Synthesis of 5-{[(1Hbenzo[d]imidazol-2-yl)sulfonyl]methyl}-3-phenyl-4,5-dihydroisoxazole derivatives, invitro antibacterial and antioxidant studies along with their insilico analyses

Kotian, Sumana Y.; Husain, Kakul; Rai, Kajal; Saleh, Ebraheem Abdu Musad; Hassan, Iffat; Sabeen, Sabiha

doi:10.1016/j.jscs.2023.101638

Cited by 2 publications

(2 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The DPPH and ABTS •+ acquire stability by taking electrons from MDC and ADC. From scientific literature, , the presence of a methoxy group, a +M substituted group in the para position, and a −M substitution in the meta position favor the antioxidant activity. The methoxy group, an electron donor with beneficial mesomeric action, is present in the core moiety of MDC in the para position.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Rajan,

Karthikeyan,

Desikan

2024

ACS Omega

View full text Add to dashboard Cite

Novel methylenedioxyphenyl-based amides, especially N-(4-methoxybenzyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (MDC) and N-(3-acetylphenyl)-6-nitrobenzo-[1,3]-dioxole-5-carboxamide (ADC), potential cardiovascular preventive agents, are successfully synthesized, and their chemical structures are verified by 1 H and 13 C NMR, Fourier transform infrared (FT-IR), high-resolution mass spectrometry (HRMS), and single-crystal Xray diffraction (SC-XRD) analyses. Data obtained from SC-XRD reveal that MDC and ADC are both monoclinic molecules with Z = 2 and 4, respectively. From density functional theory (DFT) calculations, 3.54 and 3.96 eV are the energy gaps of the optimized MDC and ADC structures, respectively. MDC and ADC exhibit an electrophilicity index value of more than 1.5 eV, suggesting that they can act as an electrophile, facilitating bond formation with biomolecules. Hirshfeld surface analysis demonstrates that more than 25% of atomic interactions in both MDC and ADC are from H•••H interactions. Based on pharmacokinetic predictions, MDC and ADC exhibit drug-like properties, and molecular docking simulations revealed favorable interactions with active site pockets. Both MDC and ADC achieved higher docking scores of −7.74 and −7.79 kcal/mol, respectively, with myeloperoxidase (MPO) protein. From docking results, MPO was found to be most favorable followed by dipeptidyl peptidase-4 (DPP-4) and α-glucosidase (α-GD). Antioxidant, anti-inflammatory, and in vitro enzymatic studies of MDC and ADC indicate that MDC is more selective toward MPO and more potent than ADC. The application of MDC to inhibit myeloperoxidase could be ascertained to reduce the cardiovascular risk factor. This can be supported from the results of computational docking (based on hydrogen bonding and docking score), in vitro antioxidant and anti-inflammatory properties, and MPO enzymatic inhibition (based on the percentage of inhibition and IC 50 values).

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Rajan,

Karthikeyan,

Desikan

2024

ACS Omega

View full text Add to dashboard Cite

show abstract

“…and show a wide range of applications in various disease treatments (such as tuberculosis, leprosy, and dermatitis herpetiformis). 7 Succinimide derivatives show various biological functions, such as antimicrobial, 8 anticonvulsant, 9 antitumor, 10 antiepileptic, 2 anti-inflammatory, 11 and antioxidant activities, 12 and also have structural resemblance to thiazolidinedione (antidiabetic drugs). 13 Similarly, the sulphone moiety shows significant antibacterial, 14 antioxidant, 15 anticancer, 16 antitumor, 17 antidiabetic, 18 antiviral, 19 antifungal, 20 anti-inflammatory, 21 antimalarial 22 and anti-HIV inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

An investigation of the biological applications of sulphonated succinimides: in vivo toxicity to zebrafish larvae as well as antioxidant and antimicrobial potential

Sivanantham,

Senadi,

Ragavendran

et al. 2024

New J. Chem.

View full text Add to dashboard Cite

show abstract

Synthesis of 5-{[(1Hbenzo[d]imidazol-2-yl)sulfonyl]methyl}-3-phenyl-4,5-dihydroisoxazole derivatives, invitro antibacterial and antioxidant studies along with their insilico analyses

Cited by 2 publications

References 26 publications

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

An investigation of the biological applications of sulphonated succinimides: in vivo toxicity to zebrafish larvae as well as antioxidant and antimicrobial potential

Contact Info

Product

Resources

About