4,5-Bis(4-methoxyphenyl)-1,2-dithiol-3-on | 81385-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-Bis(4-methoxyphenyl)-1,2-dithiol-3-on
• 英文别名: 4,5-bis(4-methoxyphenyl)-1,2-dithiol-3-one；4,5-bis(4-methoxyphenyl)-3H-1,2-dithiol-3-one；4,5-bis(4-methoxyphenyl)dithiol-3-one
• CAS: 81385-76-4
• 化学式: C₁₇H₁₄O₃S₂
• 分子量: 330.428
• InChiKey: HXHFMMHFTDDRIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-bis(4-methoxyphenyl)-3H-1,2-dithiole-3-thione 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 生成 4,5-Bis(4-methoxyphenyl)-1,2-dithiol-3-on
  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

• Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments
  作者：Jessica J. Sánchez García、Rene S. Joo-Cisneros、David García-Bassoco、Marcos Flores-Alamo、José M. Méndez Stivalet、Jesús García-Valdés、Elena I. Klimova

  DOI：10.1016/j.jorganchem.2021.121809

  日期：2021.7

  A new synthesis method was established for 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones, from different cyclopropenones: diphenyl (a), bis-(4-methoxyphenyl (b), diferrocenyl (c) and diruthenocenyl (d), in the presence of elemental sulfur with yields of the 5a-d (35-57%), or in the presence of the additive NaHS, with yields of the 5a-d (45-72%) and 6a-d (10-18%). The characterization of the new compounds

  建立了一种新的合成方法，用于合成来自不同环丙烯的1,2-二硫醇-3-酮和1,2-二硫醇-3-硫酮：二苯基（a），双-（4-甲氧基苯基（b），二铁茂铁（c）和diruthenocenyl（d），在元素硫的存在下与所述的收率图5a-d（35-57％），或在添加剂硫氢化钠的存在下，与所述的收率图5a-d（45-72％）和6a中-d（10-18％）。通过IR，1 H和13 C NMR光谱，元素分析，质谱对新化合物进行表征，此外，对化合物5a，b， d进行了。使用循环（CV），微分脉冲（DPV）和方波（SWV）伏安法研究了杂环化合物的氧化还原特性。
• Behringer, Hans; Meinetsberger, Eike, Liebigs Annalen der Chemie, 1982, # 2, p. 315 - 341
  作者：Behringer, Hans、Meinetsberger, Eike

  DOI：——

  日期：——
• BEHRINGER, H.;MEINETSBERGER, E., LIEBIGS ANN. CHEM., 1982, N 2, 315-341
  作者：BEHRINGER, H.、MEINETSBERGER, E.

  DOI：——

  日期：——
• 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.