2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-(1-pentyl) benzoic acid | 80489-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-(1-pentyl) benzoic acid
• 英文别名: amorfrutin 2；NP-003521；2-hydroxy-4-methoxy-3-(3-methyl-2-butenyl)-6-pentyl-benzoic acid；2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-pentylbenzoic acid
• CAS: 80489-91-4
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: UJSSSFNGQWZNEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-(1-pentyl) benzoic acid 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 生成 5-Methoxy-2,2-dimethyl-7-pentyl-chroman
  参考文献：
  名称：

  来自棘果甘草的异戊二烯化间苯二酚衍生物

  摘要：

  摘要 甘草叶和末端枝条的醚提取物提供了四种新的异戊二烯化间苯二酚衍生物。其中两种是大麻酚和大麻酚酸的异戊二烯异戊二烯。

  DOI：

  10.1016/0031-9422(81)84044-7
• 作为产物：
  描述：

  2-Hydroxy-4-methoxy-3-(3-methyl-but-2-enyl)-6-pentyl-benzoic acid methyl ester 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 2-hydroxy-4-methoxy-3-(3-methylbut-2-enyl)-6-(1-pentyl) benzoic acid
  参考文献：
  名称：

  Structural Characterization of Amorfrutins Bound to the Peroxisome Proliferator-Activated Receptor γ

  摘要：

  Amorfrutins are a family of natural products with high affinity to the peroxisome proliferator-activated receptor gamma (PPAR gamma), a nuclear receptor regulating lipid and glucose metabolism. The PPAR gamma agonist rosiglitazone increases insulin sensitivity and is effective against type II diabetes but has severe adverse effects including weight gain. Amorfrutins improve insulin sensitivity and dyslipidemia but do not enhance undesired fat storage. They bear potential as therapeutics or prophylactic dietary supplements. We identified amorfrutin B as a novel partial agonist of PPAR gamma with a considerably higher affinity than that of previously reported amorfrutins, similar to that of rosiglitazone. Crystal structures reveal the geranyl side chain of amorfrutin B as the cause of its particularly high affinity. Typical for partial agonists, amorfrutins 1, 2, and B bind helix H3 and the beta-sheet of PPARy gamma but not helix H12.

  DOI：

  10.1021/jm3013272

文献信息

• [EN] AMORFRUTIN ANALOGS AS PPARGAMMA-MODULATORS<br/>[FR] ANALOGUES DE L'AMORFRUTINE EN TANT QUE MODULATEURS DE PPARGAMMA
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2014177593A1

  公开（公告）日：2014-11-06

  The present invention relates to Amorfrutin analogues and stereoisomeric forms, solvates, hydrates, conjugates and/or pharmaceutically acceptable salts of these compounds as well as pharmaceutical compositions containing at least one of these Amorfrutin analogues together with pharmaceutically acceptable carrier, excipient and/or diluents. Said Amorfrutin analogues have been identified as modulators of the peroxisome proliferator-activated receptors (PPARs), especially PPARϒ and are useful for the prevention and treatment of metabolic diseases, inflammatory diseases, cancer and preparation of phytomedicals and/or functional food products for prevention of metabolic diseases.

  本发明涉及Amorfrutin类似物和立体异构体形式，以及这些化合物的溶剂结晶体、水合物、结合物和/或药用可接受的盐，以及包含至少一种这些Amorfrutin类似物的药物组合物，与药用可接受的载体、赋形剂和/或稀释剂。所述的Amorfrutin类似物已被确定为过氧化物酶增殖物活化受体（PPARs）的调节剂，特别是PPARϒ，并且对于预防和治疗代谢性疾病、炎症性疾病、癌症以及制备植物药和/或功能性食品产品以预防代谢性疾病是有用的。
• NOVEL NUTRACEUTICAL AND PHARMACEUTICAL COMPOSITIONS AND USE THEREOF FOR THE TREATMENT, CO-TREATMENT OR PREVENTION OF INFLAMMATORY DISORDERS
  申请人：DSM IP Assets B.V.

  公开号：EP1984317A1

  公开（公告）日：2008-10-29
• Novel Nutraceutical and Pharmaceutical Compositions and Use Thereof for the Treatment, Co-Treatment or Prevention of Inflammatory Disorders
  申请人：Raederstorff Daniel

  公开号：US20080319071A1

  公开（公告）日：2008-12-25

  The present invention relates to new methoxylated aromatic compounds. It also relates to novel compositions comprising methoxylated aromatic compounds as well as to the use of these compositions as a medicament, in particular as a medicament for the treatment, co-treatment or prevention of inflammatory disorders.
• NOVEL COMPOSITIONS
  申请人：Raederstorff Daniel

  公开号：US20100055218A1

  公开（公告）日：2010-03-04

  The present invention relates to novel compositions comprising rosehip and at least one additional component e.g. selected from ligustilide, oleuropein (I), oleuropein aglycone (II), hydroxytyrosol, genistein, magnolol, honokiol, magnolia bark extract, cashew fruit extract and Glycyrrhiza foetida as well as to the use of these compositions as a medicament, in particular as a medicament for the treatment, co-treatment or prevention of inflammatory disorders.
• MYCOBACTERIUM MEMBRANE PROTEASE AS A TARGET FOR INHIBITORS OF INTRABACTERIAL pH HOMEOSTASIS
  申请人：Nathan Carl

  公开号：US20110190234A1

  公开（公告）日：2011-08-04

  The present invention is directed to methods and compounds for inhibiting bacterial growth and treating a bacterial infection in a subject. These methods involve providing an inhibitor of intrabacterial pH homeostasis, including inhibitors of the Mycobacterium tuberculosis Rv3671c gene encoded membrane protease. Methods for identifying novel compounds that disrupt intrabacterial pH homeostasis and their use for inhibiting bacterial growth and treating a bacterial infection in a subject are also disclosed.