(E)-3-(2-bromophenyl)-1-(2'-hydroxyphenyl)prop-2-en-1-one | 55370-65-5

• 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: (E)-3-(2-bromophenyl)-1-(2'-hydroxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(2-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one；2-bromo-2'-hydroxy-trans-chalcone；2-Brom-2'-hydroxy-trans-chalkon；2-Propen-1-one, 3-(2-bromophenyl)-1-(2-hydroxyphenyl)-
• CAS: 55370-65-5；145626-25-1
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: NTNRRUWBUFUMCG-MDZDMXLPSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  442.5±45.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-bromophenyl)-1-(2'-hydroxyphenyl)prop-2-en-1-one 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 copper(II) oxide 作用下， 反应 4.0h， 生成 10,11-Dihydrobenzo[b][1]benzoxocin-12-one
  参考文献：
  名称：

  Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

  摘要：

  Microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling is described. Using the optimized conditions, a panel of macrocycles, with different substitution patterns, ring sizes, and linkers, has been successfully synthesized using microwave irradiation. To the best of our knowledge, this work represents the first examples of the microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.142
• 作为产物：
  描述：

  3-(2-Bromo-phenyl)-3-hydroxy-1-(2-hydroxy-phenyl)-propan-1-one 在 oxonium 作用下， 生成 (E)-3-(2-bromophenyl)-1-(2'-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of 4,6-disubstituted 3-cyanopyridin-2(1H)-ones, a new class of calcium entry blockers

  摘要：

  The preparation of 3-cyano-4,6-diaryl-pyridin-2(1H)-ones 4a . h, calcium entry blockers related to diltiazem, is described starting from 1,3-diaryl-2-propen-1-ones 5. On preliminary pharmacological tests all compounds are active and some of them show calcium antagonistic activity superior or comparable to diltiazem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00361-9

文献信息

• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。
• Halo-Substituted Chalcones and Azachalcones Inhibited Lipopolysaccharited-Stimulated Pro-Inflammatory Responses through the TLR4-Mediated Pathway
  作者：Tzenge-Lien Shih、Ming-Hwa Liu、Chia-Wai Li、Chia-Feng Kuo

  DOI：10.3390/molecules23030597

  日期：——

  A series of B-ring, halo-substituted chalcones and azachalcones were synthesized to evaluate and compare their anti-inflammatory activity. Mouse BALB/c macrophage RAW 264.7 were pre-treated with 10 μg/mL of each compound for one hour before induction of inflammation by lipopolysaccharide (1 μg/mL) for 6 h. Some halo-chalcones and -azachalcones suppressed expression of pro-inflammatory factors toll-like receptor 4 (TLR4), IκB-α, transcription factor p65, interleukine 1β (IL-1β), IL-6, tumor necrosis factor α (TNF-α), and cyclooxygenase 2 (COX-2). The present results showed that the synthetic halo-azachalcones exhibited more significant inhibition than halo-chalcones. Therefore, the nitrogen atom in this series of azachalcones must play a more crucial role than the corresponding C-2 hydroxyl group of chalcones in biological activity. Our findings will lay the background for the future development of anti-inflammatory nutraceuticals.

  为了评估和比较它们的抗炎活性，我们合成了一系列 B 环、卤代查尔酮和氮杂查尔酮。小鼠 BALB/c 巨噬细胞 RAW 264.7 在脂多糖（1 μg/mL）诱导炎症 6 小时之前，用每种化合物 10 μg/mL 预处理一小时。一些卤代茶醛和氮杂茶醛抑制了促炎因子toll样受体4（TLR4）、IκB-α、转录因子p65、白细胞介素1β（IL-1β）、IL-6、肿瘤坏死因子α（TNF-α）和环氧化酶2（COX-2）的表达。本研究结果表明，合成的卤代氮杂查耳酮比卤代查耳酮具有更显著的抑制作用。因此，在生物活性方面，该系列氮杂查耳酮中的氮原子一定比相应的查耳酮 C-2 羟基发挥着更关键的作用。我们的发现将为未来抗炎保健品的开发奠定基础。
• Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships
  作者：Mauricio Cabrera、Macarena Simoens、Gabriela Falchi、M. Laura Lavaggi、Oscar E. Piro、Eduardo E. Castellano、Anabel Vidal、Amaia Azqueta、Antonio Monge、Adela López de Ceráin、Gabriel Sagrera、Gustavo Seoane、Hugo Cerecetto、Mercedes González

  DOI：10.1016/j.bmc.2007.03.031

  日期：2007.5

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.
• Anti-inflammatory, analgesic and antipyretic N-acetyl-Δ2-pyrazolines and dihydrothienocoumarines
  作者：F Manna、F Chimenti、A Bolasco、ML Cenicola、M D'Amico、C Parrillo、F Rossi、E Marmo

  DOI：10.1016/0223-5234(92)90142-n

  日期：1992.9

  1-Acetyl-3-(2-hydroxyphenyl)-5-(RR'-aryl)-4,5-dihydro-(1H)pyrazoles (2a-o) were synthesized and showed anti-inflammatory and analgesic activity. The substituents on the 5-aryl group were necessary for biological activity. R-R'-aryl-2-dihydro-1,2(4H)thieno(2,3-c)benzo(e)pyranone-4 derivatives (3a-f) also showed analgesic and anti-inflammatory activity. The position and the number of the substituents caused a modulation of analgesic or anti-inflammatory activity of the N-acetyl-DELTA2-pyrazoline 2 and dihydrothienocoumarines 3. All compounds showed low antipyretic activity.
• Chen; Yang, Taiwan Yaoxue Zazhi, 1951, vol. 3, p. 39
  作者：Chen、Yang

  DOI：——

  日期：——