4-thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate

• 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-thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate
• 英文别名: (4-carbamothioylphenyl) 2-[4-(2-methylpropyl)phenyl]propanoate
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: ACMPXMOACUQISZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-carbamoylphenyl 2-(4-isobutylphenyl)propanoate 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 4.0h， 以55%的产率得到4-thiocarbamoylphenyl 2-(4-isobutylphenyl)propanoate
  参考文献：
  名称：

  HYDROGEN SULFIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS

  摘要：

  本发明涉及具有改善的抗炎性质的非甾体抗炎药（NSAIDs）衍生物，用于治疗炎症、疼痛和发热。更具体地说，非甾体抗炎药与释放硫化氢（H2S）的基团结合，以产生具有减少副作用的新的抗炎化合物。

  公开号：

  US20080004245A1

文献信息

• Toxicities and beneficial protection of H₂S donors based on nonsteroidal anti-inflammatory drugs
  作者：Jinlong Zhang、Qiuping Zhang、Yanni Wang、Jili Li、Zhongjie Bai、Quanyi Zhao、Zhen Wang、Dian He、Jingke Zhang、Yonglin Chen

  DOI：10.1039/c8md00611c

  日期：——

  Based on our previous study, the H₂S donors based on nonsteroidal anti-inflammatory drugs (NSAIDs) were further evaluated including the following aspects: animal blood and urine analyses, liver and kidney toxicities, gastrointestinal protection, anti-hypertension, and myocardial protection.

  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。
• 4-HYDROXYTHIOBENZAMIDE DERIVATIVES OF DRUGS
  申请人：Wallace John L.

  公开号：US20090306412A1

  公开（公告）日：2009-12-10

  Derivatives of drugs are provided, said derivatives comprising the H2S-releasing moiety 4-hydroxythiobenzamide that is either covalently linked to the drug or forms a salt with the drug. The compounds of the present invention exhibit enhanced activity or reduced side effects or both.

  提供药物的衍生物，所述衍生物包括与药物共价结合或形成盐的释放H2S的基团4-羟基硫代苯甲酰胺。本发明的化合物表现出增强的活性或减少的副作用或两者兼备。
• Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
  申请人：Antibe Therapeutics Inc.

  公开号：US07741359B2

  公开（公告）日：2010-06-22

  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.

  本发明涉及非甾体抗炎药（NSAIDs）的衍生物，具有改善的抗炎性能，可用于治疗炎症、疼痛和发热。更具体地说，NSAIDs被衍生出含有氢硫化物（H2S）释放基团的化合物，以产生新型抗炎化合物，具有减少副作用的作用。
• 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.
• US7741359B2
  申请人：——

  公开号：US7741359B2

  公开（公告）日：2010-06-22