Amide derivatives of [6-acyl-2-benzothiazolinon-3-yl] acetic acids as potential analgesic and anti-inflammatory compounds

Önkol, Tijen; Banoğlu, Erden; Dündar, Yasemin; Küpeli, Esra; Şahi̇n, Mustafa

doi:10.1007/s00044-009-9168-x

Cited by 11 publications

(6 citation statements)

References 23 publications

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“…Amides have been shown to possess an important pharmacophoric spectrum of wider biological activities. [38][39][40] Design and the synthesis of dihydropyridine derivatives with amide groups at the C3, C5 positions of DHP, which are important pharmacophores, have been planned. Many of the compounds previously reported exhibit both antiinflammatory and analgesic activities and hence were selected as target molecules for this in vivo analgesic studies.…”

Section: Introductionmentioning

confidence: 99%

Design of 1,4-Dihydropyridine Hybrid Benzamide Derivatives: Synthesis and Evaluation of Analgesic Activity and Their Molecular Docking Studies

Idhayadhulla¹,

Surendrakumar²,

Meenakshisundaram³

et al. 2022

DDDT

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This study aims to determine the analgesic activity of 1,4-dihydropyridine hybrid benzamide derivatives. These hybrid derivatives were synthesized, and their analgesic activity was studied. The synthesis method applied was a one-step reaction involving a green chemistry approach. Methods: The compounds were prepared via the amination method with a yield ranging between 82% and 93%. The title compounds were confirmed by means of IR, 1 H and 13 C NMR, and mass spectral analyses. The pharmacological activity of all the synthesized compounds was evaluated, and the analgesic activities were monitored in vivo (by tail immersion methods), with a digital analgesiometer. The drug response and damage of tail ata concentration of 10 mg/kg were measured by tail-flicking latency. Results: The activity of compound 2c (81.35% activity at 5mg/kg) can be correlated with its salicylamidemoiety (13.99% activity at 5mg/kg), and diclofenac showed comparable activity (79.21% activity at 5mg/kg reference drugs). Compound 2c has a higher potential to inhibit COX proteins compared to diclofenac. The drug-like nature of the molecule 2c corresponds to its ADME properties. Conclusion:In this study, all the synthesized compounds were found to possess significant analgesic activities; particularly, the performance of compound 2c is excellent. Thus, the preparative method described is an apt route for developing novel therapeutic formulations.

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Section: Introductionmentioning

confidence: 99%

Design of 1,4-Dihydropyridine Hybrid Benzamide Derivatives: Synthesis and Evaluation of Analgesic Activity and Their Molecular Docking Studies

Idhayadhulla¹,

Surendrakumar²,

Meenakshisundaram³

et al. 2022

DDDT

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“…14 The character of substituents at the 2-or 3-position of the indole nucleus of isatin has been shown to significantly regulate their anti-inflammatory and anti-bacterial activities. [15][16][17][18][19] Ramana H. et al 20 synthesized a series of the compounds 3-(substituted hydrazone)-1H benzoindol-2(3H)-one derivative. All synthesized compounds were evaluated for antibacterial activity by using the agar diffusion method.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of New Isatin-Ibuprofen Derivatives with Expected Biological Activity

H.¹,

H.²,

H.³

2022

IJDDT

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Ibuprofen is one of the most important members of NSAIDs, named aryl propionic acid derivative. Isatin (1H-indole-2,3-dione) is an important molecule of heterocyclic compounds that have many biological activities. This work illustrates the synthesis of new ibuprofen-isatin derivatives by connecting ibuprofen hydrazide with different isatin derivatives by a condensation reaction, followed by characterization by fourier-transform infrared spectroscopy (FTIR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy. The anti-inflammatory activity was evaluated by using the egg-white induce edema method for all the synthesized compounds (5-8), the compounds 5 and 6 showed better anti-inflammatory activity than ibuprofen as a standard compound. Their antimicrobial activity was evaluated and compared with ciprofloxacin, ampicillin, and fluconazole; the compounds 5 and 7 have moderate antibacterial activity against gram-positive and gram-negative bacteria, with lower antifungal activity.

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“…Comprehensive literature survey revealed that Isatin moiety possesses diverse pharmacological activities including anti-inflammatory activity [9–11]. Further, it has been reported that the substituents at the 2- or 3-position of the indole nucleus are closely related to their anti-inflammatory properties [12–14]. The size of active site in cyclooxygenase enzyme COX-2 is larger than cyclooxygenase enzyme COX-1; hence the extension in ligand size may increase the selectivity toward COX-2 enzyme [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Anti-Inflammatory Activity, and In Silico Study of Novel Diclofenac and Isatin Conjugates

Ibrahim

Elsaman

Al-Nour

2018

International Journal of Medicinal Chemistry

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The design, synthesis, and development of novel non-steroidal anti-inflammatory drugs (NSAIDs) with better activity and lower side effects are respectable area of research. Novel Diclofenac Schiff's bases (M1, M2, M4, M7, and M8) were designed and synthesized, and their respective chemical structures were deduced using various spectral tools (IR, 1H NMR, 13C NMR, and MS). The compounds were synthesized via Schiff's condensation reaction and their anti-inflammatory activity was investigated applying the Carrageenan-induced paw edema model against Diclofenac as positive control. Percentage inhibition of edema indicated that all compounds were exhibiting a comparable anti-inflammatory activity as Diclofenac. Moreover, the anti-inflammatory activity was supported via virtual screening using molecular docking study. Interestingly compound M2 showed the highest in vivo activity (61.32% inhibition) when compared to standard Diclofenac (51.36% inhibition) as well as the best binding energy score (-10.765) and the virtual screening docking score (-12.142).

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Amide derivatives of [6-acyl-2-benzothiazolinon-3-yl] acetic acids as potential analgesic and anti-inflammatory compounds

Cited by 11 publications

References 23 publications

Design of 1,4-Dihydropyridine Hybrid Benzamide Derivatives: Synthesis and Evaluation of Analgesic Activity and Their Molecular Docking Studies

Design of 1,4-Dihydropyridine Hybrid Benzamide Derivatives: Synthesis and Evaluation of Analgesic Activity and Their Molecular Docking Studies

Synthesis, Characterization of New Isatin-Ibuprofen Derivatives with Expected Biological Activity

Synthesis, Anti-Inflammatory Activity, and In Silico Study of Novel Diclofenac and Isatin Conjugates

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