QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

Abstract

QSAR studies of 27 diacyl-hydrazine derivatives containing furan rings were conducted and compared with the DFT method and AM1-MOPAC method. q 2 values of 0.61 and 0.40 validated the predictability and reliability of eq. (5) from the DFT method were higher than those of eq. (6) from the AM1-MOPAC method. The DFT-optimized conformations and ESP-fitting charges of the target compounds were also used for 3D-QSAR analysis, including CoMFA and CoMSIA. The leave-one-out cross-validation correlation coefficient and the good correlation between the predicted and experimental activities of excluded test compounds revealed that CoMFA and CoMSIA models were robust. The QSAR results were consistent with the 3D-QSAR results, indicating that the electrostatic and hydrophobic properties of the target compounds were significant to the biological activity. These models are useful tools for predicting the larvicidal activities of new compounds and designing new specific insect growth regulators. diacyl-hydrazine, QSAR, 3D-QSAR, DFT, insect growth regulator

Synthesis and Fungicidal Activity of Novel 2,5-Disubstituted-1,3,4-oxadiazole Derivatives

“…In our previous work, some benzoylureas, acylhydrazones, diacylhydrazines, semicarbazide, pyrazole, and 1,2,4-triazole derivatives containing 5-phenyl-2-furan moiety were designed and synthesized. All of the compounds showed diverse and promising bioactivities such as insecticidal, fungicidal, and antitumor activities.…”

Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- thiadiazole derivatives containing 5-phenyl-2-furan

“…It has been reported that the compounds containing furan showed broad-spectrum bioactivities. A wide range of derivatives such as dibenzoylureas 15 , diacylhydrazines 16 17 18 19 20 21 , acylhydrazones 22 23 24 25 , semicarbazide 26 , pyrazole, 1,2,4-triazole 27 , 1,3,4-oxadiazole 28 , and carbamic acid esters 29 30 containing 5-phenyl-2-furan moiety has been synthesized and studied in our group for the development of novel chemical entities as a lead molecule in drug and agrochemical discovery. All the compounds showed diverse and significant bioactivities such as fungicidal, insecticidal, and antitumor activities.…”

Synthesis and Larvicidal Activity of Novel Thenoylhydrazide Derivatives

“…General synthetic procedure for 3-(substituted phenyl)-2-thenoic acid. Preparation of different 3-(substituted phenyl)-2-thenoic acid was performed as previously described 40 41 42 43 44 45 46 .…”

“…Encouraged by the above discovery, in our previous work 40 41 42 43 44 45 46 , a series of diacylhydrazines with broad spectrum biological activity were designed and synthesized, and interestingly, the intermediate N - tert -butyl mono-acylhydrazide showed much better insecticidal activity than that of the diacylhydrazide 44 .…”