Background: Quinoxaline and Tetrahydropyridine derivatives showed various biological properties. The combination of these two scaffolds may contribute to good biological activity and may give novel and efficacious bioactive candidates. Objective: The present study aimed to identify bioactive agents with quinoxaline bearing tetrahydropyridine derivatives possessing anticancer, antioxidant, and anti-tubercular agents. Method: A series of novel quinoxaline bearing tetrahydropyridine derivatives have been designed and synthesized in good yields. The synthetic protocol involves three-component Povarov reactions of 6-amino quinoxaline, propenyl guaethol, and substituted aldehydes using BF3•OEt2 as catalyst. The newly synthesized molecules were evaluated for their anticancer activity against four cell lines, i.e. A-549, MCF-7, PC-3, and HepG2. Results: The results from in vitro assay indicated that compound 4a proved to be as potent as the standard drug adriamycin against all cell lines with GI50 values <10 μg/ml. Compounds 4b, 4f, and 4i exhibited good cytotoxicity against A-549 cell line. All synthesized molecules were evaluated for their antioxidant activity and the results revealed that the compounds 4a, 4b, and 4i showed promising antioxidant activities against DPPH and H2O2 scavenging. In addition, the anti-mycobacterial activity of the synthesized compounds against MTB H37Rv strain was determined using MABA method. The results indicate that the compounds 4a, 4b, 4g, and 4i showed better anti-mycobacterial activity than the standard drugs pyrazinamide, ciprofloxacin and streptomycin with MIC value 1.6 μg/ml. Furthermore, molecular docking studies and ADME properties showed good pharmacokinetic profile and drug-likeness properties. Conclusion: These studies showed that a series of novel quinoxaline bearing tetrahydropyridine derivatives exhibit anticancer, anti-mycobacterial, and antioxidant activities.
Background: Biscoumarin scaffolds are known for their promising pharmacological properties. These compounds have not been studied for their activity against tuberculosis strains. Objective: Unveil the antitubercular properties of biscoumarin scaffolds. Methods: Biscoumarin derivatives (3a-3l) were synthesized using lemon juice as a catalyst and were investigated for their in-vitro anti-tubercular activity against H37Rv strain of Mycobacterium tuberculosis using Microplate Alamar Blue Assay Method (MABA). Their binding interaction was investigated by Molecular Docking Studies using InhA with PDB-ID: 2NSD as target receptors in H37Rv strain of Mycobacterium tuberculosis. These derivatives (3a-3l) were subjected to neutrophil function test. Results: The results revealed that compounds 3b, 3c, 3d, 3f, 3i, 3j showed excellent activity with MIC 1.6 µg/mL. Molecular docking interactions for their antitubercular activity proved that the derivatives (3a-3l) can easily bind into the pockets of InhA enzyme. Neutrophil function test signified that they exhibit moderate neutrophil functions assuring that they do not harm the functioning of Neutrophils. Conclusion: These studies have awakened the property of Biscoumarins as promising anti-tubercular scaffolds.
Background: The occurrence of Tuberculosis (TB) has significantly increased world-wide. The extensively drug-resistant tuberculosis (XDR-TB) and multi-drug resistant tuberculosis (MDR-TB) have made it more challenging to treat this mycobacterial infection caused by the Mycobacterium tuberculosis MTB-H37Rv strain. The present treatments for tuberculosis are of long duration and with side effects. Thus, it is necessary to discover new drugs with short-term chemotherapy, fewer health hazards and cost effectiveness. Objective: The objective of the study was to divulge the antitubercular properties of Betti base scaffolds. Method: Betti bases were designed, synthesized 4a–4h, 6a–6h and investigated for their in vitro anti-tubercular activity using Microplate Alamar Blue assay (MABA) against the MTB-H37Rv strain. Their binding affinity with amino acids was studied by performing molecular docking studies using InhA (PDB ID: 2NSD) present in the MTB-H37Rv strain. Cytotoxicity assay and neutrophil function test (NFT) were also performed. Results: The Betti bases (4a–4h, 6d) showed minimum inhibitory concentration (MIC) values ranging from 1.6 g/mL to 6.25 g/mL against the MTB-H37Rv strain. The compounds (4a–4h, 6a–6h) were investigated for their ADME properties and good pharmacokinetic profiles were observed. In molecular docking studies, a strong binding affinity between InhA and the compounds (4a–4h, 6a–6h) was observed which provided a theoretical insight into the inhibitory action of the synthesized compounds (4a–4h, 6a–6h) against InhA. NFT of the compounds (4a–4h, 6a–6h) showed no harmful effects on the Neutrophils functions. In vitro cytotoxicity assay against Vero cell lines revealed the non-cytotoxic behavior of the compounds. Conclusion: Betti bases can be considered to be a promising class of molecular entities that can lead to the development of new anti-tubercular leads.
Background: Metal oxide and metal oxide nanoparticles are gaining significant importance due to their reusability and wide range of catalytic applications in many organic transformations. Objective: To report simple and efficient Fe3O4 catalyzed one-pot five-component reaction protocol to synthesize novel thiophene containing aminonaphthols under solvent-free conditions. Method: To prepare the Fe3O4 nanoparticles by facile and simple co-precipitation method and surface characterization was done using FT-IR, XRD, BET, SEM, and TEM analysis technique. Aminonaphthol derivatives bearing thiophene moiety were synthesized using Fe3O4 nanoparticles under solvent-free conditions. Results: The prepared nanoparticles are smaller in size (15nm) and can be easily detachable. It can be recycled and reused five times without any significant loss of catalytic activity with excellent yields in a short time. The existing protocol for synthesizing amino naphthol becomes feasible and attractive due to the reusability of the catalyst, excellent catalytic performance, and eco-friendly procedure. Conclusion: In conclusion, Fe3O4 nanoparticles provide a simple, efficient, and greener one-pot five-component synthetic approach to synthesize thiophene containing aminonaphthols. Excellent catalytic activity was perceived in a short reaction time without any co-catalyst or any other activator. Moreover, reusability of catalyst, high yields, and environmentally benign solvent-free condition are vital factors of this protocol.
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