Synthesis And Biological Activity Of Chalcone Derivatives Containing Indone Or Thiazole Oxime Ethe

Chalcone is an important natural product and an important intermediate in the synthesis of flavonoids.Its antibacterial,antiviral,anticancer,anti-inflammatory,insecticidal,antioxidant and other aspects of biological activity is due to theα,β-unsaturated carbonyl and bacteria,viruses and other proteins in the body of the conjugate addition of nucleophilic groups such as mercapto,resulting in death,so it has been widely paid attention to.In this paper,a series of Chalcone derivatives N1-N20 containing indanone and S1-S22 containing thiazoloxime ethers were synthesized by using the principle of active splicing and Chalcone as lead compounds.All of the compounds were characterized by ¹H NMR,¹³C NMR and HRMS.The main research work is summarized as follows:The antiviral activity of the target compound was tested by half leaf spot method.The test results showed that N2 and N7 had good therapeutic activity,with inhibition rates of 68.4 and 68.7%,respectively,better than Ningnanmycin（61.3%）at 500μg/m L.At the same concentration,the inhibition rates of N1,N2 and N10 on TMV were 72.2,74.7 and 76.1%,respectively,which were significantly better than Ningnanmycin（66.3%）,showing good protective activity.Among the compounds of S series,S3,S4,S5,S9,S13,S14,S16 and S18 had good therapeutic activity with inhibition rates of 91.1,74.6,74.0,70.7,77.3,78.5,71.5 and 67.7%,respectively.It was better than Ningnanmycin（64.3%）.The inhibition rates of S3,S7,S8,S9,S14,S17 and S20 on TMV were 73.9,75.1,65.3,65.7,64.9,72.6,69.3%,respectively,which were significantly better than Ningnanmycin（63.5%）,showing good protective activity.Turbidimetric method was used to test the antibacterial activities of the two series of compounds.The results showed that most of the target compounds showed certain inhibitory activities against Pseudomonas syringae pv.altinidiae,Xanthomonas axonopodis pv.Citri,Xanthomonas oryzae pv.oryzae.The antibacterial activity of the target compounds against Phomopsis sp.,Rhizoctonia solani.,Sclerotinia sclerotiorum,Botryosphaeria dothidea,Fusarium asiaticum,Colletotrichum gloeosporioides,Fusarium graminearum,Fusarium dimerum,Fusarium equiseti was tested by mycelium growth rate method.The results showed that the target compounds had certain inhibitory activity against all the tested strains at the concentration of 100μg/m L.Molecular docking experiments showed that there was a hydrogen bond interaction between N2 and ARG-341,the bond length was 3.08（?）.There was A hydrogen bond between Ningnanmycin and ASP-66,and the bond length was 3.72（?）.In contrast,the hydrogen bond length of N2 is shorter,and it binds more tightly.Similarly,S3 formed three strong hydrogen bonds（2.52,2.59,2.79（?）,respectively）with amino acid residues ASN-73,ASP-219 and GLN-257,which were better than those of commercial drug Ningnanmycin（3.15（?））.