Elastase inhibitory activity of quinoline Analogues: Synthesis, kinetic mechanism, cytotoxicity, chemoinformatics and molecular docking studies

Vanjare, Balasaheb D.; Eom, Young Seok; Raza, Hussain; Hassan, Mubashir; Lee, Ki Hwan; Kim, Song Ja

doi:10.1016/j.bmc.2022.116745

Cited by 10 publications

(5 citation statements)

References 27 publications

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“…The titled compound showed good inhibitory potential against elastase i.e. IC 50 1.21 µM as compared to the oleanolic acid with an IC 50 value of 13.45 µM which has also been reported earlier [ 37 – 40 ] and is shown in Fig. 10 .…”

Section: Resultssupporting

confidence: 78%

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Mustafa,

Channar,

Ejaz

et al. 2023

BMC Chemistry

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A new compound, C23H20BrN3OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å3. The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R22(14) and R22(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.

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Section: Resultssupporting

confidence: 78%

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Mustafa,

Channar,

Ejaz

et al. 2023

BMC Chemistry

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“…Nevertheless, based on the results, LPE was observed to inhibit human elastase activity by more than 70% at concentration of 50 µg/ml is comparable to the positive control in this study. As shown in Table 2, the IC50 of oleanolic acid was similar to a report by Vanjare et al [32] while the IC50 value for LPE of 19.90 ± 1.00 µg/mL was slightly higher than the oleanolic values. Both values were obtained by logarithm curve fitting indicated the concentration of the samples at which 50% of elastase activity was inhibited.…”

Section: Anti-inflammatory Activity Of L Pumila Extractssupporting

confidence: 87%

Anti-inflammatory Activity of Polyphenols from Labisia pumila Leaves Extract

Syed Hassan,

Hasham,

Hashim

et al. 2024

Mal. J. Fund. Appl. Sci.

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Non-Steroidal Anti-inflammatory Drugs (NSAIDs) represent a class of pharmaceutical agents that are frequently misused and misconstrued within the medical landscape. While demonstrably efficacious in providing transient pain relief, NSAIDs do not effectively address the fundamental etiology of pain and are associated with a spectrum of potential adverse effects. Labisia pumila var alata also known as "Kacip Fatimah" has been traditionally used which is attributed to its antioxidant properties. Nonetheless, little attempt has been made to examine its antioxidant and anti-inflammatory characteristics. This study determined the molecular interactions and inhibitory activity profiles of L. pumila methanolic extract (LPE) against the corresponding enzymes via in chemico and in silico approaches. In chemico analysis was done on antioxidant activity and anti-inflammatory properties of L. pumila. The findings indicated that LPE exhibit the potent anti-inflammatory activity. Through high-performance liquid chromatography, it was shown that LPE had the highest gallic acid concentration at 10.74 ± 2.23 mg/mL. LPE did not exhibit cytotoxicity up to 100 µg/mL and displayed optimal protective against UVB-irradiation at 50 µg/mL towards HSF1184 Fibroblast cell line. LPE exhibited potent anti-inflammatory activity as it inhibited elastase and COX-2. Molecular docking studies indicated that gallic acid has a good affinity for collagenase (˗5.68 kcal/mol), elastase (˗4.88 kcal/mol) and COX 2 (˗4.91 kcal/mol). These findings collectively suggested that L. pumila extract has significant potential for the formulation of the natural anti-inflammatory remedies which offer a safer alternative treatment for pain relief, especially for long-term use replacing the conventional NSAIDs medicines.

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“…In addition, the construction of furan heterocycles and chromones by employing rongalite as a C1 synthon has also been realized. These successful examples imply the broad application space of rongalite in the designation of new synthetic methods featuring improved environmental sustainability. , On the other hand, as fundamental and valuable heterocycle moieties with convictive functions, pyridines and quinolines are synthetic targets of longstanding interest in the research of organic synthesis . While aldehydes are usually utilized as the C1 synthons in the construction of pyridine and quinoline rings, searching for alternative C1 synthons has in recent years received high interest for the sake of developing synthetic methods to access more diverse quinoline and pyridine scaffolds with higher efficiency, improved eco-friendliness, and/or new selectivity.…”

Section: Introductionmentioning

confidence: 99%

Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

et al. 2023

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Rongalite has been used as a cheap and efficient carbon synthon for the synthesis of divergent N-heteroaromatics, including different pyridines and quinolines. The selective synthesis of different products can be achieved by employing enaminones or enaminones/anilines as reaction partners. In addition, compared with the reaction using conventional aldehyde synthons, rongalite displays an evident advantage in providing products with considerably higher product yields under milder conditions. The GC–MS analysis of the reaction process has been performed to probe the possible reaction mechanism.

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Elastase inhibitory activity of quinoline Analogues: Synthesis, kinetic mechanism, cytotoxicity, chemoinformatics and molecular docking studies

Cited by 10 publications

References 27 publications

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

Anti-inflammatory Activity of Polyphenols from Labisia pumila Leaves Extract

Rongalite as C1 Synthon in the Synthesis of Divergent Pyridines and Quinolines

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