Visible Light-Promoted Green and Sustainable Approach for One-Pot Synthesis of 4,4’-(Arylmethylene)bis(1H-pyrazol-5-ols), In Vitro Anticancer Activity, and Molecular Docking with Covid-19 M^pro

Abstract

A visible light-promoted, efficient, green, and sustainable strategy has been adopted to unlatch a new pathway toward the synthesis of a library of medicinally important 4,4′-(arylmethylene)bis(1H-pyrazol-5-ols) moieties using substituted aromatic aldehydes and sterically hindered 3-methyl-1-phenyl-2-pyrazoline-5-one in excellent yield. This reaction shows high functional group tolerance and provides a cost-effective and catalyst-free protocol for the quick synthesis of biologically active compounds from readily available substrates. Synthesized compounds were characterized by spectroscopic techniques such as IR, 1 HNMR, 13 CNMR, and single-crystal XRD analysis. All the synthesized compounds were evaluated for their antiproliferative activities against a panel of five different human cancer cell lines and compared with Tamoxifen using MTT assay. Compound 3m exhibited maximum antiproliferative activity and was found to be more active as compared to Tamoxifen against both the MCF-7 and MDA-MB-231 cell lines with an IC 50 of 5.45 and 9.47 μM, respectively. A molecular docking study with respect to COVID-19 main protease (M pro ) (PDB ID: 6LU7 ) has also been carried out which shows comparatively high binding affinity of compounds 3f and 3g (−8.3 and −8.8 Kcal/mole, respectively) than few reported drugs such as ritonavir, remdesivir, ribacvirin, favipiravir, hydroxychloroquine, chloroquine, and olsaltamivir. Hence, it reveals the possibility of these compounds to be used as effective COVID-19 inhibitors.

Visible Light‐Promoted Catalyst‐Free (VLCF) Scalable Synthesis of Novel Derivatives of Isoniazid and Maleimide

“…In medicinal chemistry and drug discovery, VLCF enables the rapid synthesis of heterocyclic scaffolds with enhanced biological activity. [7][8][9][10][11] The technique has also found use in synthesis of advanced materials such as macromolecules, [12] polymers [13,14] and nanomaterials [15,16] for various applications. Furthermore, VLCF's selective activation of specific chemical bonds has opened new avenues for modifying natural products and developing functionalized molecules for industrial applications.…”

“…[1,17] In our recent study, we have successfully synthesized potential anti-cancer spiro indolo-quinazolinone-pyrrolo [3,4-a]pyrrolizine hybrids using a multi-component approach. [7] and 4,4'-(Arylmethylene)bis(1Hpyrazol-5-ols) [8] using the VLCF approach. These compounds exhibited significant anticancer activity, indicating their potential for drug discovery and sustainable organic synthesis, with possible implications in advancing cancer therapeutics.…”

“…The applications of VLCF span various fields of chemistry. In medicinal chemistry and drug discovery, VLCF enables the rapid synthesis of heterocyclic scaffolds with enhanced biological activity [7–11] . The technique has also found use in synthesis of advanced materials such as macromolecules, [12] polymers [13,14] and nanomaterials [15,16] for various applications.…”

Unravelling the Design and Mechanism: Potential of Substituted Quinolines as PASTA subunit 4 Inhibitors for Antimicrobial Activity

“…Nitrogen-containing heterocycles have become a vital and indispensable weapon among bioactive chemicals. [22,23] Because of their diverse range of structures, their diverse synthetic pathways, [24] biological activity, their role in organic catalysis, their ease in going for environment friendly synthesis be like using water as a solvent or solid supported catalyst, [25] transition metal free synthesis, [26] visible light-promoted synthesis, [27] role of new strategies for cancer treatment [28] heterocyclic compounds have become main subject to be explored in pharmaceutical chemistry. Indoles, oxadiazoles, pyrroles, quinolines, pyridines, quinazolines, quinoxalines, pyridones and others are a few of the significant N-containing heterocycles.…”

Photocatalytic activity of Rose Bengal encapsulated in zeolitic imidazolate framework-8 (RB@ZIF-8): an innovative approach for the one pot synthesis of highly functionalized tetrahydropyridines and study of their anti-tubercular activity

“…32 Visible lightdriven synthetic compounds also play a significant role in the medicinal and pharmacological industries. 33 Even though RB is a very efficient photocatalyst, it has a major disadvantage because it is difficult to recover. Therefore, by encapsulating RB into ZIF-8 it is converted into a heterogeneous catalyst, which can be easily recovered and thus can be reused.…”