(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one | 1607-73-4

• 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)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one；3'-bromo-4,4',6'-trimethoxy-2'-hydroxy-chalcone；5'-bromo-6'-hydroxy-4.2'.4'-trimethoxy-trans-chalcone；5'-Brom-6'-hydroxy-4.2'.4'-trimethoxy-trans-chalkon；(E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 1607-73-4；94103-34-1
• 化学式: C₁₈H₁₇BrO₅
• 分子量: 393.234
• InChiKey: ATIOPZIMMBXWPT-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 以65%的产率得到
  参考文献：
  名称：

  ALI, SYED, MASHHOOD;IQBAL, JAWAID;HYAS, MOHD, CHEM. AND IND., 1985, N 8, 276

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(2-羟基-4,6-二甲氧基苯基)-3-(4-甲氧基苯基)-2-丙烯-1-酮 在 四丁基溴化铵 、 双氧水 、 vanadia 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  V2O5-H2O2促进的四丁基溴化铵对有机底物的区域选择性溴化：对环境有利的合成方案

  摘要：

  [反应：见正文]在过氧化氢的存在下，五氧化二钒非常有效地促进了四丁基溴化铵对有机底物的溴化作用，包括对某些芳族化合物的选择性溴化作用；温和的条件，高的选择性，收率和反应速率，以及溴和氢溴酸的冗余是合成方案的一些主要优点。

  DOI：

  10.1021/ol9902935

文献信息

• Regioselective Bromination of Organic Substrates by Tetrabutylammonium Bromide Promoted by V₂O₅−H₂O₂:  An Environmentally Favorable Synthetic Protocol
  作者：Upasana Bora、Gopal Bose、Mihir K. Chaudhuri、Siddhartha S. Dhar、Rangam Gopinath、Abu T. Khan、Bhisma K. Patel

  DOI：10.1021/ol9902935

  日期：2000.2.1

  [reaction: see text] Vanadium pentoxide very effectively promotes the bromination of organic substrates, including selective bromination of some aromatics, by tetrabutylammonium bromide in the presence of hydrogen peroxide; mild conditions, high selectivity, yield, and reaction rate, and redundancy of bromine and hydrobromic acid are some of the major advantages of the synthetic protocol.

  [反应：见正文]在过氧化氢的存在下，五氧化二钒非常有效地促进了四丁基溴化铵对有机底物的溴化作用，包括对某些芳族化合物的选择性溴化作用；温和的条件，高的选择性，收率和反应速率，以及溴和氢溴酸的冗余是合成方案的一些主要优点。
• Hydroxychalcones induce apoptosis in B16-F10 melanoma cells via GSH and ATP depletion
  作者：Andréia Lilian Formento Navarini、Louise Domeneghini Chiaradia、Alessandra Mascarello、Márcio Fritzen、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.ejmech.2008.09.009

  日期：2009.4

  Searching for leading compounds of new drugs for cancer therapy, we studied the toxicity of 13 hydroxychalcones never tested before toward melanoma cell line (B16-F10). The compounds were obtained by aldolic condensation between aldehydes and hydroxylated acetophenones, in alkaline conditions. Three of them showed cytotoxicity to the cell line. Two of them induced mitochondrial GSH and ATP depletion and promoted cell death through apoptosis in melanoma cells. One of the compounds induced cell death through necrosis but did not significantly decrease the intracellular mitochondrial GSH and ATP levels in melanoma cells. The results suggest that the predominant factor for the activity is the molecule shape, and secondarily the number of hydroxyl groups. (c) 2008 Published by Elsevier Masson SAS.
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.
• Synthesis and biological evaluation of novel series of chalcone derivatives as inhibitors of cyclooxygenase and LPS-induced TNF-α with potent antioxidant properties
  作者：Babasaheb P. Bandgar、Baliram S. Hote、Nagesh A. Dhole、Rajesh N. Gacche

  DOI：10.1007/s00044-011-9746-6

  日期：2012.9

  Novel series of chalcones were synthesized and were evaluated as possible anti-inflammatory agents targeting the cyclooxygenase-1 and 2 (COX-1 and 2), beta-glucuronidase, trypsin, and TNF-alpha. Amongst the tested chalcones the compound 4k was found to be most effective inhibitor of TNF-alpha exhibiting 85% inhibition activity (IC50 = 0.1 mu M). The compounds 4a, 4f, 4l, and 4m were found to inhibit the COX-1 activity in as a range of 79.95-68.47% and COX-2 inhibition ranging 84.45-74.77%. The compounds 4l (81.71%) and 4f (72.10%) were found to be excellent inhibitors of trypsin and beta-glucuronidase, respectively.
• 17. Chalkones: a new synthesis of chrysin, apigenin, and luteolin
  作者：W. A. Hutchins、T. S. Wheeler

  DOI：10.1039/jr9390000091

  日期：——