2-(benzofuran-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole | 1171243-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(benzofuran-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole
• 英文别名: 2-(1-Benzofuran-2-yl)-5-(4-methylphenyl)-1,3,4-oxadiazole
• CAS: 1171243-26-7
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: KNMTUWXFBDFEND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)-1,3,4-恶二唑 、 2-(2,2-dibromovinyl)phenol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(I) bromide 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以94%的产率得到2-(benzofuran-2-yl)-5-(p-tolyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C–H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles

  摘要：

  In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh3)(2)Cl-2 used as co-catalyst, and (LiOBu)-Bu-t as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 degrees C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.044

文献信息

• Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
  作者：Muhammad Taha、Nor Hadiani Ismail、Syahrul Imran、Abdul Wadood、Fazal Rahim、Syed Muhammad Saad、Khalid Mohammed Khan、Abdul Nasir

  DOI：10.1016/j.bioorg.2016.04.006

  日期：2016.6

  Twenty derivatives of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles (1–20) were synthesized and evaluated for their α-glucosidase inhibitory activities. Compounds containing hydroxyl and halogens (1–6, and 8–18) were found to be five to seventy folds more active with IC50 values in the range of 12.75 ± 0.10–162.05 ± 1.65 μM, in comparison with the standard drug, acarbose (IC50 = 856.45 ± 5

  合成了20种5-芳基-2-（6'-硝基苯并呋喃-2'-基）-1,3,4-恶二唑衍生物（1 – 20），并评估了其对α-葡萄糖苷酶的抑制活性。（含羟基和卤素的化合物1 - 6，和8 - 18被认为是五到70倍带IC多种活性）50个在12.75±0.10-162.05±1.65μM的范围内的值，在与标准药物，阿卡波糖相比（IC 50  = 856.45±5.60μM）。当前的研究探索了α-葡糖苷酶抑制恶二唑和苯并呋喃化合物的混合类。这些发现可能会邀请研究人员从事高血糖治疗领域的研究。对接研究表明，大多数化合物通过氢键和芳烃-芳烃相互作用与重要氨基酸Glu 276，Asp 214和Phe 177相互作用。