Cyclopropyl-(2,4,6-trihydroxyphenyl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cyclopropyl-(2,4,6-trihydroxyphenyl)methanone
• 英文别名: cyclopropyl-(2,4,6-trihydroxyphenyl)methanone
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: ZDYAMTRDSWTTMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cyclopropyl-(2,4,6-trihydroxyphenyl)methanone 、 1-溴-3-甲基-2-丁烯 在 氨 作用下， 以 乙醚 为溶剂， 以24%的产率得到
  参考文献：
  名称：

  The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells

  摘要：

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.11.011
• 作为产物：
  描述：

  间苯三酚 、 环丙基甲酰氯 在 aluminum (III) chloride 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 以66%的产率得到Cyclopropyl-(2,4,6-trihydroxyphenyl)methanone
  参考文献：
  名称：

  The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells

  摘要：

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.11.011

文献信息

• 2,4-Diacetylphloroglucinol (DAPG) derivatives rapidly eradicate methicillin-resistant staphylococcus aureus without resistance development by disrupting membrane
  作者：Yifan Zhong、Xiaoli He、Wenlan Tao、Jizhou Feng、Ruixue Zhang、Hongzhi Gong、Ziyi Tang、Chao Huang、Yun He

  DOI：10.1016/j.ejmech.2023.115823

  日期：2023.12

  Methicillin-resistant Staphylococcus aureus (MRSA) causes severe public health challenges throughout the world, and the multi-drug resistance (MDR) of MRSA to antibiotics necessitates the development of more effective antibiotics. Natural 2,4-diacetylphloroglucinol (DAPG), produced by Pseudomonas, displays moderate inhibitory activity against MRSA. A series of DAPG derivatives was synthesized and evaluated

  耐甲氧西林金黄色葡萄球菌（MRSA）给全世界带来了严峻的公共卫生挑战，而MRSA对抗生素的多重耐药性（MDR）使得开发更有效的抗生素成为必要。天然 2,4-二乙酰基间苯三酚 (DAPG) 由假单胞菌产生，对 MRSA 显示出中等的抑制活性。合成了一系列 DAPG 衍生物并对其抗菌活性进行了评估，其中一些表现出优异的活性（MRSA MIC = 0.5–2 μg/mL）。在这些衍生物中，7g表现出很强的抗菌活性，两个月内未出现耐药性。机理研究表明7g通过靶向细菌细胞膜发挥其活性。此外，7g与苯唑西林在体外和体内均表现出显着的协同抗菌作用，并具有根除MRSA生物膜的趋势。7g是治疗 MRSA 的一种有前景的先导药物。
• The synthesis and anticancer effects of a range of natural and unnatural hop β-acids on breast cancer cells
  作者：Elizabeth Tyrrell、Roland Archer、Matt Tucknott、Kay Colston、Grisha Pirianov、Dharahana Ramanthan、Rajdeep Dhillon、Alex Sinclair、G.A. Skinner

  DOI：10.1016/j.phytol.2011.11.011

  日期：2012.3

  The beta-acids derived from hops (Humulus lupulus L.) are polyphenols classified as lupulones. As part of our on-going interest in the pharmacognosy of these natural products we were keen to investigate the anticancer activity of lupulone 1 as well as individual lupulone congeners. To achieve this we undertook the synthesis of natural as well as unnatural lupulone derivatives and evaluated them for their anticancer activity against the breast cancer cell lines MCF-7 and MDA-MB-231.The results of our investigations revealed that all of the novel unnatural lupulone derivatives that were synthesised were found to be more toxic to MDA-MB-231 cell lines at 72 h than the parent lupulone 1 itself (except for the alpha-substituent R-1 was CH3). Further investigations confirmed that the novel lupulone derivatives were very efficient at killing cancer cells by apoptosis but appear to do so in a time-dependant process. This outcome may be of great significance as MDA-MB-231 cell lines are characterised by an aggressive phenotype with a propensity to invade other tissue, to form metastases as well as an ability to become insensitive to chemotherapeutic agents. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.