2',4-dihydroxy-6'-benzyloxychalcone | 86788-63-8

• 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: 2',4-dihydroxy-6'-benzyloxychalcone
• 英文别名: 6'-benzyloxy-4,2'-dihydroxychalcone；(E)-1-(2-(benzyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one；(E)-3-(4-hydroxyphenyl)-1-(2-hydroxy-6-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 86788-63-8；105285-10-7
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: LTDUVNSCZUJEBU-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',4-dihydroxy-6'-benzyloxychalcone 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢气 、 双氧水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 10.58h， 生成
  参考文献：
  名称：

  Patil, A. D.; Deshpande, V. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, p. 109 - 113

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 36.0h， 生成 2',4-dihydroxy-6'-benzyloxychalcone
  参考文献：
  名称：

  Patil, A. D.; Deshpande, V. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, p. 109 - 113

  摘要：

  DOI：

文献信息

• Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells
  作者：Eeda Venkateswararao、Vinay K. Sharma、Jieun Yun、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmc.2014.04.045

  日期：2014.7

  To investigate the anti-proliferative effect of NF-kappa B inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NE-kappa B inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-kappa B inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-kappa B inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NE-kappa B inhibition and anti-proliferative activity though the extent is not directly proportional to each other. (C) 2014 Elsevier Ltd. All rights reserved.
• Takahashi, Hiroshi; Kubota, Yumiko; Fang, Lin, Heterocycles, 1986, vol. 24, # 4, p. 1099 - 1107
  作者：Takahashi, Hiroshi、Kubota, Yumiko、Fang, Lin、Onda, Masayuki

  DOI：——

  日期：——
• Structural requirement of chalcones for the inhibitory activity of interleukin-5
  作者：Hyun-Mo Yang、Hye-Rim Shin、Soo-Hyun Cho、Seong-Cheol Bang、Gyu-Yong Song、Jung-Hun Ju、Mi-Kyeong Kim、Seung-Ho Lee、Jae-Chun Ryu、Youngsoo Kim

  DOI：10.1016/j.bmc.2006.10.007

  日期：2007.1.1

  Novel chalcones were found as potent inhibitors of interleukin (IL)-5. 1-(2-Benzyloxy-6-hydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one (2b, 78.8% inhibition at 50 mu M, IC50 = 25.3 mu M) was initially identified as a potent inhibitor of IL-5. This shows the compatible activity with budesonide or sophoricoside. To identify structural requirements, 26 chalcones were prepared and their inhibitory activities were tested against IL-5. Among them, compound 4-[(E)-3-(2-cyclohexylmethoxy-6-hydroxyphenyl)-3-oxoprop-1-enyl]benzenesulfonamide (2w, 99.5% inhibition at 50 mu M, IC50 = 1-8 mu M) shows the most potent activity. The important structural requirements of these chalcone analogs exhibiting the inhibitory activity against IL-5 were recognized as the following. (1) The hydrophobic group such as benzyloxy or cyclohexylmethoxy at 6-position of A ring is necessary. (2) The existence of phenolic hydroxyl at 6-position of A ring is critical. (3) Propenone unit as alpha,beta-unsaturated ketone is essential. (4) Electron withdrawing groups with hydrogen acceptor property at 4-position of B ring enhance the activity and quantitative structure-activity relationship of 2 regarding these substituents was determined. (c) 2006 Elsevier Ltd. All rights reserved.
• TAKAHASHI HIROSHI; KUBOTA YUMIKO; LIN FANG; ONDA MASAYUKI, HETEROCYCLES, 24,(1986) N 3, 1099-1107
  作者：TAKAHASHI HIROSHI、 KUBOTA YUMIKO、 LIN FANG、 ONDA MASAYUKI

  DOI：——

  日期：——
• A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB
  作者：Eeda Venkateswararao、Vinay K. Sharma、Ki-Cheul Lee、Niti Sharma、Sun-Hong Park、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2012.05.019

  日期：2012.8

  To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-kappa B activation (IC50 = 10 mu M), a series of its analogues was prepared and studied for their in vitro activities against LPS induced NF-kappa B inhibition in RAW 264.7 cells. Among the synthesized derivatives, (E)-1-(2-(decyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1050 = 2.7 mu M) and (E)-1-(2-hydroxy-6-(tetradecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC50 = 4.2 mu M) showed the most potent inhibition. The SAR studies confirmed that the length (C-8-C-14) and C-6 position of linear alkyl chain of ring A is an important factor for the inhibitory activity. Hydroxyl group and its location at 4-position on ring B is also important for the inhibition. The alpha,beta-unsaturated ketone moiety appears as a crucial motif of chalcones for the activity. (C) 2012 Elsevier Masson SAS. All rights reserved.