Microwave Assisted Synthesis, Characterization and Biological Activities of Ferrocenyl Chalcones and Their QSAR Analysis

Abstract

A new microwave method (MM) has been developed for the synthesis of a series of 16 substituted ferrocenyl chalcones using acetylferrocene (1) with different aldehydes (2a-2p) and comparing it with conventional method (CM). The synthesized compounds were characterized by various spectroscopic techniques viz IR, HR-MS, 1H NMR, and 13C NMR. The time required for completion of reaction in MM varied from 1 to 5 min as compared to CM which required 10–40 h. All the synthesized compounds were screened for antifungal activity against Sclerotium rolfsii and Alternaria solani. In vitro fungicidal activity revealed that compound 3o (ED50 = 23.24 mg L−1) was found to be most active against S. rolfsii. But in case of A. solani, compound 3c (ED50 = 29.9 mg L−1) showed highest activity. The nematicidal activity revealed that the compound 3b was more potent with LC50 values of 10.67, 7.30, and 4.55 ppm at 24, 48, and 72 h, respectively. 2D-Quantitative Structural Activity Relationship (2D-QSAR) analysis of these ferrocenyl chalcones was carried out by developing three different models namely Partial Least Squares (PLS, Model 1), Multiple Linear Regression (MLR, Model 2) and Principal Component Regression (PCR, Model 3). Statistical significance and predictive ability of these models were assessed by internal and external validation and also verified by leave one-out cross-validation. QSAR study revealed that MLR for S. rolfsii (r2 = 0.999, q2 = 0.996), PLS for A. solani (r2 = 0.934, q2 = 0.749) and PCR for M. incognita (r2 = 0.878, q2 = 0.772) were the best model. The physico-chemical parameters were calculated using VLife MDS 4.6 software. QSAR study could be employed for structure optimization to achieve better activity.

Novel Galactosyl Moiety-Conjugated Furylchalcones Synthesized Facilely Display Significant Regulatory Effect on Plant Growth

“…9−12 Recently, it has been reported that chalcones have been served as novel insecticides to control insect population, such as angular benzofuran chalcones, 13 chemically modified chalcones, 14 the chalcone derivatives kanakugiol, hydroxychalcone and cardamonin, 15 and furan-chalcones. 16 Moreover, the fungistatic and fungicidal effects of chalcones have also been investigated against phytopathogens in greater detail, including geranyl chalcones, 17 chalcone-based strobilurins, 18 dihydrochalcones (mainly phloridzin, sieboldin, trilobatin, and phloretin), 19 vanillin-chalcones, 20 ferrocenyl-chalcones, 21 isobavachalcones, 22 dihydrochromane-chalcones, 23 and isobavachalcones. 24 In contrast, the herbicidal activity of chalcones has been less investigated.…”

“…These compounds or chalcone-rich plant extracts have competed for substantial research attention as drugs or food preservatives for decades. , Chalcones exhibit numerous interesting biological activities such as anti-cancer, anti-inflammatory, anti-hypertensive, anti-oxidant, anti-viral, anti-bacterial, and anti-microbial activities, which were several times reviewed. − Recently, it has been reported that chalcones have been served as novel insecticides to control insect population, such as angular benzofuran chalcones, chemically modified chalcones, the chalcone derivatives kanakugiol, hydroxychalcone and cardamonin, and furan-chalcones . Moreover, the fungistatic and fungicidal effects of chalcones have also been investigated against phytopathogens in greater detail, including geranyl chalcones, chalcone-based strobilurins, dihydrochalcones (mainly phloridzin, sieboldin, trilobatin, and phloretin), vanillin-chalcones, ferrocenyl-chalcones, isobavachalcones, dihydrochromane-chalcones, and isobavachalcones . In contrast, the herbicidal activity of chalcones has been less investigated.…”

Antinemic activity of ferrocenyl chalcones against Meloidogyne incognita infestation in tomato

“…The need of the present is to develop environmentally safe alternative for effective nematode control. Several natural and synthetic derivatives have been found effective against M. incognita , Bose et al 2010, Attar et al 2011, Kaushik et al 2015, Caboni et al 2016, Yadav et al 2019. In the present study, the bioefficacy evaluation of most potent molecules, identified on the basis of in vitro results, is reported in pot cultured tomato cv.…”

The Synthesis and Anti-cancer Activities of Ferrocenyl Chalcones; Drug-Likeness Calculations

“…On the other hand, ferrocenyl chalcone synthesis and their biological evaluations were well studied. Yadav et al synthesized 16 ferrocenyl chalcone through using microwave in high yields and screened them for antifungal against Sclerotium rolfsii and Alternaria solani (Yadav et al, 2019). They have found that their chalcones showed good antifungal activity.…”