1-[3-Acetyl-4-hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)phenyl]ethanone | 1148140-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-Acetyl-4-hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)phenyl]ethanone
• 英文别名: 1-[3-acetyl-4-hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)phenyl]ethanone
• CAS: 1148140-36-6
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: DSTMPJFGZICWDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-苄氧基苯甲醛 、 1-[3-Acetyl-4-hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)phenyl]ethanone 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以92%的产率得到(2E,2'E)-1,1'-(4'-benzyloxy-3-hydroxy-5-methylbiphenyl-2,6-diyl)bis(3-(4-benzyloxyphenyl)prop-2-en-1-one)
  参考文献：
  名称：

  Synthesis and anti breast cancer activity of biphenyl based chalcones

  摘要：

  A series of (2E,2'E)-1,1'-(3-hydroxy-5-methylbiphenyl-2,6-diyl)-bis(3-pheylprop-2-ene-1-ones (5-33) were prepared by the reaction of 1,3-diacetyl biphenyls (1-4) with different aldehydes in presence of catalytic amount of solid KOH in ethanol in excellent yields. The compounds were evaluated for anticancer activity against human breast cancer MCF-7 (estrogen responsive proliferative breast cancer model) and MDA-MB-231 (estrogen independent aggressive breast cancer model) cell lines, HeLa (cervical cancer) cell line, and human embryonic kidney (HEK-293) cells. Most of the compounds preferentially inhibited the growth of the aggressive human breast cancer cell lines, MDA-MB-231 in the range of 4.4-30 mu M. The two compounds 9 and 29 proved to be better anticancer agents than the standard drug tamoxifen against the MDA-MB-231 cell lines. Mode of action of these compounds was established to be apoptosis, cell cycle arrest and loss of mitochondrial membrane potential. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.015
• 作为产物：
  描述：

  2,4-Diacetyl-5-hydroxy-5-methyl-3-(4-phenylmethoxyphenyl)cyclohexan-1-one 在 碘 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以55%的产率得到1-[3-Acetyl-4-hydroxy-6-methyl-2-(4-phenylmethoxyphenyl)phenyl]ethanone
  参考文献：
  名称：

  通过芳族醛与β-酮酸酯或酮的顺序反应有效地选择性合成官能化联苯

  摘要：

  芳族醛和β-酮酯/酮的Knoevenagel / Michael / Aldol反应以连续的方式以良好的收率得到中间体环己酮。后者在用碘进行氧化芳构化后，以中等至良好的产率获得了具有至少一个酚羟基的官能化联苯。

  DOI：

  10.1016/j.tetlet.2009.02.001

文献信息

• An efficient regioselective synthesis of functionalized biphenyls via sequential reactions of aromatic aldehydes and β-keto esters or ketones
  作者：Anindra Sharma、Jyoti Pandey、R.P. Tripathi

  DOI：10.1016/j.tetlet.2009.02.001

  日期：2009.4

  Knoevenagel/Michael/Aldol reactions of aromatic aldehydes and β-keto esters/ketones in a sequential manner yielded intermediate cyclohexanones in good yields. The latter, on oxidative aromatization with iodine, afforded functionalized biphenyls with at least one phenolic hydroxyl in moderate to good yields.

  芳族醛和β-酮酯/酮的Knoevenagel / Michael / Aldol反应以连续的方式以良好的收率得到中间体环己酮。后者在用碘进行氧化芳构化后，以中等至良好的产率获得了具有至少一个酚羟基的官能化联苯。
• Synthesis and anti breast cancer activity of biphenyl based chalcones
  作者：Anindra Sharma、Bandana Chakravarti、Munna Prasad Gupt、Jawed A. Siddiqui、Rituraj Konwar、Rama P. Tripathi

  DOI：10.1016/j.bmc.2010.05.015

  日期：2010.7

  A series of (2E,2'E)-1,1'-(3-hydroxy-5-methylbiphenyl-2,6-diyl)-bis(3-pheylprop-2-ene-1-ones (5-33) were prepared by the reaction of 1,3-diacetyl biphenyls (1-4) with different aldehydes in presence of catalytic amount of solid KOH in ethanol in excellent yields. The compounds were evaluated for anticancer activity against human breast cancer MCF-7 (estrogen responsive proliferative breast cancer model) and MDA-MB-231 (estrogen independent aggressive breast cancer model) cell lines, HeLa (cervical cancer) cell line, and human embryonic kidney (HEK-293) cells. Most of the compounds preferentially inhibited the growth of the aggressive human breast cancer cell lines, MDA-MB-231 in the range of 4.4-30 mu M. The two compounds 9 and 29 proved to be better anticancer agents than the standard drug tamoxifen against the MDA-MB-231 cell lines. Mode of action of these compounds was established to be apoptosis, cell cycle arrest and loss of mitochondrial membrane potential. (C) 2010 Elsevier Ltd. All rights reserved.