Design, Synthesis and Preliminary Pharmacological Evaluation of New Non-Steroidal Anti-Inflammatory Agents Having a 4-(Methylsulfonyl) Aniline Pharmacophore

Mahdi, Monther F.; Mohammed, Mohammed Hassan; Jassim, Akeel Abdul Kadhum

doi:10.3390/molecules17021751

Cited by 15 publications

(9 citation statements)

References 24 publications

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“…As shown in Figure 2(b), injection of 100 μ L 10% fresh egg white noticeably elicited induced acute inflammatory model and the inflammatory symptom-paw edema peak at 0.5–1 h after injection then gradually relieved but persisted for 4 h [23]. Pretreatment with the denatured NNAV (90, 270 μ g/kg), native NNAV(90 μ g/kg), and TWP (15 mg/kg) all significantly reduced paw edema at 1 h after injection of egg white, when compared to the saline group.…”

Section: Resultsmentioning

confidence: 99%

Antinociceptive and Anti-Inflammatory Effects of Orally Administrated Denatured Naja Naja Atra Venom on Murine Rheumatoid Arthritis Models

Zhu

et al. 2013

Evidence-Based Complementary and Alternative Medicine

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To investigate the antinociceptive and anti-inflammatory activities of the denatured Naja Naja atra venom (NNAV) in rheumatoid arthritis-associated models, the denatured NNAV (heat treated; 30, 90, 270 μg/kg), the native NNAV (untreated with heat; 90 μg/kg), and Tripterygium wilfordii polyglycoside (TWP, 15 mg/kg) were administrated orally either prophylactically or therapeutically. We measured time of licking the affected paw in formaldehyde-induced inflammatory model, paw volume in egg-white-induced inflammation, and granuloma weight in formalin-soaked filter paper-induced granuloma. For adjuvant-induced arthritis (AIA) rats, paw edema, mechanical withdrawal threshold, serum levels of TNF-α and IL-10, and histopathological changes of the affected paw were assessed. We found that the denatured NNAV (90, 270 μg/kg) significantly reduced time of licking paw, paw volume, and granuloma weight in above inflammatory models and also attenuated paw edema, mechanical hyperalgesia, and histopathology changes in AIA rats. Additionally, the increase in serum TNF-α and the decrease in serum IL-10 in AIA rats were reversed by the denatured NNAV. Although the native NNAV and TWP rendered the similar pharmacological actions on the above four models with less potency than that of the denatured NNAV, these findings demonstrate that oral administration of the denatured NNAV produces antinociceptive and anti-inflammatory activities on rheumatoid arthritis.

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Section: Resultsmentioning

confidence: 99%

Antinociceptive and Anti-Inflammatory Effects of Orally Administrated Denatured Naja Naja Atra Venom on Murine Rheumatoid Arthritis Models

Zhu

et al. 2013

Evidence-Based Complementary and Alternative Medicine

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“…After 4 hr exposure to 80% human plasma, naproxen prodrug 169 displayed 87.23% of metabolic hydrolysis. Continuing their efforts in search of potent and safer NSAIDs, Mahdi et al further synthesized a new series of NSAID (naproxen, indomethacine, diclofenac and mefanamic acid) derivatives bearing 4‐(methylsulfonyl)aniline pharmacophore . From the set of compounds evaluated in the egg‐white induced rat paw edema assay, naproxen–4‐methylsulfonylanilne conjugate ( 170 ) displayed the highest potency with activity greater than the clinically used drug diclofenac.…”

Section: Development Of Various Nsaids and Their Derivativesmentioning

confidence: 99%

Recent Developments in Chimeric NSAIDs as Safer Anti‐Inflammatory Agents

Kumar

Sharma

2014

Medicinal Research Reviews

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NSAIDs are among the most widely prescribed medications across the world, but the gastrointestinal (GI) toxicity still remains the biggest problem and the challenge for current NSAIDs-based therapeutics. The development of selective COX-2 inhibitors was driven by the assumption that selective inhibition of COX-2 would reduce the GI side effects. However, the initial enthusiasm for selective COX-2 inhibitors has faded away due to the emergence of serious side effects associated with the long-term use of these NSAIDs. In the recent years, a number of novel approaches to develop gastrosparing NSAIDs have been explored with the promising results. This review deals with such approaches and strategies that have been employed in the last two decades and are being used currently in the design and development of safer NSAIDs.

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“…(dissolved in dimethyl sulfoxide 10% v/v). (20) Dose of reference compound /Mwt. of reference compound = dose of tested compound/ Mwt.…”

Section: Methods Animalsmentioning

confidence: 99%

Synthesis, Characterization and Acute Anti-inflammatory Evaluation of New Mefenamic Acid Derivatives Having 4-Thiazolidinone Nucleus

Alsafi

Farhan²

2019

IJPS

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Mefenamic acid (MA) is one of the non-steroidal anti-inflammatory drugs, it is widely used probably due to having both anti-inflammatory and analgesic activity, the main side effects of mefenamic acid include gastrointestinal tract (GIT) disturbance mainly diarrhea, peptic ulceration, and gastric bleeding. The analgesic effects of NSAIDs are probably linked to COX-2 inhibition, while COX-1 inhibition is the major cause of this classic adverse effects. Introduction of thiazolidinone may lead to the increase in the bulkiness leads to the preferential inhibition of COX-2 rather than COX-1 enzyme. The study aimed to synthesize derivatives of mefenamic acid with more potency and to decrease the drug's potential side effects, new series of 4-thiazolidinone derivatives of mefenamic acid were synthesized IVa-g. The synthetic procedures for target compounds and their intermediates are designed to be as follows: acylation of secondary amine of mefenamic acid by chloroacetylchloride to produce compound (I), then reaction between compound (I) and hydrazine hydrate to form hydrazine derivative of mefenamic acid (compound II). After that, Schiff base formation by addition of seven benzaldehyde derivatives and finally, cyclization in presence of thioglycolic acid to form 4-thiazolidinone heterocyclic ring. The characterization of the titled compounds has been established on the basis of their spectral FTIR, 1 HNMR data, and by measurements of their physical properties. In vivo acute anti-inflammatory effect of the synthesized compounds was evaluated in rats using egg-white induced edema model of inflammation. The tested compounds and the reference drug produced significant reduction of paw edema with respect to the effect of dimethyl sulfoxide 10%v/v (control group). Compound IVe showed more potent effect than mefenamic acid at 240-300 min, while at time 300 min, compounds IVa and IVd exhibit more potent anti-inflammatory effect than mefenamic acid (50mg/kg, i.p.) as they reduced paw edema significantly more than mefenamic acid at mentioned intervals (p<0.05) . On the other hand compound IVc exhibited lower anti-inflammatory effect.

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Design, Synthesis and Preliminary Pharmacological Evaluation of New Non-Steroidal Anti-Inflammatory Agents Having a 4-(Methylsulfonyl) Aniline Pharmacophore

Cited by 15 publications

References 24 publications

Antinociceptive and Anti-Inflammatory Effects of Orally Administrated Denatured Naja Naja Atra Venom on Murine Rheumatoid Arthritis Models

Antinociceptive and Anti-Inflammatory Effects of Orally Administrated Denatured Naja Naja Atra Venom on Murine Rheumatoid Arthritis Models

Recent Developments in Chimeric NSAIDs as Safer Anti‐Inflammatory Agents

Synthesis, Characterization and Acute Anti-inflammatory Evaluation of New Mefenamic Acid Derivatives Having 4-Thiazolidinone Nucleus

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