2-Hydroxy-1-(4-methylsulfanylphenyl)-2-phenylethanone | 860699-91-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-Hydroxy-1-(4-methylsulfanylphenyl)-2-phenylethanone
• CAS: 860699-91-8
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: IXVJAFAWXWZPPF-UHFFFAOYSA-N

物化性质

• 沸点：
  441.1±35.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-1-(4-methylsulfanylphenyl)-2-phenylethanone 以 甲醇 、 正丁醇 为溶剂， 反应 18.0h， 生成 2-methylsulfonyl-5-(4-methylsulfonylphenyl)-4-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1 H -imidazole derivatives

  摘要：

  A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesized compounds, 2-alkylthio series were more potent and selective than 2-sulfonylalkyl derivatives. In molecular modeling, interaction of 2-sulfonylalkyl moiety with Arg120 in COX-1 and an extra hydrogen bond with Tyr341 in COX-2 increased the residence time of ligands in the active site in 2-sulfonylalkyl and 2-alkylthio analogs, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.058
• 作为产物：
  描述：

  乙酮,2-溴-1-[4-(甲硫基)苯基]-2-苯基- 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 2-Hydroxy-1-(4-methylsulfanylphenyl)-2-phenylethanone
  参考文献：
  名称：

  Synthesis, cyclooxygenase inhibitory effects, and molecular modeling study of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and -2-alkylsulfonyl-1 H -imidazole derivatives

  摘要：

  A series of 4-aryl-5-(4-(methylsulfonyl)phenyl)-2-alkylthio and 2-alkylsulfonyl-1H-imidazole derivatives were synthesized. All compounds were tested in human blood assay to determine COX-1 and COX-2 inhibitory potency and selectivity. Among the synthesized compounds, 2-alkylthio series were more potent and selective than 2-sulfonylalkyl derivatives. In molecular modeling, interaction of 2-sulfonylalkyl moiety with Arg120 in COX-1 and an extra hydrogen bond with Tyr341 in COX-2 increased the residence time of ligands in the active site in 2-sulfonylalkyl and 2-alkylthio analogs, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.058

文献信息

• 2, 3-Diaryl-5-ethylsulfanylmethyltetrahydrofurans as a new class of COX-2 inhibitors and cytotoxic agents
  作者：Palwinder Singh、Anu Mittal、Satwinderjeet Kaur、Wolfgang Holzer、Subodh Kumar

  DOI：10.1039/b803608j

  日期：——

  2,3-Diaryl-5-ethylsulfanylmethyltetrahydrofuran-3-ols were designed and synthesized by the allylations of benzoins followed by iodocyclization and nucleophilic replacement reactions with ethanthiol. These molecules exhibit IC50 for COX-2 at <10 nM concentration and exhibit average GI50 over all the 59 human tumor cell lines at μM concentration.

  通过安息香类化合物的烯丙基化反应，然后与乙硫醇进行碘代环化和亲核置换反应，设计并合成了 2,3-二芳基-5-乙硫甲基四氢呋喃-3-醇。这些分子对 COX-2 的 IC50 小于 10 nM，对所有 59 种人类肿瘤细胞株的平均 GI50 为 μM。