Synthesis, characterization, and screening for analgesic and anti-inflammatory activities of new 1,3,4-oxadiazole derivatives linked to quinazolin-4-one ring

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Sixteen Schiff bases of quinazolin‐4‐one‐linked 1,3,4‐oxadiazoles were synthesized by reaction with different aromatic aldehydes. Purity of newly synthesized derivatives was confirmed through thin‐layer chromatography, combustion analysis, and melting point. The structure of the derivatives was confirmed by determining infrared spectroscopy, nuclear magnetic resonance, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti‐inflammatory activities in mice and rats, respectively. In animal studies, the derivative (E)‐3‐(5‐(4‐(4‐methoxybenzylideneamino)phenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H)‐one showed more potent analgesic activity and the derivative (Z)‐3‐(5‐(2‐(2‐hydroxybenzylideneamino)phenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H)‐one showed more potent anti‐inflammatory activity as compared with other derivatives. The results of the present study indicate that reactions of 3‐(5‐(4‐aminophenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H)‐one and 3‐(5‐(2‐aminophenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H)‐one with different aromatic aldehydes produce Schiff bases of quinazolin‐4‐one‐linked 1,3,4‐oxadiazoles with potent analgesic and anti‐inflammatory activities.

Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis, Characterization, and Screening for Analgesic and Anti‐Inflammatory Activities of Schiff Bases of 1,3,4‐Oxadiazoles Linked With Quinazolin‐4‐One

Dewangan¹,

Nakhate²,

Verma³

et al. 2017

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“…Currently, the focus of researchers on the development of better, synergistic molecules by the hybridization of two or more active biomolecule or ligands is to develop newer derivative possessing good pharmacological activity . Triazole is an attractive bridge group, which could connect two pharmacophores to produce novel bifunctional molecules, while it is almost impossible to be hydrolyzed, oxidized, or reduced .…”

Section: Introductionmentioning

confidence: 99%

Analgesic and Anti‐inflammatory Potential of Merged Pharmacophore Containing 1,2,4‐triazoles and Substituted Benzyl Groups via Thio Linkage

Ahirwar¹,

Ahirwar²,

Lanjhiyana³

et al. 2018

A plethora of non‐steroidal anti‐inflammatory drugs are available in the market with adverse side effects like gastrointestinal irritation, bleeding, and ulceration. Currently, the focus of researcher on the development of better, synergistic molecules by the hybridization of two or more active biomolecule or ligands to develop newer derivative possessing good anti‐inflammatory activity with minimum side effects. In line with this, the present study was designed to synthesize a series of merged pharmacophore contaning1,2,4‐triazoles and substituted benzyl groups via thio linkage. Purity of the derivatives was confirmed by thin‐layer chromatography, combustion analysis, and melting point. Structure of these derivatives was set up by determining infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti‐inflammatory activities in mice and rats, respectively. In animal studies, the derivative 3‐(5‐(4‐nitrobenzylthio)‐4H‐1,2,4‐triazol‐3‐yl) pyridine showed more potent analgesic activity, and the derivative 3‐(5‐(2,4‐dimethylbenzylthio)‐4H‐1,2,4‐triazol‐3‐yl) pyridine showed more potent anti‐inflammatory activity as compared with other derivatives. The results of the present study indicate that reaction of pyridine linked 1,2,4‐triazole‐3‐thiol with different substituted benzyl halides to produce merged pharmacophore contaning1,2,4‐triazoles and substituted benzyl groups with potent analgesic and anti‐inflammatory activities. Docking studies were performed by using Argus lab, and all the derivatives exhibited good docking scores between −10 and −12 kcal/mol and were better as compared with standard drugs aspirin and indomethacin against cyclooxygenase‐2. Among all compounds, 3j has shown the maximum docking score and found in agreement to in pharmacological activities.

Synthesis and Molecular Docking Study of Novel Hybrids of 1,3,4‐Oxadiazoles and Quinoxaline as a Potential Analgesic and Anti‐Inflammatory Agents

Dewangan

Nakhate

Verma

et al. 2018

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in Wiley Online Library (wileyonlinelibrary.com).Novel hybrid molecules were synthesized through the amalgamation of quinoxaline residue with 1,3,4oxadiazole molecule. The purity of obtained 1,3,4-oxadiazoles derivatives containing quinoxaline residue (total 11) was confirmed through thin-layer chromatography, combustion analysis, and melting point, whereas their structures were confirmed by infrared spectroscopy, nuclear magnetic resonance, and mass spectroscopy. In animal studies, the derivatives 4-(5-(4-(3-methylquinoxalin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)benzenamine and 2-(5-(4-(3-methylquinoxalin-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)benzenamine showed excellent analgesic and anti-inflammatory activities, respectively, as compared with other derivatives. In order to rationalize the biological results of the derivatives, molecular docking studies were performed using Argus lab. The compounds exhibited good docking scores between À12.987 and À9.92 kcal/mol against cyclooxygenase-II (5IKQ) protein fragment.