Synthesis, Characterization and Anticancer Molecular Docking Studies of Phenothiazine Derivatives – A Green Chemical Approach

Venkatesan, K.; Kumar, K. M.; Sivakumar, A.

doi:10.1002/slct.202302613

Cited by 3 publications

(1 citation statement)

References 34 publications

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“…Docking studies: The Auto Dock Vina program was used to carry out the molecular docking [38,39] of the synthesized compounds. The RCSB protein data bank was used to obtain the crystal structures of the applied proteins [40].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

Md,

Domala

2024

ajc

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Present study establishes a novel synthetic route of N-acetylated derivatives of 5-(2-phenyl-1,8-naphthyridine-3-yl)-1,3,4-oxadiazole-2-amine (6a-j), which was achieved in four steps with good yields. 2-Amino nicotinaldehyde and ethyl 3-oxo-3-phenylpropanoate on refluxing with triethylamine in ethanol undergoes Friedlander synthesis to furnish ethyl 2-phenyl-1,8-naphthyridine-3-carboxylate, which further converted into 2-phenyl-1,8-naphthyridine-3-carbohydrazide by reacting with hydrazine hydrate upon reflux, followed by cyclization with cyanogen bromide in the presence of water and 1,4-dioxane with sodium bicarbonate to afford 5-(2-phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine (5). Compound 5 was acetylated using numerous symmetrical anhydrides to synthesize novel N-acetylated derivatives (6a-j). The IR, 1H, 13C NMR and mass spectral analysis were used to characterize the structure of synthetic compounds. The synthesized compounds were evaluated for their antimicrobial efficiency against bacteria (S. aureus and E. coli) using ampicillin as a standard reference and against fungi (C. albicans) using fluconazole as a standard reference. Compound 6e exhibited good antibacterial properties while compounds 6c and 6e had shown high antifungal activity, whereas remaining compounds shown moderate to weaker antimicrobial activity. The synthesized derivatives verified their docking strength against Mtb MurB (PDB ID: 5JZX) and showed significant docking activity, however, compound 6f (-10.98 kcal/mol) and compound 6b (-10.52 kcal/mol) had a strong binding affinity compared to the other synthesized compounds.

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Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

Md,

Domala

2024

ajc

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Design, Synthesis, Characterization, and Docking Studies of Some 3,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione Derivatives

Pogaku,

Pagadala,

Damera

et al. 2024

Russ J Gen Chem

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Exploring the Biological Relevance of Fused S-Heterocycle Phenothiazine Derivatives

Singh,

Kaunert,

Lal

et al. 2024

Advances in Bioinformatics and Biomedical Engineering

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Phenothiazine and its derivatives have attracted a noteworthy attention within the medicinal chemistry' domain ascribed to its varied pharmacological activities and possible medically-beneficial applications. Fused S-heterocycle Phenothiazine being the most promising derivatives among all has displayed and showcased promising results in numerous biological evaluations. Phenothiazines are one of the class of compounds categorized by tricyclic structure which is comprised of central thiazine ring merged with two benzene rings. Such central thiazine rings incorporate the presence of sulphur atoms which acts as a catalyst to undergo various substitutions on the benzene rings that eventually results in versatility of the phenothiazines. The chapter focuses on the holistic understanding of the biological relevance of fused s-heterocycle phenothiazine derivatives and would highlight and elucidate the potential of phenothiazine derivative's development as therapeutic agent.

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Synthesis, Characterization and Anticancer Molecular Docking Studies of Phenothiazine Derivatives – A Green Chemical Approach

Cited by 3 publications

References 34 publications

Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

Synthesis, Antimicrobial Activities and Molecular Docking Studies of New N-Acylated Derivatives of 5-(2-Phenyl-1,8-naphthyridin-3-yl)-1,3,4-oxadiazol-2-amine

Design, Synthesis, Characterization, and Docking Studies of Some 3,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione Derivatives

Exploring the Biological Relevance of Fused S-Heterocycle Phenothiazine Derivatives

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