(2E,2'E)-1,1'-(4'-chloro-3-hydroxy-5-methylbiphenyl-2,6-diyl)bis(3-(4-chlorophenyl)prop-2-en-1-one) | 1236464-40-6

• 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: (2E,2'E)-1,1'-(4'-chloro-3-hydroxy-5-methylbiphenyl-2,6-diyl)bis(3-(4-chlorophenyl)prop-2-en-1-one)
• 英文别名: (E)-3-(4-chlorophenyl)-1-[2-(4-chlorophenyl)-3-[(E)-3-(4-chlorophenyl)prop-2-enoyl]-4-hydroxy-6-methylphenyl]prop-2-en-1-one
• CAS: 1236464-40-6
• 化学式: C₃₁H₂₁Cl₃O₃
• 分子量: 547.865
• InChiKey: LXOHAYYXCPDCKT-KGMKFKQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-[3-Acetyl-2-(4-chlorophenyl)-4-hydroxy-6-methylphenyl]ethanone 、 4-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以95%的产率得到(2E,2'E)-1,1'-(4'-chloro-3-hydroxy-5-methylbiphenyl-2,6-diyl)bis(3-(4-chlorophenyl)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

文献信息

• 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.