[(2R,3R)-5,7-bis(phenylmethoxy)-2-(3-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate | 863237-61-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: [(2R,3R)-5,7-bis(phenylmethoxy)-2-(3-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 863237-61-0
• 化学式: C₆₄H₅₄O₉
• 分子量: 967.127
• InChiKey: OBWGNBFITOVCKV-VOVXCRLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.06
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  90.91
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R)-5,7-bis(phenylmethoxy)-2-(3-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 [(2R,3R)-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
  参考文献：
  名称：

  Structure–activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors

  摘要：

  The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introduction of a hydrophobic benzyl group into the 8 position of A ring did not significantly affect the proteasome-inhibitory potency. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.056
• 作为产物：
  描述：

  (1R,2R)-1-(3'-benzyloxyphenyl)-3-(2''-hydroxy-4'',6''-dibenzyloxyphenyl)propane-1,2-diol 在 草酰氯 、 乙酰溴 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.08h， 生成 [(2R,3R)-5,7-bis(phenylmethoxy)-2-(3-phenylmethoxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris(phenylmethoxy)benzoate
  参考文献：
  名称：

  Structure–activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors

  摘要：

  The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introduction of a hydrophobic benzyl group into the 8 position of A ring did not significantly affect the proteasome-inhibitory potency. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.056

文献信息

• Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus
  作者：James C. Anderson、Catherine Headley、Paul D. Stapleton、Peter W. Taylor

  DOI：10.1016/j.tet.2005.05.086

  日期：2005.8

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.