Design, Synthesis, Pharmacological Evaluation and Molecular Docking Studies of Substituted Oxadiazolyl-2-Oxoindolinylidene Propane Hydrazide Derivatives

Kerzare, Deweshri; Chikhale, Rupesh; Bansode, Ratnadeep; Amnerkar, Nikhil D.; Karodia, Nazira; Paradkar, Anant; Khedekar, Pramod B.

doi:10.5935/0103-5053.20160090

Cited by 13 publications

(16 citation statements)

References 12 publications

(22 reference statements)

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“…Among the phytochemicals studied were a-Terpineol (Oliveira et al, 2016;Gouveia et al, 2018); 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N′-[2-oxo-1,2-dihydro-3H-indol-3ylidene] propane hydrazide (Kerzare et al, 2016); b-cyclodextrin (CT-bCD) complexed with citronellal (CT) (Santos et al, 2016); (−)-a-bisabolol (Melo et al, 2017;Teixeira, et al, 2017); bcyclodextrin complexed with farnesol (Silva et al, 2017), and p-Cymene (Santos et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…Assis et al (Santos et al, 2016;Gouveia et al, 2018Santos et al, 2019. The in silico programs used for docking studies were; Molegro Virtual Docker (Oliveira et al, 2016;Siqueira-Lima et al, 2017;de Oliveira Juńior et al, 2018;Gouveia et al, 2018;Leite et al, 2019;Santos et al, 2019); Sybyl ® X software suite (Garcıá et al, 2011), Vlife MDS (Kerzare et al, 2016); AutoDock Vina (Santos et al, 2016); Hex Protein Docking (HEX) (Teixeira et al, 2017;Melo et al, 2017); and AutoDock 4.2 software in PyRx 0.9 (Silva et al, 2017).…”

Section: Resultsmentioning

confidence: 99%

“…The molecular targets/complexes used in the docking studies were Nitric Oxide Synthase (Gouveia et al, 2018), COX-2 (Garcıá et al, 2011;Sumiwi et al, 2015;Kerzare et al, 2016); GluR2-S1S2 (Santos et al, 2016); TRPV1 (Teixeira et al, 2017;Melo et al, 2017); b-CD complex (Silva et al, 2017); CaV1, CaV2.1, CaV2.2, and CaV2.3 (Santos et al, 2019); 5-HT receptor, Delta receptor, Kappa receptor, and MU (µ) receptor (Oliveira et al, 2016); Alpha Adrenergic, Opioid, and Serotonergic receptors (Siqueira-Lima et al, 2017); Muscarinic receptors and GABA A (De Oliveira Junior et al, 2017; de Oliveira Juńior et al, 2018); Opioid and Serotonin receptors (Quintans-Junior et al, 2018); 5-HT 3 and M2 receptors (Leite et al, 2019).…”

Section: Docking Of Antinociceptive Essential Oilsmentioning

confidence: 99%

“…Hydrophobic interactions were found mainly at GLN374 and ARG376. Compound 51 also stood out for interacting at the COX-2 active site, forming two hydrogen bonds at ASN375 (Kerzare et al, 2016). The presence of methyl or hydroxyl groups, as well as a 1,3,4oxadiazole nitro substitution, increased the activity.…”

Section: Propanehydrazide Derivativesmentioning

confidence: 99%

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Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

et al. 2020

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Introduction: Pain is considered an unpleasant sensory and emotional experience, being considered as one of the most important causes of human suffering. Computational chemistry associated with bioinformatics has stood out in the process of developing new drugs, through natural products, to manage this condition. Objective: To analyze, through literature data, recent molecular coupling studies on the antinociceptive activity of essential oils and monoterpenes. Data source: Systematic search of the literature considering the years of publications between 2005 and December 2019, in the electronic databases PubMed and Science Direct. Eligibility Criteria: Were considered as criteria of 1) Biological activity: non-clinical effects of an OE and/or monoterpenes on antinociceptive activity based on animal models and in silico analysis, 2) studies with plant material: chemically characterized essential oils and/or their constituents isolated, 3) clinical and non-clinical studies with in silico analysis to assess antinociceptive activity, 4) articles published in English. Exclusion criteria were literature review, report or case series, meta-analysis, theses, dissertations, and book chapter. Results: Of 16,006 articles, 16 articles fulfilled all the criteria. All selected studies were non-clinical. The most prominent plant families used were Asteraceae, Euphorbiaceae, Verbenaceae, Lamiaceae, and Lauraceae. Among the phytochemicals studied were a-Terpineol, 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N′-[2-oxo-1,2-dihydro-3H-indol-3ylidene] propane hydrazide, b-cyclodextrin complexed with citronellal, (−)-a-bisabolol, b-cyclodextrin complexed with farnesol, and p-Cymene. The softwares used for docking studies were Molegro Virtual Docker, Sybyl ® X, Vlife MDS, AutoDock Vina, Hex Protein Docking, and AutoDock 4.2 in PyRx 0.9. The molecular targets/complexes used were Nitric Oxide Synthase, COX-2, GluR2-S1S2, TRPV1, b-CD complex, CaV 1 , CaV 2.1 , CaV 2.2 , and CaV 2.3 , 5-HT receptor, delta receptor, kappa receptor, and MU (m)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Docking Of Antinociceptive Essential Oilsmentioning

confidence: 99%

Section: Propanehydrazide Derivativesmentioning

confidence: 99%

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Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

et al. 2020

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“…Substitution of the halogen atom in the aromatic ring resulted in the formation of less active compounds. 55 Hybrid molecules were synthesized by combining quinazoline substituted at position # 2 with an aromatic ring and isatin, which is an oxidized form of indole, based on the wide variety of biological activities of these scaffolds. In the newly synthesized compounds 2-methyl substituted derivative showed more analgesic and antiinflammatory activity as compared to 2-phenyl derivatives.…”

Section: Hybrid Molecules Having Indole and Oxindole Ringsmentioning

confidence: 99%

Hybrid organic molecules as antiinflammatory agents; a review of structural features and biological activity

Mohsin¹,

Ahmad²

2018

Turk J Chem

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Nonsteroidal antiinflammatory drugs (NSAIDs) are widely used for the treatment of pain and inflammation.Some undesirable effects are linked with NSAIDs such as the gastrointestinal tract (GIT) toxicity and cardiovascular disturbances. At present the preparation of a hybrid molecular technique is being used to produce new analgesic and antiinflammatory molecules. Attachment of NSAIDs with nitric oxide and hydrogen sulfide releasing molecules produced some gastroprotective agents with improved analgesic and antiinflammatory activities. Combination of NSAIDs with different biologically active 5-membered, 6-membered, and condensed heterocyclic rings has also led to the formation of some potent molecules. Some of these hybrid molecules, e.g., ibuprofen-thiazole, exhibited less GIT toxicity, while others showed selectivity for COX-2 enzyme, e.g., quinazolinone-pyrimidine and benzothiophene-rhodanine hybrids. COX-2 selectivity was also exhibited by hybrids of NSAIDs with natural molecules such as salicylates-resveratrol, chromoneoxindole, and chrysin-indole-pyrazole. The preparation of new hybrid molecules is significant because they can serve as a lead compound for the discovery and development of safer analgesic and antiinflammatory agents.

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Development of novel indole‐linked pyrazoles as anticonvulsant agents: A molecular hybridization approach

Kerzare

Menghani

Rarokar

et al. 2020

Archiv der Pharmazie

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A series of 3‐{2‐[1‐acetyl‐5‐(substitutedphenyl)‐4,5‐dihydropyrazol‐3‐yl]hydrazinylidene}‐1,3‐dihydro‐2H‐indol‐2‐ones 24–43 was synthesized using an appropriate synthetic route and evaluated experimentally by the maximal electroshock test. These compounds were evaluated for antidepressant and antianxiety activities. The most active compound, 3‐{2‐[1‐acetyl‐5‐(4‐chlorophenyl)‐4,5‐dihydropyrazol‐3‐yl]hydrazinylidene}‐1,3‐dihydro‐2H‐indol‐2‐one 25, exhibited an ED50 of 13.19 mmol/kg, a TD50 of 43.49 mmol/kg, and a high protective index of 3.29, compared with the standard drug diazepam. To get insights into the intermolecular interactions, molecular docking studies were performed at the active site of the GABAA receptor and the MAO‐A enzyme. Molecular docking studies are also in agreement with the pharmacological evaluation with potent compounds, exhibiting docking scores of −1.5180 and 0.7458 for the GABAA receptor and MAO‐A, respectively. The 3D‐QSAR analysis was carried out by Vlife MDS engine 4.3.1, and a statistically reliable model with good predictive power (r2 = 0.7523, q2 = 0.3773) was achieved. The 3D‐QSAR plots gave insights into the structure–activity relationship of these compounds, which may aid in the design of potent benzopyrrole derivatives as anticonvulsant agents. So, our research can make a great impact on those medicinal chemists who work on the development of anticonvulsant agents.

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Design, Synthesis, Pharmacological Evaluation and Molecular Docking Studies of Substituted Oxadiazolyl-2-Oxoindolinylidene Propane Hydrazide Derivatives

Cited by 13 publications

References 12 publications

Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

Hybrid organic molecules as antiinflammatory agents; a review of structural features and biological activity

Development of novel indole‐linked pyrazoles as anticonvulsant agents: A molecular hybridization approach

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