3-(4-hydroxyphenyl)-4,6-diphenyl-pyran-2-one | 1172584-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(4-hydroxyphenyl)-4,6-diphenyl-pyran-2-one
• 英文别名: 3-(4-Hydroxyphenyl)-4,6-diphenylpyran-2-one
• CAS: 1172584-23-4
• 化学式: C₂₃H₁₆O₃
• 分子量: 340.378
• InChiKey: JZPVXCBWJVTLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-4,6-diphenyl-pyran-2-one 、 1-(2-氯乙基)哌啶盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到4,6-diphenyl-3-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-pyran-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents

  摘要：

  A series of 3,4,6-triaryl-2-pyranones, new class of anti-breast cancer agents, have been synthesized as a structural variants of cyclic triphenylethylenes by replacing the fused benzene ring with pendant phenyl ring to mimic the phenolic A ring of estradiol. Nine of these newly synthesized pyranones exhibited significant anti-proliferative activity in both ER+ve and ER-ve breast cancer cell lines. Four active non-cytotoxic compounds 5c, 5d, 5g and 5h showed specific and selective cytotoxicity and two compounds 5d and 5h induced significant DNA fragmentation in both MCF-7 and MDA-MB-231 cell lines. Based on RBA studies, the molecules probably act in an ER-independent mechanism. The involved pathway was observed as caspase-dependant apoptosis in MCF-7 cells. However, the particular caspases involved and the possible cellular target through which this series of compounds mediate cell death are not known. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.032
• 作为产物：
  描述：

  3-(4-methoxyphenyl)-4,6-diphenyl-2H-pyran-2-one 在 吡啶盐酸盐 作用下， 反应 2.0h， 以72%的产率得到3-(4-hydroxyphenyl)-4,6-diphenyl-pyran-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents

  摘要：

  A series of 3,4,6-triaryl-2-pyranones, new class of anti-breast cancer agents, have been synthesized as a structural variants of cyclic triphenylethylenes by replacing the fused benzene ring with pendant phenyl ring to mimic the phenolic A ring of estradiol. Nine of these newly synthesized pyranones exhibited significant anti-proliferative activity in both ER+ve and ER-ve breast cancer cell lines. Four active non-cytotoxic compounds 5c, 5d, 5g and 5h showed specific and selective cytotoxicity and two compounds 5d and 5h induced significant DNA fragmentation in both MCF-7 and MDA-MB-231 cell lines. Based on RBA studies, the molecules probably act in an ER-independent mechanism. The involved pathway was observed as caspase-dependant apoptosis in MCF-7 cells. However, the particular caspases involved and the possible cellular target through which this series of compounds mediate cell death are not known. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.032

文献信息

• Synthesis and biological evaluation of 3,4,6-triaryl-2-pyranones as a potential new class of anti-breast cancer agents
  作者：Ravi Shankar、Bandana Chakravarti、Uma Sharan Singh、Mohd. Imran Ansari、Shreekant Deshpande、Shailendra Kumar Dhar Dwivedi、Hemant Kumar Bid、Rituraj Konwar、Geetika Kharkwal、Vishal Chandra、Anila Dwivedi、K. Hajela

  DOI：10.1016/j.bmc.2009.04.032

  日期：2009.6

  A series of 3,4,6-triaryl-2-pyranones, new class of anti-breast cancer agents, have been synthesized as a structural variants of cyclic triphenylethylenes by replacing the fused benzene ring with pendant phenyl ring to mimic the phenolic A ring of estradiol. Nine of these newly synthesized pyranones exhibited significant anti-proliferative activity in both ER+ve and ER-ve breast cancer cell lines. Four active non-cytotoxic compounds 5c, 5d, 5g and 5h showed specific and selective cytotoxicity and two compounds 5d and 5h induced significant DNA fragmentation in both MCF-7 and MDA-MB-231 cell lines. Based on RBA studies, the molecules probably act in an ER-independent mechanism. The involved pathway was observed as caspase-dependant apoptosis in MCF-7 cells. However, the particular caspases involved and the possible cellular target through which this series of compounds mediate cell death are not known. (C) 2009 Elsevier Ltd. All rights reserved.