Synthesis, characterization and evaluation of antidengue activity of enantiomeric Schiff bases derived from S-substituted dithiocarbazate

Abstract

A series of Schiff bases have been successfully synthesized through the acid-catalyzed condensation of S-substituted dithiocarbazates and three enantiomerically pure monoterpenes, (1R)-(+)-camphor, (1S)-(-)-camphor, (1R)-(-)-camphorquinone, (1S)- (+)-camphorquinone, (R)-(-)-carvone and (S)-(+)-carvone. Spectroscopic results revealed that the Schiff bases containing camphor or carvone likely adopted an E-configuration along the characteristic imine bond while those containing camphorquinone assumed a Z-configuration. The antidengue potential of these compounds was evaluated based on DENV 2 caused cytopathic effect (CPE) reduction-based in vitro evaluation. The compounds were validated through secondary foci forming unit reduction assay (FFURA). Compounds were also tested for their cytotoxicity against Vero cells. The compounds showed variable degrees of antiviral activity with the camphor compounds displaying the highest antidengue potential. The enantiomers of the compounds behaved almost similarly during the antiviral evaluation.

Schiff Base as Multifaceted Bioactive Core

“…In case of viral disorder, in the market there are numbers of drugs, but they are not fully active due to mutations in viruses. To overcome these problems, Schiff base derivatives are synthesized as an antiviral agent [82]. Different biological activities of Schiff bases are shown in Table 2.…”

A Series of Non-Oxido VIVComplexes of Dibasic ONS Donor Ligands: Solution Stability, Chemical Transformations, Protein Interactions, and Antiproliferative Activity

“…Over the last years, the interest in the study of ONS donor ligands has increased significantly due to their ligation properties and potential applications of their transition metal complexes in pharmacology and medicine. ,− For example, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, well known as triapine, is one of the most extensively studied drugs and has been tested in nearly 30 clinical phases I/II trials as an antiproliferative agent . Likewise, di-2-pyridylketone-4-cyclohexyl-4-methyl-3-thiosemicarbazone (DpC-TSC) has also entered clinical phase I studies as a chemotherapeutic agent. , Out of this class of compounds, similar to thiosemicarbazones, S-substituted dithiocarbazates (DTCs) are also well known for their antitumor, antimicrobial, antifungal, and antibacterial activities. ,− ,,, Moreover, N ’-(phenyl-pyridin-2-yl-methylene)-hydrazine carbodithioic acid methyl ester (PHCM) was also found to enhance radiation-induced cell death of an NSCLC cell line, H460, both in vivo and in vitro . Interestingly, the possible use in bio-imaging and in the treatment of pancreatic cancer of a dithiocarbazate-copper complex has been recently published …”

“…83,84 Out of this class of compounds, similar to thiosemicarbazones, S-substituted dithiocarbazates (DTCs) are also well known for their antitumor, antimicrobial, antifungal, and antibacterial activities. 68,[71][72][73][74][75][76]79,80,85 Moreover, N'-(phenyl-pyridin-2-yl-methylene)-hydrazine carbodithioic acid methyl ester (PHCM) was also found to enhance radiation-induced cell death of an NSCLC cell line, H460, both in vivo and in vitro. Interestingly, the possible use in bioimaging and in the treatment of pancreatic cancer of a dithiocarbazate-copper complex has been recently published.…”

Dithiocarbazate–FeIII, −CoIII, −NiII, and −ZnII Complexes: Design, Synthesis, Structure, and Anticancer Evaluation

“…Dithiocarbazate Schiff-base derivatives, which have a general structure similar to hydrazone and thiosemicarbazone ligands, are emerging prospective ligands in medicinal chemistry due to their various pharmaceutical and biological activities, such as antiamoebic, anticancer, and antibacterial activities. − Moreover, the structural changes of dithiocarbazate derivatives significantly impact biological activity . As an important class of Schiff-base ligands, dithiocarbazate Schiff-base derivatives have hard nitrogen-donor and soft sulfur atoms.…”