Synthesis, in-vitro, in-vivo anti-inflammatory activities and molecular docking studies of acyl and salicylic acid hydrazide derivatives

Munir, Abida; Khushal, Adil; Saeed, Kiran; Sadiq, Abdul; Ullah, Rahim; Ali, Gowhar; Ashraf, Zaman; Mughal, Ehsan Ullah; Jan, Muhammad; Rashid, Umer; Hussain, Izhar; Mumtaz, Amara

doi:10.1016/j.bioorg.2020.104168

Cited by 58 publications

(41 citation statements)

References 27 publications

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“…synthesised 1,3,4-oxadiazole, 1,2,4-triazole, Schiff base, and 3,5-disubstituted pyrazole derivatives starting from salicylic acid and acyl acid hydrazides and tested their inhibitory activity against COX-1 and COX-2. Based on the results, compound 80 ( Figure 13 ) showed excellent COX-2 inhibition, with IC 50 value of 1.76 µM 95 .…”

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 99%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inflammation and disease are closely related. Inflammation can induce various diseases, and diseases can promote inflammatory response, and two possibly induces each other in a bidirectional loop. Inflammation is usually treated using synthetic anti-inflammatory drugs which are associated with several adverse effects hence are not safe for long-term use. Therefore, there is need for anti-inflammatory drugs which are not only effective but also safe. Several researchers have devoted to the research and development of effective anti-inflammatory drugs with little or no side effects. In this review, we studied some small molecules with reported anti-inflammatory activities and hence potential sources of anti-inflammatory agents. The information was retrieved from relevant studies published between January 2019 and May, 2021 for review. This review study was aimed to provide relevant information towards the design and development of effective and safe anti-inflammation agents.

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Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 99%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Fixed oil anti-in ammatory potential in mice Initially, stocksianum xed oil anti-in ammatory effect was determined in mice of both sexes, weighing 25-30 g. The animals have divided arbitrarily into ve groups as 1-5with 06 (n = 6) mice of either sexing each group [53]. Normal saline as a negative control was utilized in Group 1 in 10 ml/kg of body weight.…”

Section: Gc-ms Analysis Of Famesmentioning

confidence: 99%

WITHDRAWN: Identification, Molecular Profiling, Docking Studies and determination of In-vivo Anti-Inflammatory Potential of Teucrium Stocksianum Bioss Fixed Oil (FO)

Shah

Zafar

et al. 2021

Preprint

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Background: Considering the positive and valuable upshots of the naturally occurring ingredients as the complementary treatment for many ailments, this study investigates the Teucrium Stocksianum Bioss Fixed Oil (FO) for the treatment of inflammation.Methods: Different plants of the Teucrium genera have been employed occasionally for the management of different disorders. Teucrium stocksianum (Lamiaceae) is traditionally use as antipyretic along with remedy of inflammation, diabetes and tumors. It also occupies the capacity to purify the blood. The aim of this study is to determine the chemical constituents and anti-inflammatory potentials of Teucrium stocksianum fixed oil (FO). Qualitative and quantitative analysis of fixed oil were performed via GC-MS (Gas Chromatography coupled with Mass Spectrometer). Preliminary inflammation antagonistic activity was calculated in mice using the carrageenan-induced paw edema model while the mechanism behind this inflammatory antagonistic effect was determined by employing various inflammogens including arachidonic acid, prostaglandins E2 and leukotriene via paw edema model.Results: The acute toxicity of fixed oil was determined at 3, 6 and 10 ml/kg body weight of the mouse. The GC-MS analysis documented 21 various unsaturated and saturated fatty acids elements. The methyl esters of octadecadienoic and linoleic acids were found predominantly at 22.60% and 23.84% respectively. In preliminary screening, FO demonstrated substantial anti-inflammatory capacity (67.87%, **P ˂ 0.01) in carrageenan induced paw edema model at 3 ml/kg body weight. The activity reached a peak value at the 3rd hour and continued persistent until the 5th hour of sample administration. FO displayed dose-dependent inhibition against all inflammogens at 3 ml/kg at 3rd h of the FO administration. These have shown marvelous protection i.e. 64.92%, 68.75%and 58.3% against arachidonic acid, prostaglandin E2 and leukotriene accordingly, at 3 ml/kg. The arachidonic acid antagonist (Caffeic acid) demonstrated 69.43% activity at 100 mg/kg after 3rd h of its administration while in the acute toxicity test, FO has shown no grass lethality at 10 ml/kg dose.Conclusion: According to our findings, the FO of T. stocksianum exhibits inflammation antagonistic potential through both lipoxygenase (LOX) and cyclooxygenase (COX) enzyme inhibition strategies that intensely sustenance the traditional practice of T. stocksianum in the management of multiple pathological inflammatory situations. The computed binding energies of the molecules exposed have synergistic potential to avert inflammation.

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“…Synthesis of hydrazide-sulfonamide hybrids (19-36) was carried out starting from the synthesis of substituted hydrazides (10-13) [ 14 ]. For this reason, the methanolic solution of methyl esters (6-9) was refluxed with hydrazine monohydrate 64% to get respective hydrazides (10-13) .…”

Section: Resultsmentioning

confidence: 99%

“…In the 1 H NMR spectrum of the hydrazides (10-13) , a broad singlet of NH appeared at 6.73-9.02 ppm while a broad singlet of the NH 2 group at 3.23-4.26 ppm confirmed the formation of compound (10-13) . Two doublets at 8.07 and 7.96 ppm and a singlet at 6.75 ppm confirmed the presence of all aromatic signals [ 14 ].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Carbonic Anhydrase II/IX/XII Inhibition, DFT, and Molecular Docking Studies of Hydrazide-Sulfonamide Hybrids of 4-Methylsalicyl- and Acyl-Substituted Hydrazide

Khushal

Mumtaz

Shadoul

et al. 2022

BioMed Research International

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Carbonic anhydrases (CAs and EC 4.2.1.1) are the Zn2+ containing enzymes which catalyze the reversible hydration of CO2 to carbonate and proton. If they are not functioning properly, it would lead towards many diseases including tumor. Synthesis of hydrazide-sulfonamide hybrids (19-36) was carried out by the reaction of aryl (10-11) and acyl (12-13) hydrazides with substituted sulfonyl chloride (14-18). Final product formation was confirmed by FT-IR, NMR, and EI-MS. Density functional theory (DFT) calculations were performed on all the synthesized compounds to get the ground-state geometries and compute NMR properties. NMR computations were in excellent agreement with the experimental NMR data. All the synthesized hydrazide-sulfonamide hybrids were in vitro evaluated against CA II, CA IX, and CA XII isozymes for their carbonic anhydrase inhibition activities. Among the entire series, only compounds 22, 32, and 36 were highly selective inhibitors of hCA IX and did not inhibit hCA XII. To investigate the binding affinity of these compounds, molecular docking studies of compounds 32 and 36 were carried out against both hCA IX and hCA XII. By using BioSolveIT’s SeeSAR software, further studies to provide visual clues to binding affinity indicate that the structural elements that are responsible for this were also studied. The binding of these compounds with hCA IX was highly favorable (as expected) and in agreement with the experimental data.

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Synthesis, in-vitro, in-vivo anti-inflammatory activities and molecular docking studies of acyl and salicylic acid hydrazide derivatives

Cited by 58 publications

References 27 publications

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

WITHDRAWN: Identification, Molecular Profiling, Docking Studies and determination of In-vivo Anti-Inflammatory Potential of Teucrium Stocksianum Bioss Fixed Oil (FO)

Synthesis, Carbonic Anhydrase II/IX/XII Inhibition, DFT, and Molecular Docking Studies of Hydrazide-Sulfonamide Hybrids of 4-Methylsalicyl- and Acyl-Substituted Hydrazide

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