4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 4-isobutyl-α-methyl-phenylacetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 4-isobutyl-α-methyl-phenylacetate
• 英文别名: [4-(5-Sulfanylidenedithiol-3-yl)phenyl] 2-[4-(2-methylpropyl)phenyl]propanoate；[4-(5-sulfanylidenedithiol-3-yl)phenyl] 2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₂₂H₂₂O₂S₃
• 分子量: 414.613
• InChiKey: HZLSKDUFCSAUBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(4-羟基-苯基)-[1,2]二硫醇-3-硫酮 、 布洛芬 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以44.1%的产率得到4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl 4-isobutyl-α-methyl-phenylacetate
  参考文献：
  名称：

  Toxicities and beneficial protection of H₂S donors based on nonsteroidal anti-inflammatory drugs

  摘要：

  根据我们先前的研究，基于非甾体抗炎药（NSAIDs）的H₂S供体进一步评估，包括以下方面：动物血液和尿液分析，肝肾毒性，胃肠保护，抗高血压和心肌保护。

  DOI：

  10.1039/c8md00611c

文献信息

• EP2889294
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• US8541398B2
  申请人：——

  公开号：US8541398B2

  公开（公告）日：2013-09-24
• [EN] HYDROGEN SULFIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS<br/>[FR] DÉRIVÉS DE SULFURE D'HYDROGÈNE D'ANTI-INFLAMMATOIRES NON STÉROÏDIENS
  申请人：ANTIBE THERAPEUTICS INC

  公开号：WO2008009127A1

  公开（公告）日：2008-01-24

  [EN] The present invention relates to derivatives of non-steroidal anti-inflammatory drugs (NSAIDs) having improved anti-inflammatory properties useful in the treatment of inflammation, pain and fever. More particularly, NSAIDs are derivatized with a hydrogen sulfide (H₂S) releasing moiety to produce novel anti-inflammatory compounds having reduced side effects.
  [FR] La présente invention concerne des dérivés d'anti-inflammatoires non stéroïdiens (AINS) présentant de meilleures propriétés anti-inflammatoires utiles pour traiter l'inflammation, la douleur et la fièvre. Plus particulièrement, ces anti-inflammatoires non stéroïdiens (AINS) sont dérivés avec un groupe de libération de sulfure d'hydrogène (H₂S) afin qu'on obtienne de nouveaux composés anti-inflammatoires présentant des effets secondaires réduits.