S-phenyl o-acetoxythiobenzoate | 88354-10-3

• 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: S-phenyl o-acetoxythiobenzoate
• 英文别名: 2-[(phenylthio)carbonyl]phenyl acetate；2-acetoxy-thiobenzoic acid S-phenyl ester；2-Acetoxy-thiobenzoesaeure-S-phenylester；2-[(Phenylsulfanyl)carbonyl]phenyl acetate；(2-phenylsulfanylcarbonylphenyl) acetate
• CAS: 88354-10-3
• 化学式: C₁₅H₁₂O₃S
• 分子量: 272.324
• InChiKey: SWWTXLHJUAGJBL-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C
• 沸点：
  399.7±34.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯硫酚 、 阿司匹林 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 以84%的产率得到S-phenyl o-acetoxythiobenzoate
  参考文献：
  名称：

  基于硫代羧酸酯的NSAID支架的合成，抗肿瘤活性和分子对接：COX-2抑制和机理研究。

  摘要：

  合成了一系列新的NSAID硫酯，并使用MTT分析法评估了它们对四种人类肿瘤细胞系HepG2，MCF-7，HCT-116和Caco-2的体外抗肿瘤作用。与参考药物5-FU，阿法替尼和塞来昔布相比，化合物2b，3b，6a，7a，7b和8a对选定的肿瘤细胞系表现出有效的广谱抗肿瘤活性。因此，选择这些化合物用于关于COX抑制和激酶测定的机理研究。体外COX-1 / COX-2酶抑制试验结果表明，化合物2b，3b，6a，7a，7b，8a和8b选择性抑制COX-2酶（IC50 =〜0.20-0.69μM），SI值与塞来昔布相比（> 72.5-250）（IC50 = 0.16μM，COX-2 SI：> 312.5）; 但是，所有测试的化合物均未抑制COX-1酶（IC50> 50μM）。另一方面，EGFR，HER2，HER4和cSrc激酶抑制试验的浓度为10μM。选择的候选物对各种测试激酶显示出有限的活性

  DOI：

  10.1080/14756366.2018.1474878

文献信息

• Chemical Feasibility Studies Concerning Potential Prodrugs of Acetylsalicylic Acid.
  作者：Asger B. Hansen、Alexander Senning、Xu Jie-Cheng、Ulla Björkroth、Lu Yi-An、Liu Yin-Zeng

  DOI：10.3891/acta.chem.scand.37b-0351

  日期：——

  A rationale is developed for aspirin prodrugs based on non-acidic latentiated derivatives. Knowledge of the gastro-intestinal liabilities and pharmacological profile is required for this approach whereby aspirin is built into a common ortho ester function of the type 2-substituted 2-methyl-4H-1,3-benzodioxin-4-one with latentiated carboxyl and acetoxy groups. Twelve compounds of this type, ten substituted with various alkoxy and aryloxy groups and two with arylthio groups, have been isolated and characterized. A new synthetic route, comprising the reaction of 2-acetoxybenzoyl chloride with TMS derivatives of the corresponding alcohols and phenols, has been devised for the preparation of some of the compounds while others were prepared according to known methods. Subsequently, the prodrug candidates have been subjected to non-enzymatic hydrolysis for a first rapid screening in vitro. Only 2-tert-butoxy-2-methyl-4H-1,3-benzodioxin-4-one is observed to act as a true proaspirin, releasing aspirin, under these conditions, but analogous compounds with tertiary substituents may display the same behavior, and this chemical approach to aspirin modification may offer a viable rationale for aspirin prodrugs with reduced gastric irritancy or for making "superaspirins".
• Diaz-Mondejar, M. Rosa; Miranda, Miguel A., Heterocycles, 1984, vol. 22, # 5, p. 1125 - 1131
  作者：Diaz-Mondejar, M. Rosa、Miranda, Miguel A.

  DOI：——

  日期：——
• HANSEN, A. B.;SENNING, A., ACTA CHEM. SCAND., 1983, 37, N 4, 351-359
  作者：HANSEN, A. B.、SENNING, A.

  DOI：——

  日期：——
• Synthesis, antitumour activities and molecular docking of thiocarboxylic acid ester-based NSAID scaffolds: COX-2 inhibition and mechanistic studies
  作者：Adel S. El-Azab、Alaa A.-M. Abdel-Aziz、Laila A. Abou-Zeid、Walaa M. El-Husseiny、Ahmad M. El_Morsy、Manal A. El-Gendy、Magda A.-A. El-Sayed

  DOI：10.1080/14756366.2018.1474878

  日期：2018.1.1

  cSrc kinase inhibition assays were evaluated at a 10 μM concentration. The selected candidates displayed limited activities against the various tested kinases; the compounds 2a, 3b, 6a, 7a, 7b and 8a showed no activity to weak activity (% inhibition = ∼0-10%). The molecular docking study revealed the importance of the thioester moiety for the interaction of the drugs with the amino acids in the active

  合成了一系列新的NSAID硫酯，并使用MTT分析法评估了它们对四种人类肿瘤细胞系HepG2，MCF-7，HCT-116和Caco-2的体外抗肿瘤作用。与参考药物5-FU，阿法替尼和塞来昔布相比，化合物2b，3b，6a，7a，7b和8a对选定的肿瘤细胞系表现出有效的广谱抗肿瘤活性。因此，选择这些化合物用于关于COX抑制和激酶测定的机理研究。体外COX-1 / COX-2酶抑制试验结果表明，化合物2b，3b，6a，7a，7b，8a和8b选择性抑制COX-2酶（IC50 =〜0.20-0.69μM），SI值与塞来昔布相比（> 72.5-250）（IC50 = 0.16μM，COX-2 SI：> 312.5）; 但是，所有测试的化合物均未抑制COX-1酶（IC50> 50μM）。另一方面，EGFR，HER2，HER4和cSrc激酶抑制试验的浓度为10μM。选择的候选物对各种测试激酶显示出有限的活性