(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hexoxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene | 1220450-01-0

• 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,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hexoxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene
• CAS: 1220450-01-0
• 化学式: C₄₉H₅₀O₆
• 分子量: 734.932
• InChiKey: FDZVLGAAILYUQO-NXWRKTHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hexoxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene 在 10% palladium on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (2R,3S)-2-(3,4-dihydroxyphenyl)-3-hexoxy-3,4-dihydro-2H-chromene-5,7-diol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism

  摘要：

  We report here the synthesis and biological properties of 3-O-alkyl analogues of(+)-catechin (5), which itself is one of the major natural polyphenols found in green tea and has several physiological activities. Starting from 5, a series of 3-O-alkyl-(+)-catechin derivatives were investigated as potent antimicrobial agents. The presence of an alkyl chain rather than acyl on 3-O- showed an increase in antimicrobial activity which may be due to stability in standard culture condition. The most promising compound is 8e, 3-O-decyl analogue, with the MIC of 0.5-2,32-128 and 2-4 mu g/mL against Gram-positive bacteria, Gram-negative bacteria and human pathogenic fungi, respectively. Regarding action mechanism, the antimicrobial activity is possibly due to the lipophilicity and disrupting ability of the analogues to the liposome membrane. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.11.045
• 作为产物：
  描述：

  1-碘己烷 、 (2R,3S)-5,7-二(苄氧基)-2-[3,4-二(苄氧基)苯基]-3-色满醇 在 cesium hydroxide 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-hexoxy-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromene
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism

  摘要：

  We report here the synthesis and biological properties of 3-O-alkyl analogues of(+)-catechin (5), which itself is one of the major natural polyphenols found in green tea and has several physiological activities. Starting from 5, a series of 3-O-alkyl-(+)-catechin derivatives were investigated as potent antimicrobial agents. The presence of an alkyl chain rather than acyl on 3-O- showed an increase in antimicrobial activity which may be due to stability in standard culture condition. The most promising compound is 8e, 3-O-decyl analogue, with the MIC of 0.5-2,32-128 and 2-4 mu g/mL against Gram-positive bacteria, Gram-negative bacteria and human pathogenic fungi, respectively. Regarding action mechanism, the antimicrobial activity is possibly due to the lipophilicity and disrupting ability of the analogues to the liposome membrane. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2009.11.045

文献信息

• Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism
  作者：Ki Duk Park、Sung Jin Cho

  DOI：10.1016/j.ejmech.2009.11.045

  日期：2010.3

  We report here the synthesis and biological properties of 3-O-alkyl analogues of(+)-catechin (5), which itself is one of the major natural polyphenols found in green tea and has several physiological activities. Starting from 5, a series of 3-O-alkyl-(+)-catechin derivatives were investigated as potent antimicrobial agents. The presence of an alkyl chain rather than acyl on 3-O- showed an increase in antimicrobial activity which may be due to stability in standard culture condition. The most promising compound is 8e, 3-O-decyl analogue, with the MIC of 0.5-2,32-128 and 2-4 mu g/mL against Gram-positive bacteria, Gram-negative bacteria and human pathogenic fungi, respectively. Regarding action mechanism, the antimicrobial activity is possibly due to the lipophilicity and disrupting ability of the analogues to the liposome membrane. Published by Elsevier Masson SAS.