Anomaly of Pyrano[2,3‐c]pyrazole Synthesis towards Pyrazolyl‐aryl‐methyl‐malononitrile Derivatives and Their Antimicrobial Activity

Abstract

Our attempt to prepare pyrano[2,3-c]pyrazole derivatives from 2-methyl-5-propyl-1,2-dihydro-pyrazolone, malononitrile and benzaldehyde rather lead to the formation of pyrazolyl-arylmethyl-malononitrile derivatives. Fascinating by this opportunity to branch out the synthesis of substituted pyrazolone derivatives using an efficient multicomponent synthetic approach for pyrazolyl-aryl-methyl-malononitrile derivatives. The synthesis was accelerated using guanidine carbonate as a catalyst in the water reaction medium. The rection has blossomed with the green aspects of synthesis such as organo-catalyst, water as reaction medium and ambient temperature providing clean product in higher yield. The synthesized derivatives have been screened for anti-microbial activity. Compounds 4 c and 4 n showed excellent activity. Six compounds were found to be much effective against the Staphylococcus aureus bacterial strain. The molecular docking study of 4 n showed a high binding affinity with the receptor. Collectively, our study provides eco-friendly synthesis towards pyrazolyl-aryl-methyl-malononitrile derivatives and we evaluated them as a new class of anti-microbial compounds.

Copper‐Decorated Magnetite Polydopamine Composite (Fe3O4@PDA): An Effective and Durable Heterogeneous Catalyst for Pyranopyrazole Synthesis

“…The mechanism confirms the experimental results (Scheme 3). [48] A brief review of comparisons with previous work Table 3 shows the comparison and superiority of this catalyst with previously reported works. The results and tests show that the Fe 3 O 4 @PDA/CuCl 2 nanocatalyst for the synthesis of pyranopyrazoles has excellent performance.…”

Choline chloride/urea as a green and efficient deep eutectic solvent in three-component and four-component synthesis of novel pyrazole and pyrano[2,3-c] pyrazole derivatives with antibacterial and antifungal activity

“…Biological properties, such as cytotoxic, mutagenicity, cancer therapy, and antiviral properties, have been reported for the derivatives of the 6-membered heterocyclic compound of pyran with one oxygen in its structure (Yahiaoui et al, 2022). Biological properties, such as anti-tubercular, anti-malarial, antimicrobial, and anti-cancer properties, have been reported for the derivatives of pyrano [2,3-c]pyrazole (Mokariya et al, 2022;Parikh et al, 2022). In addition to the green method of multicomponent reaction, by using other green techniques such as the use of deep eutectic solvents, pyrazole derivatives and pyrano[2,3-c]pyrazole derivatives can be synthesized, and reports have been made in this field (Nguyen et al, 2021;Sikandar and Zahoor, 2021).…”

Indole clubbed 2,4‐thiazolidinedione linked 1,2,3‐triazole as a potent antimalarial and antibacterial agent against drug‐resistant strain and molecular modeling studies

“…[14,16,17] The exploration of indolebased compounds not only addresses these challenges but also holds the potential to overcome existing limitations, providing a crucial step forward in the quest for more effective and versatile antifungal drugs with improved clinical outcomes. Based on recent research findings and previously collected data from sources, [18][19][20][21][22][23][24][25] we propose structures evaluated by the amalgamation of molecular fragments possessing diverse antimicrobial activity as depicted in Figure 1.…”

“…Compounds based on indole-linked 1,2,3-triazole derivatives I, II, III, and IV have demonstrated a wide spectrum of antimicrobial activity. [18,19,24,25] There are two potential sites for structural alteration providing an extensive frame for new design. One is C-3, atom of the indole ring and the other is the N-1 atom of the triazole ring.…”