Design, Synthesis and Antibacterial Assessment of Active (4-Arylazo-3-Methyl-2-Thienyl) 4-Antipyrine Ketones.

Autor: Barakat KM; National Institute of Oceanography and Fisheries (NIOF), Kayet Bey, Elanfoushy, Alexandria, Egypt., Adel Elsayed S; National Institute of Oceanography and Fisheries (NIOF), Kayet Bey, Elanfoushy, Alexandria, Egypt., Yılmaz M; Osmaniye Korkut Ata University, Bahçe Vocational School, Department of Chemistry and Chemical Processing Technologies, Osmaniye, 80000, Türkiye., Abdel-Latif E; Department of Chemistry, Faculty of Science, Mansoura University, ET, 35516, Mansoura, Egypt., Etman HA; Department of Chemistry, Faculty of Science, Mansoura University, ET, 35516, Mansoura, Egypt., Hamed MA; National Institute of Oceanography and Fisheries (NIOF), Kayet Bey, Elanfoushy, Alexandria, Egypt., El Nemr A; National Institute of Oceanography and Fisheries (NIOF), Kayet Bey, Elanfoushy, Alexandria, Egypt.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Aug; Vol. 21 (8), pp. e202400894. Date of Electronic Publication: 2024 Jul 14.
DOI: 10.1002/cbdv.202400894
Abstrakt: The chemicals formed from antipyrines are flexible organic building blocks that are employed in the development of pharmaceuticals. By diazotizing (4-arylazo-3-hydroxy-2-thienyl) 4-antipyrine ketones 1a, 1b and 1c and (4-arylazo-3-methyl-2-thienyl) 4-antipyrine ketones (2a, 2b and 2c) further replaced with six other coupling components, a broad spectrum of hybrid molecules have been created. Mass spectra, NMR, FTIR, and elemental analyses have all been used to confirm the structures of the synthesised compounds. The antimicrobial screening was investigated by agar well diffusion and diluting the broth technique against both Gram-negative and positive-tested bacterial strains. (3-methyl-5-(phenylamino)-4-(4-tolylazo)-2-thienyl) 4-antipyrine ketone (2a) was found to be superior to Ciprofloxacin against test strains: Acinetobacter sp (34.33±1.15 mm), Listeria monocytogenes (29.33±1.15 mm) and Streptococcus sp. (19.33±1.15 mm). Also, good to moderate activities were expressed as minimum inhibitory concentration (MIC) and minimum bacterial concentration (MBC) which were recorded at 9±1 to 59.67±4.51 μg/mL and 16±4 to >512 μg/mL, respectively, using compounds 2a, 2b, and 2c. MBC/MIC ratio showed, that only, 2a and 2b have a bactericidal effect but other antipyrines with bacteriostatic strength. To conclude, it was suggested that the use of these novel synthesized (4-arylazo-3-methyl-2-thienyl) 4-antipyrine ketone derivatives molecules as a new chemical class of antimicrobial agents to perform new drug discovery in pharmaceutical preparations and medicinal research.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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