Synthesis And Biological Activities Of 2-(N-Arylsulfonylindol-3-Yl)-3-N-Acyl-5-Phenyl-1, 3, 4-Oxadiazolines

The N-arylsulfonylindole subunits have gained widespread interest due to their key roles in medically important species,on the other hand, the 1,3,4-oxadiazoline ones exbibit antibacterial activity. Therefore, we want to prepare some 2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-phenyl-1,3,4-oxadiazoline analogs by combining the N-arylsulfonylindole units with the 1,3,4-oxadiazolines together.The topics to synthesis of 3-formylindole as indole the starting materials, further in the preparation of N-arylsulfonyl-3-formylindole, synthesis of N-arylsulfonyl-3-formylindole benzoyl hydrazones from N-arylsulfonyl-3-formylindole and hydrazine. According to the research literatures, synthesis of 1,3,4-oxadiazoline are traditional method that anhydride reflux. This method has many disadvantages, such as the higher temperature reaches 140℃, low yield, and so on. Herein, We not only want to methodological improvements, but also synthesis of the corresponding new 1,3,4-oxadiazoline derivatives. Under ultrasonic irradiation, not only to reduce the shortcomings of traditional method, but also greatly shorten the reaction time and improve productivity. In order to expand the scope of application, we prepared various substituted hydrazone derivatives, including electron-donating and electron-withdrawing substituents, and applied of new method for the synthesis of 2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-phenyl-1,3,4-oxadiazolines(7a-7n) from N-arylsulfonyl-3-formylindole benzoyl hydrazones (5a-5l) and anhydrides (6a-6b) by ultrasonic irradiation.In summary, we have described an efficient and rapid method for the synthesis of 2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-phenyl-1,3,4-oxadiazolines from N-arylsulfonyl-3-formylindole benzoyl hydrazones with acetic or propionic anhydride in good yields under ultrasonic irradiation. Compared to the traditional conditions using stirring, the main advantage of the present procedure is milder conditions and shorter reaction time.We studied are as follows:1: Found a new method of synthesis of 1,3,4-oxadiazoline, and 14 new 2-(N-arylsulfonylindol-3-yl)-3-N-acyl-5-phenyl-1,3,4-oxadiazoline derivatives were synthesized and confirmed by 1H-NMR,MS,HRMS and X-ray crystal analysis.2: Apply mycelium growth rate method, 14 compounds were determined by antifungal activity of five plant pathogenic fungi.3: 4a-4l, 5a-5l compounds were determined by anti-HIV-1 activity.This study provides a new method for synthesis of 1,3,4-oxadiazoline, and provides a theoretical basis to further study of new highly antifungal activity and anti-HIV-1 activity of 1,3,4-oxadiazoline derivatives.