5-(p-hydroxyphenyl)-3H-1,2-dithiol-3-thione ketoprofen ester

• 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-(p-hydroxyphenyl)-3H-1,2-dithiol-3-thione ketoprofen ester
• 英文别名: [4-(5-Sulfanylidenedithiol-3-yl)phenyl] 2-(3-benzoylphenyl)propanoate
• 化学式: C₂₅H₁₈O₃S₃
• 分子量: 462.614
• InChiKey: DIKBVYMQYKBLKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(4-羟基-苯基)-[1,2]二硫醇-3-硫酮 、 ketoprofen chloride 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 5-(p-hydroxyphenyl)-3H-1,2-dithiol-3-thione ketoprofen ester
  参考文献：
  名称：

  New nuclear transcription factors regulators

  摘要：

  本发明涉及一种新型化合物，这些化合物是核转录因子（NTF）调节剂。本发明还提供了通过调节心血管、结缔组织、肺部、胃肠、呼吸、泌尿生殖、神经或皮肤系统以及肿瘤和感染性疾病中的NTF来治疗、预防和/或减少与炎症相关疾病的方法。本发明基于这样的发现：可以将NTF的调节剂与对治疗心血管、结缔组织、肺部、胃肠、呼吸、泌尿生殖、神经或皮肤系统或肿瘤和感染性疾病有帮助的药理活性化合物联系起来。由此产生的化合物具有良好的生物利用度、增强的活性和/或安全性。

  公开号：

  EP1645288A1

文献信息

• Syntheses, toxicities and anti-inflammation of H 2 S-donors based on non-steroidal anti-inflammatory drugs
  作者：Meng Li、Jili Li、Taofeng Zhang、Quanyi Zhao、Jie Cheng、Bin Liu、Zhen Wang、Libo Zhao、Chenwei Wang

  DOI：10.1016/j.ejmech.2017.06.012

  日期：2017.9

  Three series of H2S donors based on NSAIDs were synthesized and characterized by H-1-NMR, IR and ESIHRMS. The H2S-release abilities of all compounds were evaluated in the presence of TECP or cysteine. The results show all compounds were fast H2S-releasers, and their half-lives were in range of 0-20 min. Under the same condition, H2S released from compound 9 was more than any other compounds. In cytotoxicity aspect, all compounds but 1 and 2 displayed much lower toxicities to both LO2 and HepG2 cell lines, and the IC50 values of most compounds were over 800 mu M. Compounds 1 and 2 had a stronger anti-proliferative activity to both cell lines, but they displayed lower toxicities to LO2 than to HepG2. Based on the cytotoxicity, the developmental toxicities of the compounds were assessed using zebrafish embryos. The results show all tested compounds 2, 9 and 15 had effects on the mortality, hatching rate and spontaneous movements of zebrafish embryos, and caused embryos teratogenesis; and the compounds had dose-dependent toxicities to both embryonic and larval zebrafish. In addition, all compounds had a better anti-inflammatory activity. In the test of anti-inflammatory activities, the tested compounds all reduced the levels of intracellular nitrite and pro-inflammatory cytokines (TNF-alpha, COX-2), increased the levels of anti-inflammatory cytokines (IL-10, HO-1). All these suggest these H2S donors based on NSAIDs have a potential to be a candidate medicine. (C) 2017 Elsevier Masson SAS. All rights reserved.