sulindac sulfide | 62595-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: sulindac sulfide
• 英文别名: (Z)-2-(5-fluoro-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetic acid；(Z)-2'-des-methyl sulindac sulfide；2-[(3Z)-6-fluoro-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetic acid
• CAS: 62595-28-2
• 化学式: C₁₉H₁₅FO₂S
• 分子量: 326.391
• InChiKey: NEQPIGQSLNSVDO-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sulindac sulfide 反应 10.0h， 生成 (E)-2-(3-(4-(methylthio)benzylidene)-6-fluoro-3H-inden-1-yl)acetic acid
  参考文献：
  名称：

  The influence of double bond geometry in the inhibition of cyclooxygenases by sulindac derivatives

  摘要：

  Sulindac sulfide is a benzylidene-indene that is a potent, time-dependent inhibitor of cyclooxygenases-1 and -2. Removal of the 2'-methyl group from the indene ring dramatically reduces time-dependent inhibition of both enzymes but also changes the geometry of the benzylidene double bond from Z to E. Herein, we explore the importance of double bond geometry on cyclooxygenase inhibition. The Z-isomer of 2'-des-methyl sulindac sulfide was synthesized by reduction of a bromoindene precursor or by photoisomerization of the E-isomer. The Z-isomer inhibited both cyclooxygenases, but with diminished potency compared to sulindac sulfide. Thus, although the 2'-methyl group is a major determinant of time-dependent cyclooxygenase inhibition, the geometry of the benzylidene double bond plays a role as well. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.078
• 作为产物：
  描述：

  (E)-2-(3-(4-(methylthio)benzylidene)-6-fluoro-3H-inden-1-yl)acetic acid 以 二甲基亚砜 为溶剂， 反应 10.0h， 以10%的产率得到sulindac sulfide
  参考文献：
  名称：

  The influence of double bond geometry in the inhibition of cyclooxygenases by sulindac derivatives

  摘要：

  Sulindac sulfide is a benzylidene-indene that is a potent, time-dependent inhibitor of cyclooxygenases-1 and -2. Removal of the 2'-methyl group from the indene ring dramatically reduces time-dependent inhibition of both enzymes but also changes the geometry of the benzylidene double bond from Z to E. Herein, we explore the importance of double bond geometry on cyclooxygenase inhibition. The Z-isomer of 2'-des-methyl sulindac sulfide was synthesized by reduction of a bromoindene precursor or by photoisomerization of the E-isomer. The Z-isomer inhibited both cyclooxygenases, but with diminished potency compared to sulindac sulfide. Thus, although the 2'-methyl group is a major determinant of time-dependent cyclooxygenase inhibition, the geometry of the benzylidene double bond plays a role as well. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.078

文献信息

• Indoleacetic acid and indenacetic acid derivatives as therapeutic agents with reduced gastrointestinal toxicity
  申请人：Marnett J. Lawrence

  公开号：US20050250839A1

  公开（公告）日：2005-11-10

  The presently disclosed subject matter provides derivatives of non-steroidal anti-inflammatory drugs (NSAIDs) that are characterized by substantially reduced cyclooxygenase inhibiting activity, yet retain the ability to interact with and modulate the activities of other polypeptides such as the class of peroxisome proliferators-activated receptors (PPARs) and γ-secretase. Also provided are methods of using the derivatives to treat pathological disorders.

  目前披露的主题提供了非甾体类抗炎药（NSAIDs）的衍生物，其特点是具有明显降低的环氧合酶抑制活性，但仍保留与其他多肽（如过氧化物酶体增殖物激活受体（PPARs）和γ-分泌酶）相互作用和调节活性的能力。还提供了使用这些衍生物治疗病理性疾病的方法。
• INDOLEACETIC ACID AND INDENACETIC ACID DERIVATIVES AS THERAPEUTIC AGENTS WITH REDUCED GASTROINTESTINAL TOXICITY
  申请人：VANDERBILT UNIVERSITY

  公开号：EP1744747A2

  公开（公告）日：2007-01-24
• US7491744B2
  申请人：——

  公开号：US7491744B2

  公开（公告）日：2009-02-17
• US8168656B2
  申请人：——

  公开号：US8168656B2

  公开（公告）日：2012-05-01
• [EN] INDOLEACETIC ACID AND INDENACETIC ACID DERIVATIVES AS THERAPEUTIC AGENTS WITH REDUCED GASTROINTESTINAL TOXICITY<br/>[FR] DERIVES D'ACIDES INDOLEACETIQUE ET INDENACETIQUE COMME AGENTS THERAPEUTIQUES A TOXICITE GASTROINTESTINALE REDUITE
  申请人：UNIV VANDERBILT

  公开号：WO2005112921A2

  公开（公告）日：2005-12-01

  The presently disclosed subject matter provides derivatives of non­steroidal anti-inflammatory drugs (NSAIDs) that are characterized by substantially reduced cyclooxygenase inhibiting activity, yet retain the ability to interact with and modulate the activities of other polypeptides such as the class of peroxisome proliferators-activated receptors (PPARs) and Ϝ-­secretase. Also provided are methods of using the derivatives to treat pathological disorders.