5-(4-(methylsulfonyl)phenyl)-4-phenyl-3H-1,2-dithiole-3-thione | 853301-14-1

• 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: 5-(4-(methylsulfonyl)phenyl)-4-phenyl-3H-1,2-dithiole-3-thione
• 英文别名: 5-(4-methanesulfonylphenyl)-4-phenyl-[1,2]dithiol-3-thione；5-(4-methylsulfonylphenyl)-4-phenyldithiole-3-thione
• CAS: 853301-14-1
• 化学式: C₁₆H₁₂O₂S₄
• 分子量: 364.534
• InChiKey: CLJZUCRQXQYUTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-(methylsulfonyl)phenyl)-4-phenyl-3H-1,2-dithiole-3-thione 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以28%的产率得到5-(4-(methylsulfonyl)phenyl)-4-phenyl-3H-1,2-dithiol-3-one
  参考文献：
  名称：

  Diaryl-dithiolanes and -isothiazoles: COX-1/COX-2 and 5-LOX-inhibitory, OH scavenging and anti-adhesive activities

  摘要：

  Three series of non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the cyclooxygenase/5-lipoxygenase (COX/5-LOX) pathways as such as formation of hydroxyl radicals and adhesion were prepared: 4,5-diaryl isothiazoles, 4,5-diaryl 3H-1,2-dithiole-3-thiones and 4,5-diaryl 3H-1,2-dithiole-3-ones. The aim of the present study was to develop substances which can intervene into the inflammatory processes via different mechanisms of action as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) with increased anti-inflammatory potential. The current lead 11a was evaluated in COX-1/2, 5-LOX and (OH)-O-center dot scavenging in vitro assays and in a static adhesion assay where it proved to inhibit adhesion. Moreover, 11a treatment attenuated expression of macrophage adhesion molecule-1 (Mac-1) on extravasated polymorphonuclear leukocytes (PMNs) which indicates that the activation was reduced. The assays used are predictive for the in vivo efficacy of test compounds as shown for 11a in a peritonitis model of acute inflammation in mice. Thus, the novel 5-LOX/COX and (OH)-O-center dot inhibitor 11a possesses anti-inflammatory activity that, in addition to COX/5-LOX inhibition, implicates effects on leukocyte-endothelial interactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.074
• 作为产物：
  描述：

  1-(4-(methylsulfonyl)phenyl)-2-phenylpropan-1-one 在 劳森试剂 、 sulfur 作用下， 以 联苯 为溶剂， 以6%的产率得到5-(4-(methylsulfonyl)phenyl)-4-phenyl-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Diaryl-dithiolanes and -isothiazoles: COX-1/COX-2 and 5-LOX-inhibitory, OH scavenging and anti-adhesive activities

  摘要：

  Three series of non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the cyclooxygenase/5-lipoxygenase (COX/5-LOX) pathways as such as formation of hydroxyl radicals and adhesion were prepared: 4,5-diaryl isothiazoles, 4,5-diaryl 3H-1,2-dithiole-3-thiones and 4,5-diaryl 3H-1,2-dithiole-3-ones. The aim of the present study was to develop substances which can intervene into the inflammatory processes via different mechanisms of action as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) with increased anti-inflammatory potential. The current lead 11a was evaluated in COX-1/2, 5-LOX and (OH)-O-center dot scavenging in vitro assays and in a static adhesion assay where it proved to inhibit adhesion. Moreover, 11a treatment attenuated expression of macrophage adhesion molecule-1 (Mac-1) on extravasated polymorphonuclear leukocytes (PMNs) which indicates that the activation was reduced. The assays used are predictive for the in vivo efficacy of test compounds as shown for 11a in a peritonitis model of acute inflammation in mice. Thus, the novel 5-LOX/COX and (OH)-O-center dot inhibitor 11a possesses anti-inflammatory activity that, in addition to COX/5-LOX inhibition, implicates effects on leukocyte-endothelial interactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.074

文献信息

• [EN] THIONE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] DERIVES DE THIONE, LEURS PROCEDES DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：CJ CORP

  公开号：WO2005051941A1

  公开（公告）日：2005-06-09

  A 1,2,4-triazole derivative of formula (1) or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

  本发明提供了一种式(1)的1,2,4-三唑衍生物或其非毒性盐，其制备方法以及含有该衍生物或盐作为活性成分的药物组合物。
• Thione Derivative, Method For The Preparation Thereof, And Pharmaceutical Composition Containing The Same
  申请人：Cho Il Hwan

  公开号：US20080090875A1

  公开（公告）日：2008-04-17

  A 1,2,4-triazole derivative of formula 1 or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

  提供了公式1的1,2,4-三唑衍生物或其非毒性盐的制备方法，以及含有该衍生物或盐作为活性成分的药物组合物。
• US7781592B2
  申请人：——

  公开号：US7781592B2

  公开（公告）日：2010-08-24
• Diaryl-dithiolanes and -isothiazoles: COX-1/COX-2 and 5-LOX-inhibitory, OH scavenging and anti-adhesive activities
  作者：Michael Scholz、Holger K. Ulbrich、Oliver Soehnlein、Lennart Lindbom、Andreas Mattern、Gerd Dannhardt

  DOI：10.1016/j.bmc.2008.11.074

  日期：2009.1

  Three series of non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the cyclooxygenase/5-lipoxygenase (COX/5-LOX) pathways as such as formation of hydroxyl radicals and adhesion were prepared: 4,5-diaryl isothiazoles, 4,5-diaryl 3H-1,2-dithiole-3-thiones and 4,5-diaryl 3H-1,2-dithiole-3-ones. The aim of the present study was to develop substances which can intervene into the inflammatory processes via different mechanisms of action as multiple target non-steroidal anti-inflammatory drugs (MTNSAIDs) with increased anti-inflammatory potential. The current lead 11a was evaluated in COX-1/2, 5-LOX and (OH)-O-center dot scavenging in vitro assays and in a static adhesion assay where it proved to inhibit adhesion. Moreover, 11a treatment attenuated expression of macrophage adhesion molecule-1 (Mac-1) on extravasated polymorphonuclear leukocytes (PMNs) which indicates that the activation was reduced. The assays used are predictive for the in vivo efficacy of test compounds as shown for 11a in a peritonitis model of acute inflammation in mice. Thus, the novel 5-LOX/COX and (OH)-O-center dot inhibitor 11a possesses anti-inflammatory activity that, in addition to COX/5-LOX inhibition, implicates effects on leukocyte-endothelial interactions. (C) 2008 Elsevier Ltd. All rights reserved.