(E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one | 84002-48-2

• 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)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-benzyloxy-2-hydroxyphenyl)-3-(4-benzyloxyphenyl)propenone；1-(4-benzyloxy-2-hydroxyphenyl)-3-(4-benzyloxyphenyl)propenone；1-(4-benzoxy-2-hydroxyphenyl)-3-(4-benzoxyphenyl)propenone；4,4'-bis(benzyloxy)-2'-hydroxychalcone；4,4'-dibenzyloxy-2'-hydroxychalcone；2'-hydroxy-4.4'-dibenzyloxy-trans-chalcone；2'-Hydroxy-4,4'-bis(benzyloxy)chalcone；(E)-1-(2-hydroxy-4-phenylmethoxyphenyl)-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 84002-48-2
• 化学式: C₂₉H₂₄O₄
• 分子量: 436.507
• InChiKey: OXJNAMHGUAYTFA-QGOAFFKASA-N

物化性质

• 熔点：
  134-136 °C(Solv: ethanol (64-17-5))
• 沸点：
  662.4±55.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 生成 4',7-di-O-benzyl-5-deoxykaempferol
  参考文献：
  名称：

  RSK特异性抑制剂SL0101的活性的结构基础。

  摘要：

  p90核糖体S6激酶（RSK）的不适当活性已与各种人类癌症以及其他病理相关。我们先前报道了称为SL0101的天然产物山奈酚3-O-（3''，4''-二-O-乙酰基-α-1-鼠李糖吡喃糖苷）的分离，表征和合成。CE，Poteet-Smith；徐Y TM Errington; Hecht，SM；Lannigan，DA Cancer Res。，2005，65，1027-1034：Xu，Y.-M。JA，史密斯；达兰·兰尼根（Lannigan）；Hecht，SM Bioorg。中 Chem。，2006，14，3974-3977：Maloney，DJ。Hecht，SM组织。Lett。，2005，7，1097-1099]。SL0101是一种有效且特异性的RSK抑制剂。因此，我们对这种先导化合物的抑制活性进行了结构基础分析。在体外激酶测定中，我们发现鼠李糖部分和4'，5的酰化作用 7-羟基负责维持RSK与

  DOI：

  10.1016/j.bmc.2007.03.087
• 作为产物：
  描述：

  2-羟基-1-(4-羟基苯基)乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(4-(benzyloxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  An Efficient Total Synthesis of Resokaempferol 3-O-β-D-Glucoside

  摘要：

  通过使用 NaH 的高效糖基化方法，以 2,4-二羟基苯乙酮为原料，分六步合成了人工黄酮醇苷 Resokaempferol 3-O-β-d-glucoside，总产率为 40%。

  DOI：

  10.1246/cl.2011.1135

文献信息

• Enantioselective Synthesis of Flavan-3-ols Using a Mitsunobu Cyclization
  作者：Karsten Krohn、Ishtiaq Ahmed、Markus John

  DOI：10.1055/s-0028-1083361

  日期：——

  The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC.

  通过从相应的二醇进行一步Mitsunobu反应，以高立体选择性和区位选择性成功合成了四种具有不同取代模式和电子密度的黄酮-3-醇，这些二醇是通过对合适的烯烃进行手性选择性的Sharpless二羟基化制备的。在Mitsunobu环化过程中，六元环的黄酮-3-醇是唯一的环化产物，理论上可能形成的五元环并未被观察到。这些黄酮醇是合成二聚体（如原花青素）或其他偶联产物（如强效DNA聚合酶β抑制剂myristinin A中的黄酮部分）的重要起始材料。Sharpless二羟基化和Mitsunobu环化步骤的对映选择性通过手性高效液相色谱法进行了监测。
• Mahal et al., Journal of the Chemical Society, 1935, p. 866
  作者：Mahal et al.

  DOI：——

  日期：——
• Iinuma, Munekazu; Matsuura, Shin; Tanaka, Toshiyuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1472 - 1476
  作者：Iinuma, Munekazu、Matsuura, Shin、Tanaka, Toshiyuki

  DOI：——

  日期：——
• 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.
• 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
  作者：Nadine De Meyer、Achiel Haemers、Lallan Mishra、Hrishi Kesh Pandey、L. A. C. Pieters、Dirk A. Vanden Berghe、Arnold J. Vlietinck

  DOI：10.1021/jm00106a039

  日期：1991.2

  4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5-mu-g/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.