3-pentyl-2,5-dihydroxy-1,4-benzoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-pentyl-2,5-dihydroxy-1,4-benzoquinone
• 英文别名: 3-amyl-2,5-dihydroxybenzoquinone-1,4；2,5-Dihydroxy-3-pentyl-1,4-benzoquinone；2,5-dihydroxy-3-pentylcyclohexa-2,5-diene-1,4-dione
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: HPGCODPPZPKVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-二羟基-1,4-苯喹酮 在 盐酸 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， -10.0~25.0 ℃ 、500.01 kPa 条件下， 反应 95.5h， 生成 3-pentyl-2,5-dihydroxy-1,4-benzoquinone
  参考文献：
  名称：

  Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)

  摘要：

  The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 mu M. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 mu M. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.045

文献信息

• Novel 3-aryl-2,5-dihydroxy-1,4-benzoquinone derivatives, their preparation method and pharmaceutical compositions containing same
  申请人：Dassonville Alexandra

  公开号：US20050085644A1

  公开（公告）日：2005-04-21

  Compound of formula (I): wherein: R 1 and R 2 , which may be identical or different, each represents hydrogen, acyl or alkyl, Ar represents aryl or heteroaryl, A represents a group selected from: R 4 represents hydrogen or alkyl, R 5 represents hydrogen, alkyl, aryl or heteroaryl, R 3 represents aryl, heteroaryl, dicyclopropylmethyl or benzhydryl, or A-R 3 represents an optionally substituted naphthyl group, with the exclusion of 2,5-dihydroxy-3-(4-methoxyphenyl)-6-(2-phenylethenyl)-1,4-benzoquinone, 2,5-dihydroxy-3-(4-methoxyphenyl)-6-(2-naphthyl)-1,4-benzoquinone and 2,5-dihydroxy-3-(2-naphthyl)-6-phenyl-1,4-benzoquinone. Medicinal products containing the same which are useful in the treatment of diseases associated with a deregulation of glycaemia.

  化合物的化学式（I）如下：其中：R1和R2，可能相同也可能不同，分别代表氢、酰基或烷基，Ar代表芳基或杂环芳基，A代表从以下选取的基团之一：R4代表氢或烷基，R5代表氢、烷基、芳基或杂环芳基，R3代表芳基、杂环芳基、二环丙基甲基或苄基，或A-R3代表一个可选择取代的萘基团，但不包括2,5-二羟基-3-(4-甲氧基苯基)-6-(2-苯乙烯基)-1,4-苯醌，2,5-二羟基-3-(4-甲氧基苯基)-6-(2-萘基)-1,4-苯醌和2,5-二羟基-3-(2-萘基)-6-苯基-1,4-苯醌。含有这种化合物的药品在治疗与血糖失调相关的疾病方面具有用途。
• NOUVEAUX DERIVES DE 3-ARYL-2,5-DIHYDROXY-1,4-BENZOQUINONES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1472208A1

  公开（公告）日：2004-11-03
• [EN] NOVEL 3-ARYL-2,5-DIHYDROXY-1,4-BENZOQUINONE DERIVATIVES, THEIR PREPARATION METHOD AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] NOUVEAUX DERIVES DE 3-ARYL-2,5-DIHYDROXY-1,4-BENZOQUINONES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SERVIER LAB

  公开号：WO2003066561A1

  公开（公告）日：2003-08-14

  Composé de Formule (I) dans laquelle : R1 et R2 identiques ou différents, représentent chacun un atome d’hydrogène ou un groupement acyle ou alkyle, Ar représente un groupement aryle ou hétéroaryle, A représente un groupement choisi parmi la Formule (II), R4 représente un atome d’hydrogène ou un groupement alkyle, R5 représente un atome d’hydrogène ou un groupement choisi parmi alkyle, aryle et hétéroaryle, R3 représente un groupement aryle, hétéroaryle, dicyclopropylméthyle ou benzhydryle, ou A-R3 représente un groupement naphtyle éventuellement substitué, à l’exclusion de la 2,5-dihydroxy-3-(4-méthoxyphényl)-6-(2-phényléthényl)-1,4-benzoquinone, de la 2,5-dihydroxy-3-(4-méthoxyphényl)-6-(2-naphtyl)-1,4-benzoquinone, et de la 2,5-dihydroxy-3-(2-naphtyl)-6-phényl-1,4-benzoquinone.
• Design, synthesis, and SAR of embelin analogues as the inhibitors of PAI-1 (plasminogen activator inhibitor-1)
  作者：Fanglei Chen、Guiping Zhang、Zebin Hong、Zhonghui Lin、Min Lei、Mingdong Huang、Lihong Hu

  DOI：10.1016/j.bmcl.2014.03.045

  日期：2014.5

  The natural product embelin was found to have PAI-1 inhibitory activity with the IC50 value of 4.94 mu M. Based on the structure of embelin, a series of analogues were designed, synthesized, and evaluated for their ability to inhibit PAI-1. The SAR study on these compounds disclosed that the inhibitory potency largely depended on the hydroxyl groups at C2 and C5, and the length of the alkyl chains at C3 and C6. Compound 11 displayed the best PAI-1 inhibitory potency with the IC50 value of 0.18 mu M. (C) 2014 Elsevier Ltd. All rights reserved.