4-((5-苯基戊基)硫代)苯酚 | 273939-24-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 4-((5-苯基戊基)硫代)苯酚
• 英文名称: 4-((5-phenylpentyl)thio)phenol
• 英文别名: 4-(5-phenylpentylsulfanyl)phenol
• CAS: 273939-24-5
• 化学式: C₁₇H₂₀OS
• 分子量: 272.411
• InChiKey: MRKUOIJRHDPXHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((5-苯基戊基)硫代)苯酚 在 二异丁基氢化铝 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Hydroxy-3-[4-(5-phenylpentylsulfanyl)phenoxy]propanenitrile
  参考文献：
  名称：

  Design of novel and potent cPLA2α inhibitors containing an α-methyl-2-ketothiazole as a metabolically stable serine trap

  摘要：

  We report the design of novel, potent cPLA(2)alpha inhibitors that possess an alpha-methyl-2-ketothiazole that acts as a serine-reactive moiety. We describe the optimization of the series for potency and metabolic stability towards ketone reduction. This was achieved by attenuating the reactivity of the ketone using a combination of electronic and steric effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.005
• 作为产物：
  描述：

  4-羟基苯硫酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 4-((5-苯基戊基)硫代)苯酚
  参考文献：
  名称：

  Synthesis and evaluation of substrate-mimicking cytosolic phospholipase A 2 inhibitors––reducing the lipophilicity of the arachidonyl chain isostere

  摘要：

  The high lipophilicity of a series of cytosolic phospholipase A(2) inhibitors has been reduced by the modification of a decyloxyphenyl chain designed to mimic the arachidonyl group of the natural substrate. These changes have resulted in an improvement in the whole cell potency of the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.024

文献信息

• Design and Synthesis of a Novel and Potent Series of Inhibitors of Cytosolic Phospholipase A₂ Based on a 1,3-Disubstituted Propan-2-one Skeleton
  作者：Stephen Connolly、Colin Bennion、Sarah Botterell、Pamela J. Croshaw、Catherine Hallam、Kim Hardy、Paul Hartopp、Clive G. Jackson、Sarah J. King、Louise Lawrence、Antonio Mete、David Murray、David H. Robinson、Gillian M. Smith、Linda Stein、Iain Walters、Edward Wells、W. John Withnall

  DOI：10.1021/jm011050x

  日期：2002.3.1

  Using knowledge of the substrate specificity of cPLA(2) (phospliolipases A(2)), a novel series of inhibitors of this enzyme were designed based upon a three point model of inhibitor binding to the enzyme active site comprising a lipophilic anchor, an electrophilic serine "trap", and an acidic binding moiety. The resulting 1,3-diheteroatom-substituted propan-2-ones were evaluated as inhibitors of cPLA2 in both aggregated bilayer and soluble substrate assays. Systematic variation of the lipophilic, electrophilic, and acidic groups revealed a well-defined structure-activity relationship against the enzyme. Optimization of each group led to compound 22 (ARC70484XX), which contains a decyloxy lipophilic side chain, a 1,3-diaryloxypropan-2-one moiety as a unique serine trap, and a benzoic acid as the acidic binding group. AR-C70484XX was found to be among the most potent in vitro inhibitors of cPLA2, described to date being more than 20-fold more active against the isolated enzyme (IC50 = 0.03 muM) than the standard CPLA(2) inhibitor, arachidonyl trifluoromethyl ketone (AACOCF(3)), and also greater than 10-fold more active than AACOCF3 against the cellular production of arachidonic acid by HL60 cells (IC50 = 2.8 muM).
• NOVEL COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1135377A1

  公开（公告）日：2001-09-26
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES
  申请人：ASTRAZENECA UK LTD

  公开号：WO2000034254A1

  公开（公告）日：2000-06-15

  Compounds of formula (I) are disclosed, processes for their preparation, pharmaceutical compositions containing the compounds and the use of the compounds as pharmaceuticals. There are also provided chemical intermediates useful for the preparation of the compounds. The compounds are useful as pharmaceuticals, especially for the treatment of inflammatory disease.
• Synthesis and evaluation of substrate-mimicking cytosolic phospholipase A 2 inhibitors––reducing the lipophilicity of the arachidonyl chain isostere
  作者：Iain Walters、Colin Bennion、Stephen Connolly、Pamela J Croshaw、Kim Hardy、Paul Hartopp、Clive G Jackson、Sarah J King、Louise Lawrence、Antonio Mete、David Murray、David H Robinson、Linda Stein、Edward Wells、W John Withnall

  DOI：10.1016/j.bmcl.2004.05.024

  日期：2004.7

  The high lipophilicity of a series of cytosolic phospholipase A(2) inhibitors has been reduced by the modification of a decyloxyphenyl chain designed to mimic the arachidonyl group of the natural substrate. These changes have resulted in an improvement in the whole cell potency of the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.
• Design of novel and potent cPLA2α inhibitors containing an α-methyl-2-ketothiazole as a metabolically stable serine trap
  作者：Antonio Mete、Glen Andrews、Mike Bernstein、Stephen Connolly、Paul Hartopp、Clive G. Jackson、Richard Lewis、Iain Martin、David Murray、Rob Riley、David H. Robinson、Gill M. Smith、Edward Wells、W. John Withnall

  DOI：10.1016/j.bmcl.2011.03.005

  日期：2011.5

  We report the design of novel, potent cPLA(2)alpha inhibitors that possess an alpha-methyl-2-ketothiazole that acts as a serine-reactive moiety. We describe the optimization of the series for potency and metabolic stability towards ketone reduction. This was achieved by attenuating the reactivity of the ketone using a combination of electronic and steric effects. (C) 2011 Elsevier Ltd. All rights reserved.