurkat cell cycle, whereas compound 6 blocked the same in the G0/G1 phase. (c) 2005 Elsevier Ltd. All rights reserved.
• Chalcone HTMC causes in vitro selective cytotoxicity, cell-cycle G1 phase arrest through p53-dependent pathway in human lung adenocarcinoma A549 cells, and in vivo tumor growth suppression
  作者：Yerra Koteswara Rao、Te-Yu Kao、Jiunn-Liang Ko、Yew-Min Tzeng

  DOI：10.1016/j.bmcl.2010.09.056

  日期：2010.11

  The present Letter identified 2'-hydroxy-2,3,4',6'-tetramethoxychalcone (HTMC) as a potent in vitro cytotoxic agent with selective activity against cell lines derived from human lung cancer. In A549 lung adenocarcinoma cells, HTMC caused G1 phase cell-cycle arrest. HTMC treatment also led to an inhibition of cell-cycle regulatory proteins phosphorylation of cdc2 (Tyr(15) and Tyr(161)) and Rb (Ser(795) and Ser(807/811)), which was accompanied by the accumulation of tumor suppresser genes p53 and p21. In addition, in vivo data demonstrated that HTMC act as a tumor growth suppressing agent. (C) 2010 Elsevier Ltd. All rights reserved.