Expeditious synthesis and biological evaluation of pyrazole conjugated selenium Lumefantrine analogues

• Published in: Journal of the Iranian Chemical Society Vol. 20; no. 8; pp. 1903 - 1916
• Main Authors: Puthran, Divyaraj, Kamat, Vinuta, Purushotham, Nikil, Poojary, Boja, Rasheed, Mohammed Shafeeulla, Hegde, Hemant
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.08.2023; Springer Nature B.V
• Subjects: Analytical Chemistry; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Fungicides; Inorganic Chemistry; Microorganisms; Molecular docking; Organic Chemistry; Original Paper; Physical Chemistry; Pyrazole; Selenium; Spectral methods; Toxicity testing; Vilsmeier-Haack reaction; 1,3-Diarylpyrazole-4-carboxaldehydes; Vilsmeier–Haack reaction; Anti-inflammatory; Molecular docking
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-023-02807-9

This study describes the synthesis and characterization of some 1-(2,7-dichloro-9-[(1,3-diphenyl-1 H -pyrazol-4-yl)methylene]-9 H -fluoren-4-yl)-2-(methylselenyl)-ethanols and their biological evaluation as antimicrobial agents. The synthesis of the target compounds requires two key starting materials, 1-[2,7-dichloro-9 H -fluoren-4-yl]-2-(methylselanyl)ethan-1-ol and various 1,3-diarylpyrazole-4-carboxaldehydes. The key intermediates, 1,3-diarylpyrazole-4-carboxaldehydes were prepared by the Vilsmeier-Haack reaction. Finally, the target compounds were obtained by a simple Knoevenagel condensation. The structures of the newly synthesized compounds were established based on spectral techniques. The synthesized compounds were screened for their in vitro antibacterial, antifungal, and anti-inflammatory activities. All the compounds were tested for their preliminary cytotoxicity by hemolysis assay. The microbial growth inhibition was also investigated via in silico molecular docking studies. Graphical abstract