2,2-dimethyl-5-<4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy>pentanoic acid | 179337-50-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2-dimethyl-5-<4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy>pentanoic acid
• 英文别名: 2,2-Dimethyl-5-[4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy] pentanoic acid；5-[4-Hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid
• CAS: 179337-50-9
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: CHIDSVAEEUZBND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-<4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy>pentanoic acid 在 2,2'-二硫二吡啶 、 silver perchlorate 、 三苯基膦 作用下， 以 乙腈 、 xylene 为溶剂， 反应 12.0h， 以46%的产率得到9-ethyl-14-hydroxy-6,6,13,15,16-pentamethyl-2,8-dioxabicyclo[10.4.0]hexadec-12,14,16-trien-7-one
  参考文献：
  名称：

  Medium sized lactones with hypolipidaemic and antioxidant activity: synthesis and biological evaluation of promising dual-action anti-atherosclerosis drugs

  摘要：

  Macrocyclic lactones 1a-b have been synthesized and their potential therapeutic value evaluated. The key structural feature of these active 'chimera' compounds is the 12-membered lactone ring that brings together the well-known polysubstituted hydroquinone moiety of antioxidants and the alpha,alpha-dimethyl substituted acyl residue of gemfibrozil. Lactones 1a-b showed better activity than probucol, a classical phenolic antioxidant, in preventing the Cu+ (+)-induced oxidative modification of human LDL. The hypolipidaemic activity of the new lactones, evaluated as the inhibition of lipids biosynthesis in Hep-G(2) cells, was comparable to that of gemfibrozil. These features, added to the lack of cytotoxicity, make this new class of medium sized lactones promising dual-action drugs useful as anti-atherosclerosis agents. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00252-1
• 作为产物：
  描述：

  5-<4-acetoxy-2-(3-oxopentyl)-3,5,6-trimethylphenoxy>-2,2-dimethylpentanoic acid isopropyl ester 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 19.0h， 生成 2,2-dimethyl-5-<4-hydroxy-2-(3-hydroxypentyl)-3,5,6-trimethylphenoxy>pentanoic acid
  参考文献：
  名称：

  Medium sized lactones with hypolipidaemic and antioxidant activity: synthesis and biological evaluation of promising dual-action anti-atherosclerosis drugs

  摘要：

  Macrocyclic lactones 1a-b have been synthesized and their potential therapeutic value evaluated. The key structural feature of these active 'chimera' compounds is the 12-membered lactone ring that brings together the well-known polysubstituted hydroquinone moiety of antioxidants and the alpha,alpha-dimethyl substituted acyl residue of gemfibrozil. Lactones 1a-b showed better activity than probucol, a classical phenolic antioxidant, in preventing the Cu+ (+)-induced oxidative modification of human LDL. The hypolipidaemic activity of the new lactones, evaluated as the inhibition of lipids biosynthesis in Hep-G(2) cells, was comparable to that of gemfibrozil. These features, added to the lack of cytotoxicity, make this new class of medium sized lactones promising dual-action drugs useful as anti-atherosclerosis agents. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00252-1

文献信息

• Lactones with antioxidising and hypolipidaemic activity useful in the
  申请人：Alfa Wassermann S.p.A.

  公开号：US05608084A1

  公开（公告）日：1997-03-04

  Lactones of formula ##STR1## and their pharmacologically acceptable salts endowed with antioxiding and hypolipidaemic properties and that show the capability to prevent and/or to delay the oxidative modification of the lipoproteins by competing with the chain of propagation of the lipidic peroxidation by means of an effective scavenging of the peroxylic radicals. The compounds object of the present invention are useful in the treatment of the atherosclerosis and of many correlated vascular pathologies, like ischaemic cardiopathies (angina pectoris and myocardial infarction), cerebral thrombosis and peripheral arteriopathies, because the high plasma levels of lipids and the oxidative modifications of the low density lipoproteins (LDL) represent crucial events in the pathogenesis of the atherosclerosis.

  化学式为##STR1##的内酯及其具有抗氧化和降脂作用的药用可接受盐，具有防止和/或延迟脂质过氧化的能力，通过有效清除过氧自由基与脂质过氧化的传播链竞争。本发明的化合物可用于治疗动脉粥样硬化及许多相关的血管病理，如缺血性心脏病（心绞痛和心肌梗塞）、脑血栓形成和外周动脉病变，因为高血浆脂质水平和低密度脂蛋白（LDL）的氧化修饰在动脉粥样硬化的发病机制中起着关键作用。
• Lactones with antioxidising and hypolipidaemic activity useful in the therapy of the atherosclerosis
  申请人：ALFA WASSERMANN S.p.A.

  公开号：EP0718295B1

  公开（公告）日：1998-04-22
• US5608084A
  申请人：——

  公开号：US5608084A

  公开（公告）日：1997-03-04
• Medium sized lactones with hypolipidaemic and antioxidant activity: synthesis and biological evaluation of promising dual-action anti-atherosclerosis drugs
  作者：Claudia Baldazzi、Francesca Calderoni、Emanuela Marotta、Silvano Piani、Paolo Righi、Goffredo Rosini、Stefano Saguatti、Roberta Tiozzo、Sebastiano Calandra、Francesca Venturelli

  DOI：10.1016/s0968-0896(98)00252-1

  日期：1999.2

  Macrocyclic lactones 1a-b have been synthesized and their potential therapeutic value evaluated. The key structural feature of these active 'chimera' compounds is the 12-membered lactone ring that brings together the well-known polysubstituted hydroquinone moiety of antioxidants and the alpha,alpha-dimethyl substituted acyl residue of gemfibrozil. Lactones 1a-b showed better activity than probucol, a classical phenolic antioxidant, in preventing the Cu+ (+)-induced oxidative modification of human LDL. The hypolipidaemic activity of the new lactones, evaluated as the inhibition of lipids biosynthesis in Hep-G(2) cells, was comparable to that of gemfibrozil. These features, added to the lack of cytotoxicity, make this new class of medium sized lactones promising dual-action drugs useful as anti-atherosclerosis agents. (C) 1999 Elsevier Science Ltd. All rights reserved.