Antioxidant activity of novel 4H- chromene tethered 1,2,3-Triazole Analogues: Synthesis and molecular docking studies

Aitha, Shalini; Thumma, Vishnu; Raghavender, M.; Ambala, Shankaraiah; Jyothi, K. N.; Marmamula, Srinivas; Pochampally, Jalapathi

doi:10.1016/j.rechem.2023.100987

Cited by 6 publications

(10 citation statements)

References 47 publications

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“…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

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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).

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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

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“…The progress of the reaction was monitored by TLC and the full conversion of the aldehydes 11a-b into respective nitrones 10 was achieved within 15 min, at room temperature (rt). All final products were purified by crystallization and their structure and purities were established by 1 H, 13 C, and 19 F NMR (Supplementary Materials, Figures S1-S11), and IR techniques and by elemental analysis (Section 3). In particular, nitrones 10a-d were isolated as pure Zstereoisomers at the double bond (CH=N), as determined and confirmed by the presence of the single sets of the diagnostic signals of the respective protons CH=N (δ = 7.12-7.15 ppm) and CH 2 Ph (δ = 4.97-5.00 ppm) in the 1 H NMR spectra of 10a-d. Based on a comparison of the literature data for other acyclic nitrones [17], Z-configuration was assigned for (Z)-10ad; however, the corresponding signals for the E-isomeric nitrones necessary to provide full correlation were not observed.…”

Section: Chemistrymentioning

confidence: 99%

“…General information-The 1 H, 13 C, and NMR spectra were taken in CDCl 3 on the Bruker Avance III spectrometers (600 MHz, Bruker Instruments, Karlsruhe, Germany) with TMS as the internal standard at 600 and 151 MHz, respectively. The 19 F NMR spectra were recorded in CDCl 3 on the Bruker AvanceNEO (Bruker Instruments, Karlsruhe, Germany) at 565 MHz.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Antioxidant Activity of N-Benzyl-2-[4-(aryl)-1H-1,2,3-triazol-1-yl]ethan-1-imine Oxides

Hadjipavlou-Litina,

Głowacka,

Marco-Contelles

et al. 2024

IJMS

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The synthesis, antioxidant capacity, and anti-inflammatory activity of four novel N-benzyl-2-[4-(aryl)-1H-1,2,3-triazol-1-yl]ethan-1-imine oxides 10a–d are reported herein. The nitrones 10a–d were tested for their antioxidant properties and their ability to inhibit soybean lipoxygenase (LOX). Four diverse antioxidant tests were used for in vitro antioxidant assays, namely, interaction with the stable free radical DPPH (1,1-diphenyl-2-picrylhydrazyl radical) as well as with the water-soluble azo compound AAPH (2,2′-azobis(2-amidinopropane) dihydrochloride), competition with DMSO for hydroxyl radicals, and the scavenging of cationic radical ABTS•+ (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonate) radical cation). Nitrones 10b, 10c, and 10d, having the 4-fluorophenyl, 2,4-difluorophenyl, and 4-fluoro-3-methylphenyl motif, respectively, exhibited high interaction with DPPH (64.5–81% after 20 min; 79–96% after 60 min), whereas nitrone 10a with unfunctionalized phenyl group showed the lowest inhibitory potency (57% after 20 min, 78% after 60 min). Nitrones 10a and 10d, decorated with phenyl and 4-fluoro-3-methylphenyl motif, respectively, appeared the most potent inhibitors of lipid peroxidation. The results obtained from radical cation ABTS•+ were not significant, since all tested compounds 10a–d showed negligible activity (8–46%), much lower than Trolox (91%). Nitrone 10c, bearing the 2,4-difluorophenyl motif, was found to be the most potent LOX inhibitor (IC50 = 10 μM).

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“…Heterocyclic molecules containing oxygen and nitrogen atoms have gained prominence due to their varied pharmacological activities. 23–25 Benzoxazole is one of the most important heterocyclic compounds that exhibit remarkable pharmacological activities 26 such as anticancer, 27 anthelmintic, 28 cyclooxygenase inhibitory, 29 antifungal, 30 antitubercular, 31 5HT3 receptor antagonists, 32 antiinflammatory, 33 analgesic 34 and cyclin-dependent kinase inhibitory, 35 5-lipoxygenase inhibitory, 36 melatonin receptor agonist, 37 antibacterial, 38 antiHIV, 39 anticonvulsant, 40 antiviral, 41 antiallergic, 42 cyclooxygenase 2 (COX-2) inhibitory, 43 antihyperglycemic, 44 dopamine D4 agonists, 43 herbicidal, 45 amyloidogenesis inhibitors, 46 rho kinase inhibitors, 47 and diarrhea-dependent irritable bowel syndrome property. 48 Other than biology, benzoxazoles have various applications such as fluorescent, 49 brighteners, 50 whitening agents, 51 ballistic materials, 52 and sensors.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and cytotoxicity of ibuprofen-appended benzoxazole analogues against human breast adenocarcinoma

Thumma,

Mallikanti,

Matta

et al. 2024

RSC Med. Chem.

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Antioxidant activity of novel 4H- chromene tethered 1,2,3-Triazole Analogues: Synthesis and molecular docking studies

Cited by 6 publications

References 47 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

Synthesis and Antioxidant Activity of N-Benzyl-2-[4-(aryl)-1H-1,2,3-triazol-1-yl]ethan-1-imine Oxides

Design, synthesis, and cytotoxicity of ibuprofen-appended benzoxazole analogues against human breast adenocarcinoma

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