2-(2-methoxyphenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-methoxyphenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole
• 英文别名: 2-(2-methoxyphenyl)-5-pyridin-3-yl-1,3,4-oxadiazole
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: MLBLTIJGNPQULQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲氧基苯甲酸甲酯 在 碘苯二乙酸 、 diazenium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-(2-methoxyphenyl)-5-(pyridin-3-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives and evaluation of their antiglycation potential

  摘要：

  In the search of potent antidiabetic drug, we synthesized 1-25 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives. First, we synthesized 2-methoxybenzohydrazide from methyl 2-methoxybenzoate which was treated with different arylaldehydes to afford 1-25 compounds. The synthesized compounds were evaluated for antiglycation activity. We found that 1-6 and 8 showed potent activity ranging from 160.2 to 290.17 A mu M better than standard drug rutin (IC50 = 295.09 +/- A 1.04 A mu M). All the synthesized compounds were characterized by different spectroscopy methods. These compounds can further be studied to develop lead antidiabetic compounds.

  DOI：

  10.1007/s00044-015-1476-8

文献信息

• A One-Pot Synthesis-Functionalization Strategy for Streamlined Access to 2,5-Disubstituted 1,3,4-Oxadiazoles from Carboxylic Acids
  作者：Daniel Matheau-Raven、Darren J. Dixon

  DOI：10.1021/acs.joc.2c01669

  日期：2022.9.16

  4-oxadiazole synthesis-arylation strategy for accessing 2,5-disubstituted 1,3,4-oxadiazoles, from carboxylic acids, N-isocyaniminotriphenylphosphorane (NIITP), and aryl iodides, is reported. The reaction sequence, featuring a second stage copper-catalyzed 1,3,4-oxadiazole arylation, was found to tolerate (hetero)aryl, alkyl, and alkenyl carboxylic acids, and (hetero)aryl iodide coupling partners. The effectiveness

  报道了一种从羧酸、N-异氰亚氨基三苯基正膦 (NIITP) 和芳基碘化物中获得 2,5-二取代 1,3,4-恶二唑的一锅法 1,3,4-恶二唑合成-芳基化策略。该反应序列具有第二阶段铜催化的 1,3,4-恶二唑芳基化反应，可耐受（杂）芳基、烷基和烯基羧酸，以及（杂）芳基碘化物偶联配偶体。五种含羧酸 API 的后期功能化证明了两阶段策略的有效性，并且还证明了使用N-苯甲酰氧基胺偶联伙伴合成胺化 1,3,4-恶二唑的扩展。
• Structure–activity relationships of tyrosinase inhibitory combinatorial library of 2,5-disubstituted-1,3,4-oxadiazole analogues
  作者：Mahmud Tareq Hassan Khan、Muhammad Iqbal Choudhary、Khalid Mohammed Khan、Mubeen Rani、Atta-ur-Rahman

  DOI：10.1016/j.bmc.2005.03.012

  日期：2005.5

  Here the tyrosinase inhibition studies of library of 2,5-disubstituted-1,3,4-oxadiazoles have been reported and their structure-activity relationship (SAR) also have been discussed. The library of the oxadiazoles was synthesized under the microwave irradiation and was structures of these were characterized by different spectral techniques. From this study it could be concluded that for a better inhibition of tyrosinase, electronegative substitution is essential as most probably the active site of the enzyme contain some hydrophobic site and position is also very important for the inhibition purposes due to the conformational space. The electronegativity of the compounds is somewhat proportional to the inhibitory activity. The compound 3e (3 '-[5-(4 '-bromophenyl)-1,3,4-oxadiazol-2-yl]pyridine) exhibited most potent (IC50 = 2.18 mu M) inhibition against the enzyme tyrosinase which is more potent than the standard potent inhibitor L-mimosine IC50 = 3.68 mu M). This molecule can be the best candidate as a lead compound for further development of drug for the treatments of several skin disorders. (c) 2005 Elsevier Ltd. All rights reserved.
• US6130217A
  申请人：——

  公开号：US6130217A

  公开（公告）日：2000-10-10
• Synthesis of 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives and evaluation of their antiglycation potential
  作者：Muhammad Taha、Nor Hadiani Ismail、Waqas Jamil、Syahrul Imran、Fazal Rahim、Syed Muhammad Kashif、Mohd Zulkefeli

  DOI：10.1007/s00044-015-1476-8

  日期：2016.2

  In the search of potent antidiabetic drug, we synthesized 1-25 2-(2-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole derivatives. First, we synthesized 2-methoxybenzohydrazide from methyl 2-methoxybenzoate which was treated with different arylaldehydes to afford 1-25 compounds. The synthesized compounds were evaluated for antiglycation activity. We found that 1-6 and 8 showed potent activity ranging from 160.2 to 290.17 A mu M better than standard drug rutin (IC50 = 295.09 +/- A 1.04 A mu M). All the synthesized compounds were characterized by different spectroscopy methods. These compounds can further be studied to develop lead antidiabetic compounds.