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

Ibrahim, Musab Mohamed; Elsaman, Tilal; Al-Nour, Mosab Yahya

doi:10.1155/2018/9139786

Cited by 15 publications

(18 citation statements)

References 24 publications

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“…Furthermore, the lead finder program [69] on Cresset flare software [23] is characterized by the combination between the genetic algorithm and different optimization strategies leading to great efficiency, robustness, accuracy, and speed of calculations [69]. Musab Ibrahim et al [77] found the results of a molecular docking study about novel synthesized COX enzyme inhibitors conducted in Cresset Flare software were aligned with results of the conducted in vivo study. Depending on that, the obtained results of the predicted targets could be with considerable accuracy.…”

Section: -D-alanine D-alanine Ligase Enzymementioning

confidence: 99%

Ellagic Acid, Kaempferol, and Quercetin from Acacia nilotica: Promising Combined Drug With Multiple Mechanisms of Action

2019

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The pharmacological activity of Acacia nilotica's phytochemical constituents was confirmed with evidence-based studies, but the determination of exact targets that they bind and the mechanism of action were not done; consequently, we aim to identify the exact targets that are responsible for the pharmacological activity via the computational methods. Furthermore, we aim to predict the pharmacokinetics (ADME) properties and the safety profile in order to identify the best drug candidates. To achieve those goals, various computational methods were used including the ligand-based virtual screening and molecular docking. Moreover, pkCSM and SwissADME web servers were used for the prediction of pharmacokinetics and safety. The total number of the investigated compounds and targets was 25 and 61, respectively. According to the results, the pharmacological activity was attributed to the interaction with essential targets. Ellagic acid, Kaempferol, and Quercetin were the best A. nilotica's phytochemical constituents that contribute to the therapeutic activities, were non-toxic as well as non-carcinogen. The administration of Ellagic acid, Kaempferol, and Quercetin as combined drug via the novel drug delivery systems will be a valuable therapeutic choice for the treatment of recent diseases attacking the public health including cancer, multidrug-resistant bacterial infections, diabetes mellitus, and chronic inflammatory systemic disease.

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Section: -D-alanine D-alanine Ligase Enzymementioning

confidence: 99%

Ellagic Acid, Kaempferol, and Quercetin from Acacia nilotica: Promising Combined Drug With Multiple Mechanisms of Action

2019

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“…Initially, adamantane-1-carboxylic acid (9) was subjected to esterification (Scheme 1) to afford methyl adamantane-1-carboxylate (10) in good yield (85%). Subsequent reaction of 10 with hydrazine hydrate under reflux condition (Scheme 1) provided adamantane-1-carbohydrazide (11) in excellent yield (98%) [27,28]. e 5-substituted isatin derivatives 12-14 are commercially available, while the key intermediates 15 and 16 were yielded by treatment of 12 and 13 with 37% formalin under reflux conditions and were obtained in 50% yield [29].…”

Section: Resultsmentioning

confidence: 99%

“…On the contrary, intermediate 17 (62%) was derivatized through alkylation of 5-bromoisatin (13) with benzyl chloride in DMF at 80°C using catalytic amount of potassium carbonate [29]. Finally, the designed Schiff bases (18-23) (47-82%) were prepared following the synthetic route depicted in Scheme 2 via condensation of adamantane-1-carbohydrazide (11) with the appropriate isatin derivative (12)(13)(14)(15)(16)(17) according to a reported procedure [11].…”

Section: Resultsmentioning

confidence: 99%

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Schiff Bases of Isatin and Adamantane-1-Carbohydrazide: Synthesis, Characterization and Anticonvulsant Activity

Osman

Elsaman

Yousef

et al. 2021

Journal of Chemistry

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Epilepsy is the most common neurological condition and cause of substantial morbidity and mortality. In the present study, the molecular hybridization tool was adopted to obtain six Schiff bases of isatin and adamantane-1-carbohydrazide (18–23). Then, their anticonvulsant activity was evaluated using pentylenetetrazole- (PTZ-) induced seizure model using phenobarbitone as a positive control. Our findings showed that compounds 18–23 provided significant protection against PTZ-induced seizure, and maximum activities were associated with compound 23. Moreover, all investigated compounds increased the latency of induced convulsion and reduced the duration of epilepsy with compound 23 being the best. Interestingly, most of the synthesized molecules showed reduction in neurological symptoms and severity of the seizure. Molecular docking studies suggest GABA-A receptor as a potential target, and in silico ADME screening revealed that the pharmaceutical properties of compound 23 are within the specified limit. Thus, compound 23 was identified as a promising candidate that warrants further drug discovery processes.

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“…It has been shown that isatin derivatives, which possess electron withdrawing groups such as halogens, at the C5 or C7 position exhibit remarkable anti-inflammatory activity (23,24). Thus, it is also possible to suggest that the anti-inflammatory activity of COPHCT may be attributed to the presence of the chlorine in C5 position in the structure.…”

Section: Discussionmentioning

confidence: 99%

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

Dantas

Fonseca

Pereira

et al. 2020

Braz J Med Biol Res

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Several isatin derivatives have shown important biological activities, which have attracted interest from researchers. For this reason, the present study aimed to evaluate the anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide (COPHCT) in mice. Three doses of this compound were tested: 1.0, 2.5, and 5.0 mg/kg. The anti-inflammatory activity was assessed using the carrageenan-induced paw edema model and the zymosan-induced air pouch model. The evaluation of the antinociceptive effect was performed through the formalin test and the acetic acid-induced abdominal writhing test. The paw edema assay demonstrated that all doses of the compound showed a significant reduction of the edema in the second hour evaluated, but a better response was observed in the fourth hour. The zymosan-induced air pouch model indicated that the compound, in all doses, significantly reduced leukocyte migration and total protein concentration levels. In the formalin test, the doses 1.0, 2.5, and 5.0 mg/kg of COPHCT showed activity only in the second phase, with reduction in paw pain time of 73.61, 79.46, and 73.85%, respectively. The number of abdominal writhings decreased with the increasing dose, but only 5.0 mg/kg COPHCT exhibited a significant response, with a reduction of 24.88%. These results demonstrated the ability of this compound to interfere in the anti-inflammatory activity of edema, vascular permeability, and cell migration. In addition, its possible antinociceptive effect may be related to the dose used.

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

Cited by 15 publications

References 24 publications

Ellagic Acid, Kaempferol, and Quercetin from Acacia nilotica: Promising Combined Drug With Multiple Mechanisms of Action

Ellagic Acid, Kaempferol, and Quercetin from Acacia nilotica: Promising Combined Drug With Multiple Mechanisms of Action

Schiff Bases of Isatin and Adamantane-1-Carbohydrazide: Synthesis, Characterization and Anticonvulsant Activity

Anti-inflammatory and antinociceptive effects of the isatin derivative (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)-N-phenyl-hydrazinecarbothioamide in mice

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