3-Dodecyl-cianidanol | 71628-08-5

• 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: 3-Dodecyl-cianidanol
• 英文别名: 3-O-dodecyl catechin；2H-1-Benzopyran-5,7-diol, 2-(3,4-dihydroxyphenyl)-3-(dodecyloxy)-3,4-dihydro-, (2R-trans)-；(2R,3S)-2-(3,4-dihydroxyphenyl)-3-dodecoxy-3,4-dihydro-2H-chromene-5,7-diol
• CAS: 71628-08-5
• 化学式: C₂₇H₃₈O₆
• 分子量: 458.595
• InChiKey: VILVUXGYJZIYEI-RRPNLBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3-dodecoxy-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 3-Dodecyl-cianidanol
  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

• [EN] AGENT FOR PREVENTING AND TREATING INFECTIOUS DISEASE BY INFLUENZA VIRUS COMPRISING CATHECHIN DERIVATIVE COMPOUNDS<br/>[FR] AGENT DESTINÉ À LA PRÉVENTION ET AU TRAITEMENT DE L'INFECTION PAR LE VIRUS DE L'INFLUENZA, COMPRENANT DES COMPOSÉS DÉRIVÉS DE LA CATHÉCHINE
  申请人：PROTHEON CO LTD

  公开号：WO2007139350A1

  公开（公告）日：2007-12-06

  [EN] The present invention relates to a preventive and therapeutic agent for infectious disease by influenza virus comprising catechin derivative compounds as an effective ingredient, more precisely a preventive and therapeutic agent for infectious disease by influenza virus comprising catechin derivative compounds as an effective ingredient which can inhibit the growth of influenza virus and the interaction between influenza virus and cells. The preventive and therapeutic agent of the present invention not only has the effect described above but also plays a role in the interaction between various subtypes of influenza virus and cells, so that this agent can be effectively used for the prevention and treatment of infectious disease by human influenza virus and avian influenza virus as well.
  [FR] L'invention porte sur un agent destiné à la prévention et au traitement de l'infection par le virus de l'influenza, qui comprend comme principe actif des composés dérivés de la cathéchine, et en particulier sur un agent destiné à la prévention et au traitement de l'infection par le virus de l'influenza qui comprend des composés dérivés de la cathéchine comme principe actif permettant d'inhiber la croissance du virus de l'influenza et l'interaction entre le virus de l'influenza et les cellules. L'agent de prévention et de traitement de l'invention non seulement possède l'effet précité, mais joue également un rôle dans l'interaction entre divers sous-types de virus de l'influenza et cellules, de sorte qu'on peut l'utiliser avec efficacité pour la prévention et le traitement d'une infection par le virus de l'influenza humain et aviaire.
• 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.