(-)-ECG-7TBS | 853687-37-3

• 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: (-)-ECG-7TBS
• 英文别名: [(2R,3R)-2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3,4-dihydro-2H-chromen-3-yl] 3,4,5-tris[[tert-butyl(dimethyl)silyl]oxy]benzoate
• CAS: 853687-37-3
• 化学式: C₆₄H₁₁₆O₁₀Si₇
• 分子量: 1242.22
• InChiKey: XJXFNLNHCOJHCQ-MSDPODROSA-N

物化性质

• 沸点：
  866.5±65.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.28
• 重原子数：
  81
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (-)-ECG-7TBS 在 sodium chlorite 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.5h， 生成 3,4,5-tris((tert-butyldimethylsilyl)oxy)benzoic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of hydrolytically stable (−)-epicatechin gallate analogues for the modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Hydrolytically more stable analogues of (-)-epicatechin gallate (ECg) have been synthesised from ECg where an amine or amide function has been substituted for the ester linkage that joins the C-ring with the galloyl D-ring. Sub-inhibitory concentrations (25 mg/L) of the amide analogue 7, possessing the natural C-3 stereochemistry, were able to reduce the resistance to oxacillin of three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) comparable to levels achieved with ECg. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.063
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (-)-表儿茶素没食子酸酯 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到(-)-ECG-7TBS
  参考文献：
  名称：

  [EN] PYRANS FOR USE IN THE TREATMENT OF INFECTION
  [FR] PYRANES DESTINES A ETRE UTILISES DANS LE TRAITEMENT DE L'INFECTION

  摘要：

  提供一种新化合物，其通式为(I)，其中每个R为氢，芳基，C1-6烷基，三烷基硅基或酰基，每个R1从羟基，C1-6烷氧基和酰氧基中选择；每个R2为H，C1-4烷基，三烷基硅基或酰基；R3为H或Me；n为0至5之间的任何烷基基团，包括可能被芳基，C1-4烷基，C1-4烷氧基，羟基，三烷基硅氧基或酰氧基取代的烷基基团。该化合物是表现为表儿茶素没食子酸或表儿茶素没食子酸的类似物，具有天然酯键的酰胺键位，对酯酶酶的水解具有抗性。这些化合物可用于调节各种感染对β-内酰胺类抗生素的耐药性，特别是耐甲氧西林金黄色葡萄球菌（MRSA）。描述了含有这种新化合物的药物组合和这些新化合物与β-内酰胺类抗生素的组合。

  公开号：

  WO2006003458A1

文献信息

• [EN] PYRANS FOR USE IN THE TREATMENT OF INFECTION<br/>[FR] PYRANES DESTINES A ETRE UTILISES DANS LE TRAITEMENT DE L'INFECTION
  申请人：UNIV LONDON PHARMACY

  公开号：WO2006003458A1

  公开（公告）日：2006-01-12

  There is provided a novel compound of the general formula (I), in which each R is hydrogen, aryl, C1-6 alkyl, trialkylsilyl, or acyl, each R1 is selected from hydroxy, C1-6 alkoxy and acyloxy; each R2 is H, C1-4 alkyl, trialkylsilyl or acyl; R3 is H or Me; and n is 0 to 5 any of the alkyl groups including alkyl groups in alkoxy, acyl and acyloxy groups which may be substituted by aryl, C1-4 alkyl, C1-4 alkoxy, hydroxyl, trialkylsiloxy or acyloxy groups. The compound is an analogue of epigalcatechin galate or epicatechin galate, with an amide bonding placed of the natural ester bond, with resistance to hydrolysis by esterase enzymes. The compounds may be used to modulate the resistance to β-lactam antibiotics of various infections, especially methicillin resistant staphylococcus aureus (MRSA). Pharmaceutical compositions containing the novel compounds and combinations of the novel compounds and β-lactam antibiotics are described.

  提供一种新化合物，其通式为(I)，其中每个R为氢，芳基，C1-6烷基，三烷基硅基或酰基，每个R1从羟基，C1-6烷氧基和酰氧基中选择；每个R2为H，C1-4烷基，三烷基硅基或酰基；R3为H或Me；n为0至5之间的任何烷基基团，包括可能被芳基，C1-4烷基，C1-4烷氧基，羟基，三烷基硅氧基或酰氧基取代的烷基基团。该化合物是表现为表儿茶素没食子酸或表儿茶素没食子酸的类似物，具有天然酯键的酰胺键位，对酯酶酶的水解具有抗性。这些化合物可用于调节各种感染对β-内酰胺类抗生素的耐药性，特别是耐甲氧西林金黄色葡萄球菌（MRSA）。描述了含有这种新化合物的药物组合和这些新化合物与β-内酰胺类抗生素的组合。
• Synthesis and antibacterial activity of hydrolytically stable (−)-epicatechin gallate analogues for the 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.bmcl.2005.03.063

  日期：2005.5

  Hydrolytically more stable analogues of (-)-epicatechin gallate (ECg) have been synthesised from ECg where an amine or amide function has been substituted for the ester linkage that joins the C-ring with the galloyl D-ring. Sub-inhibitory concentrations (25 mg/L) of the amide analogue 7, possessing the natural C-3 stereochemistry, were able to reduce the resistance to oxacillin of three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) comparable to levels achieved with ECg. (c) 2005 Elsevier Ltd. All rights reserved.