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

Abstract

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.

Design, synthesis, molecular docking and DFT studies on novel melatonin and isatin based azole derivatives

“…1 H -indole-2,3-dione, which is commonly referred to as Isatin or indenedione, is a versatile moiety with a broad range of biological activity. Isatin is the precursor for a number of derivatives that possess a broad range of potential biological and pharmaceutical properties 23 such as anticancer properties in various types of cancers, 24–26 antibiotics, 27 anxiogenic, 28 antibacterial, 29 antidiabetic, 30 anticonvulsant, 31 sedative, 32 carboxylesterases, 33 antidepressants, 34 antifungals, 35 antimicrobial 36 etc. Triazoles, namely 1,2,3-triazole and 1,2,4-triazole, are among the most significant groups of nitrogen-containing heterocycles.…”

Isatin derivatives as broad-spectrum antiviral agents: the current landscape

“…In another work, a series of N -substituted 5-carboxamide-isatin derivatives [ 16 ] (Fig. 20 ) was designed by Zhou and his coworkers as potential SARS-COV 3C-like protease inhibitors [ 55 ].…”

“…Isatin (1 H -indole-2,3-dione) (Fig. 1 ) is a privileged heterocyclic motif with a broad spectrum of biodynamic activities, such as anticancer [ 10 ], antitubercular [ 11 , 12 ] antimalarial [ 13 , 14 ] antibacterial [ 15 ] anticonvulsant [ 16 ] and antiviral [ 17 , 18 ] activities. In addition, clinically successful isatin-based drugs, such as sunitinib, semaxanib and toceranib (Fig.…”

Development of Isatin‐Based Schiff Bases Targeting VEGFR‐2 Inhibition: Synthesis, Characterization, Antiproliferative Properties, and QSAR Studies

“…In the continuous effort of our research group to develop potential drug candidates for cancer, [20,21] we utilized the isatin scaffold to synthesize various Schiff bases. Isatin-based Schiff bases are reported for diverse pharmacological properties such as analgesic, [22,23] anti-inflammatory, [24][25][26] antimicrobial, [27][28][29] antioxidant, [30][31][32][33] anticonvulsant, [34][35][36] and most predominantly, anticancer [37][38][39][40] properties. In addition, reported studies of isatin Schiff bases as VEGFR-2 inhibitors are encouraging.…”