4-hydroxy-3,5-di-tert-butylphenylmercaptoacetic acid | 61151-53-9

• 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: 4-hydroxy-3,5-di-tert-butylphenylmercaptoacetic acid
• 英文别名: (3,5-di-tert-butyl-4-hydroxyphenylthio)acetic acid；2,6-di-tert-butyl-4-(carboxymethylthio)phenol；4-carboxymethylthio-2,6-di-tert-butylphenol；2-<(3,5-Di-t-butyl-4-hydroxyphenyl)thio>ethansaeure；2-[(3,5-Di-t-butyl-4-hydroxyphenyl)thio]ethansaeure；Acetic acid, [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-；2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylacetic acid
• CAS: 61151-53-9
• 化学式: C₁₆H₂₄O₃S
• 分子量: 296.431
• InChiKey: JQTKPQMBPABUJG-UHFFFAOYSA-N

物化性质

• 沸点：
  392.2±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3,5-di-tert-butylphenylmercaptoacetic acid 在 copper diacetate 作用下， 以 异丙醇 为溶剂， 反应 0.67h， 生成 3,3',5,5'-四叔丁基-4,4'-联苯醌
  参考文献：
  名称：

  Medzhidov, A. A.; Farzaliev, V. M.; Kasumov, V. T., Journal of general chemistry of the USSR, 1982, vol. 52, # 1, p. 93 - 96

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二叔丁基-4-巯基苯酚 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxy-3,5-di-tert-butylphenylmercaptoacetic acid
  参考文献：
  名称：

  Dual Inhibition of Human Leukocyte Elastase and Lipid Peroxidation:  In Vitro and in Vivo Activities of Azabicyclo[2.2.2]octane and Perhydroindole Derivatives

  摘要：

  A series of potent and selective human leukocyte elastase (HLE) inhibitors of the Val-Pro-Val type has been developed. Initially, the central proline residue was replaced by nonnatural amino acids Phi ((2S,3aS,7aS)-perhydroindole-2-carboxy acid) and Abo ((3S)-2-azabicyclo[2.2.2]octane-3-carboxylic acid), and secondly several groups able to confer antioxidant properties to the molecule were introduced at the lipophilic N-terminal side chain. When compared to reference inhibitors, in vitro HLE inhibitory potency was maintained (10-100 nM) both with compounds containing the antioxidant moiety at the end of the N-terminal side chain and with compounds in which the N-terminal valine of the tripeptidic sequence had been replaced by a epsilon-substituted lysine. The lipidic peroxidation inhibitory potency of this series of inhibitors was found to be similar to that of the reference antioxidant compounds (around 1 mu M). Moreover, HLE-induced hemorrhage in the hamster lung was effectively prevented (40-60% at 15 mu g/ kg) by most of the inhibitors tested when administered intratracheally 3 h before instillation of elastase. Among the most active analogs, compounds 11a,c,g were still active when administered 18 h before elastase. Interestingly, compound 14a was able to prevent HLE-mediated lung damage when administered 72 h prior to enzymatic challenge, indicating exceptional stability and retention in the lung. Finally, in a 14-day chronic model of emphysema in the hamster, 14a significantly conserved alveolar spaces, a marker of lung tissue destruction, send was more potent; than reference inhibitor ICI 200 880. This indicates that addition of peroxidation inhibitory properties to an HLE inhibitor can provide a powerful in vivo inhibitor of pulmonary tissue destruction.

  DOI：

  10.1021/jm960772z

文献信息

• Hypolipidemic arylthioalkanoic acids
  作者：Eugene R. Wagner、Robert G. Dull、Larry G. Mueller、Bobbie J. Allen、Alfred A. Renzi、Darrel J. Rytter、James W. Barnhart、Carol Byers

  DOI：10.1021/jm00218a004

  日期：1977.8

  A series of arylthioalkanoic acids related to probucol was studied for hypolipidemic activity. Homologation of the alkyl side chain led to marked changes in the serum cholesterol and serum triglyceride lowering activity in rats with the best combination of properties appearing in compound 7, 2-[3,5-di-tert-butyl-4-hydroxyphenyl)thio]hexanoic acid. Modification of the ring substitution failed to improve

  研究了与普罗布考有关的一系列芳硫基链烷酸的降血脂活性。烷基侧链的同源性导致大鼠血清胆固醇和血清甘油三酯降低活性的明显变化，其中化合物7、2- [3,5-二叔丁基-4-羟基苯基）硫基化合物具有最佳的特性组合己酸。尽管经验观察到亲脂取代是必要的，但是环取代的修饰不能提高活性。除去酚羟基可制得性质类似于7但活性稍低的化合物23。用氧气代替硫增加了该系列的毒性。外消旋体7的拆分并没有改变该化合物的活性。
• New derivatives of amidines, their preparation, their use as medicaments and the pharmaceutical compositions containing them
  申请人：Auvin Serge

  公开号：US20050261269A1

  公开（公告）日：2005-11-24

  Novel derivatives of amidines of formula wherein the substituents are defined as in the specification which are useful for inhibiting activity on NO-synthase enzymes producing nitrogen mono oxide and/or trapping the reactive oxygen species (ROS) making them useful for treating various diseases.

  该项发明涉及公式中所定义的取代基的新型氨基甲酸酰胺衍生物，其对产生一氧化氮的NO合酶酶活性具有抑制作用，并且对于捕获反应性氧化物种（ROS）也具有作用，因此对于治疗各种疾病是有用的。
• SYDNONE IMINE DERIVATIVES
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0903346A1

  公开（公告）日：1999-03-24

  Compounds represented by the following general formula (1) or pharmaceutically acceptable salts thereof: [wherein Z represents -A-X-R1, a heterocycle or cycloalkyl; A represents a methylene group; X represents a sulfur atom; R1 represents a benzoyl group; R2 represents - N(R3)R4 (wherein R3 represents a methyl group; and R4 represents an optionally substituted alkyl group, etc.); or a group represented by the following general formula (2): wherein R5 and R6 represent each a hydrogen atom; and Y represents a group represented by the following general formula (3): (wherein R4 is as defined above)}]. Because of having vasodilative effect, myocardial protective effect, antiplatelet aggregation effect, etc., the compounds represented by the above general formula (1) or pharmaceutically acceptable salts thereof are useful as drugs such as therapeutic medicines for angina pectoris.

  由以下通式（1）代表的化合物或其药学上可接受的盐类： [其中 Z 代表-A-X-R1、杂环或环烷基；A 代表亚甲基；X 代表硫原子；R1 代表苯甲酰基；R2 代表-N(R3)R4(其中 R3 代表甲基；R4 代表任选取代的烷基等)；或下 列通式(2)所代表的基团： 其中 R5 和 R6 各代表一个氢原子；Y 代表由下式通式 (3) 所代表的基团： (其中 R4 如上定义）}]。 由于具有血管扩张作用、心肌保护作用、抗血小板聚集作用等，上述通式（1）所代表的化合物或其药学上可接受的盐类可用作药物，如心绞痛的治疗药物。
• Medzhidov, A. A.; Farzaliev, V. M.; Kasumov, V. T., Journal of general chemistry of the USSR, 1982, vol. 52, p. 93 - 96
  作者：Medzhidov, A. A.、Farzaliev, V. M.、Kasumov, V. T.、Allakhverdiev, M. A.、Mamedov, Ch. I.

  DOI：——

  日期：——
• Pavlichenko, M. G.; Ivanov, B. E.; Pantukh, B. I., Journal of general chemistry of the USSR, 1985, vol. 55, # 7, p. 1475
  作者：Pavlichenko, M. G.、Ivanov, B. E.、Pantukh, B. I.、Eliseenkov, V. N.、Gershanov, F. B.

  DOI：——

  日期：——