4,5-bis(4-methoxyphenyl)-3H-1,2-dithiole-3-thione | 35564-24-0

• 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)-3H-1,2-dithiole-3-thione
• 英文别名: 4 ,5-bis(4-methoxyphenyl)-1,2-dithiol-3-thione；4,5-Bis-(4-methoxy-phenyl)-[1,2]dithiol-3-thion；4,5-bis(4-methoxyphenyl)dithiole-3-thione
• CAS: 35564-24-0
• 化学式: C₁₇H₁₄O₂S₃
• 分子量: 346.495
• InChiKey: CLEJIKNYKPUJCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,5-bis(4-methoxyphenyl)-3H-1,2-dithiole-3-thione 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到4,5-bis(4-hydroxyphenyl)-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
• 作为产物：
  描述：

  1,2-bis(p-methoxyphenyl)propene 在 sulfur 作用下， 生成 4,5-bis(4-methoxyphenyl)-3H-1,2-dithiole-3-thione
  参考文献：
  名称：

  Schmitt; Suquet, Bulletin de la Societe Chimique de France, 1955, p. 84,86

  摘要：

  DOI：

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。
• Expedient sulfurization with elemental sulfur and an unexpected conversion of 2,3-diarylcyclopropenethiones using tetrabutylammonium fluoride (TBAF) as a source of the fluoride anion
  作者：Grzegorz Mlostoń、Jakub Wręczycki、Amelia Robak、Katarzyna Urbaniak、Dariusz M. Bieliński、Marcin Palusiak、Szymon Sutuła、Krzysztof Woźniak、Heinz Heimgartner

  DOI：10.1016/j.jfluchem.2023.110170

  日期：2023.8

  Elemental sulfur, upon treatment with tetrabutylammonium fluoride (TBAF, 20 mol%) in THF solution at room temperature, undergoes activation via ring opening, leading to in situ-generation of the red colored, highly reactive fluoropolysulfide anion FSx‒. The latter easily reacts with sterically congested 2,3-diarylcyclopropenethiones and five membered 3H-1,2-dithiole-3-thiones are formed selectively

  在室温下，元素硫在 THF 溶液中用四丁基氟化铵（TBAF，20 mol%）处理后，通过开环进行活化，导致原位生成红色、高反应性的氟多硫化物阴离子 FS x –。后者很容易与空间拥挤的2,3-二芳基环丙烯硫酮反应，并以良好至优异的产率选择性地以单一产物形式形成五元3 H -1,2-二硫醇-3-硫酮。在 2,3-双(4-氯苯基)环丙烯酮的情况下观察到通过扩环的类似硫化过程，并且在这种情况下预期的 3 H分离出-1,2-二硫醇-3-酮衍生物，收率83%。详细的方案可以取代已经报道的不太方便的程序，基于 DMF 作为溶剂和氟化钾作为活化剂的应用。在不存在硫的情况下用 TBAF 处理 2,3-二苯基环丙烯硫酮，意外地形成了二聚 α-苯甲酰硫烯酮（去磺胺）的( E,Z )- 和 ( Z,Z )-异构体，并且初步的机制涉及假设最初形成的反应性（α-硫烯酮）苯基亚甲基（一种卡宾物质）作为关键中间体参与其中。