4-{2-[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]ethoxy}benzaldehyde | 937667-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-{2-[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]ethoxy}benzaldehyde
• 英文别名: 4-[2-[(5-Phenyl-1,3,4-oxadiazol-2-yl)sulfanyl]ethoxy]benzaldehyde
• CAS: 937667-07-7
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: DCPRJHPHWONKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 4-{2-[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]ethoxy}benzaldehyde 在 哌啶乙酸盐 作用下， 以 甲苯 为溶剂， 以91%的产率得到(Z)-5-(4-{2-[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]ethoxy}benzylidene)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring

  摘要：

  Novel thiazolidinedione derivatives were synthesized by incorporating pharmacologically significant heterocycles viz, substituted thiazole, triazole, and oxadiazole moieties linked to the central phenyl ring via heteroatomlinkage with one/two carbon spacer as the structural analogs of Pioglitazone by employing multistep synthetic protocols. Structures of all the newly synthesized intermediates and target molecules were established by analytical and spectral data. These newly synthesized compounds were screened for their invivo hypoglycemic and hypolipidemic activities in male wistar rats. Some of the synthesized compounds demonstrated good activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.015
• 作为产物：
  描述：

  苯甲酸 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 19.0h， 生成 4-{2-[(5-phenyl-1,3,4-oxadiazol-2-yl)thio]ethoxy}benzaldehyde
  参考文献：
  名称：

  设计，合成和生物学评估作为蛋白质酪氨酸磷酸酶1B的非羧酸类抑制剂的芳基丙二腈衍生物

  摘要：

  在这项研究中，我们描述了基于新型非羧基芳基丙二腈的分子作为蛋白质酪氨酸磷酸酶1B（PTP1B）抑制剂的设计，合成，生物学评估和分子建模研究。使用L6肌肉细胞系和针对PTP1B的酶法体外评估了合成的衍生物的葡萄糖再摄取。生物学活性结果表明2-甲氧基取代的（14b）化合物在两种测定中均显示出显着的活性。未取代的化合物（14a）在L6肌肉细胞系中对葡萄糖的再摄取也具有相当的活性，并且在PTP1B酶测定中具有更好的抑制活性。对系列中最有效的化合物进行了对接分析，以了解控制设计分子与PTP1B酶结合的相互作用的性质。

  DOI：

  10.1007/s00044-013-0528-1

文献信息

• Design, synthesis and biological evaluation of novel arylidine-malononitrile derivatives as non-carboxylic inhibitors of protein tyrosine phosphatase 1B
  作者：Girdhar Singh Deora、Chandrabose Karthikeyan、N. S. Hari Narayana Moorthy、Vandana Rathore、Arun K. Rawat、Akhilesh K. Tamrakar、A. K. Srivastava、Piyush Trivedi

  DOI：10.1007/s00044-013-0528-1

  日期：2013.11

  In this study, we describe the design, synthesis, biological evaluation and molecular modelling studies of novel non-carboxylic arylidine malononitrile-based molecules as Protein Tyrosine Phosphatase 1B (PTP1B) inhibitors. The synthesized derivatives were evaluated in vitro for glucose reuptake using L6 muscle cell lines and enzymatic assay against PTP1B. The biological activity results showed that the

  在这项研究中，我们描述了基于新型非羧基芳基丙二腈的分子作为蛋白质酪氨酸磷酸酶1B（PTP1B）抑制剂的设计，合成，生物学评估和分子建模研究。使用L6肌肉细胞系和针对PTP1B的酶法体外评估了合成的衍生物的葡萄糖再摄取。生物学活性结果表明2-甲氧基取代的（14b）化合物在两种测定中均显示出显着的活性。未取代的化合物（14a）在L6肌肉细胞系中对葡萄糖的再摄取也具有相当的活性，并且在PTP1B酶测定中具有更好的抑制活性。对系列中最有效的化合物进行了对接分析，以了解控制设计分子与PTP1B酶结合的相互作用的性质。
• Synthesis, hypoglycemic and hypolipidemic activities of novel thiazolidinedione derivatives containing thiazole/triazole/oxadiazole ring
  作者：A.K. Mohammed Iqbal、Ashraf Y. Khan、Mallikarjun B. Kalashetti、Ningaraddi S. Belavagi、Young-Dae Gong、Imitiyaz Ahmed M. Khazi

  DOI：10.1016/j.ejmech.2012.04.015

  日期：2012.7

  Novel thiazolidinedione derivatives were synthesized by incorporating pharmacologically significant heterocycles viz, substituted thiazole, triazole, and oxadiazole moieties linked to the central phenyl ring via heteroatomlinkage with one/two carbon spacer as the structural analogs of Pioglitazone by employing multistep synthetic protocols. Structures of all the newly synthesized intermediates and target molecules were established by analytical and spectral data. These newly synthesized compounds were screened for their invivo hypoglycemic and hypolipidemic activities in male wistar rats. Some of the synthesized compounds demonstrated good activity. (C) 2012 Elsevier Masson SAS. All rights reserved.