Phthalazines and phthalazine hybrids as antimicrobial agents: Synthesis and biological evaluation

Abstract

Phthalazine and phthalazinone derivatives are important owing to their significant biological activities and pharmacological properties. Herein, a benzoic acid derivative (2), a benzoxazin-1-one derivative (3), and an oxophthalazin-2(1 H)-yl)acetohydrazide (13) are utilized as precursors to construct a novel series of phthalazinones bearing various valuable functional groups in excellent yields via several simple and promising approaches. Finally, the antimicrobial activity of the newly synthesized phthalazines is screened against different microbial strains; namely, Gram-negative and Gram-positive bacteria utilizing Amoxicillin as a standard drug.

Microwave‐Assisted Synthesis of Phthalazinone Derivatives with Biological Activity and In Silico Antiproliferative Studies

“…Preparation of 2-(4-isopropyl-benzoyl)-benzoic acid 1, via Friedel-Crafts acylation of phthalic anhydride, and cumene in the presence of AlCl 3 anhydrous by the reported procedure. [10,42,43] In addition, phthalazinone derivatives 2-12, were prepared through a cyclocondensation reaction between an acid 1 and the presence of hydrazine hydrate, phenylhydrazine, 3-nitrophenyl hydrazine hydrochloride, 2,4-dinitrophenyl hydrazine, 2-thiophene carboxylic hydrazide, 2-furoic acid hydrazide, semicarbazide, thiosemicarbazide, 4-chlorophenyl hydrazine hydrochloride, 2,4-dimethylphenyl hydrazine, and benzoyl hydrazine in ethanol as solvent, the reactions are carried out by two procedures: the first is a conventional method, according to the reaction mixture is refluxed using thermal heat at 60-70 °C under nitrogen air for 6hr; the reaction mixture is left for 24hr at 25 °C, then worked up. Otherwise, the second procedure, which is accomplished by using MW assisted where the reaction mixture is left overnight at RT, then precipitates filtered off, then washed with cold ethanol to give compounds 2-12 respectively, is shown in (Scheme 1).…”

Design, synthesis, and exploration of antibacterial activity of 6H-1,2-oxazin-6-ones

“…[3][4][5][6] Grignard reagents, metal catalysts, phosphorus compounds, and reactions involving nitro compounds have been useful options in synthesizing these heterocycles. [7][8][9][10][11][12][13][14][15][16][17][18][19][20] While these processes offer different synthesis variants, most have disadvantages, such as numerous reaction steps, expensive reagents, the use of metallic catalysts and bases, long reaction times, and yields ranging from low to moderate. 3,[7][8][9][10][11][12][13][14][15][16][17][18][19][20] 6H-1,2-Oxazin-6-ones showed a wide range of biological properties, including modulation of glucocorticoid receptors, anticancer, antifungal, and antibacterial activities.…”

Synthesis and Antimicrobial Activity of New Heteroaryl(aryl) Thiazole Derivatives Molecular Docking Studies

“…Phtalazino derivatives are also mentioned as antimicrobial agents [ 38 , 39 , 40 ]. On the other hand, sulfonamides have attracted the interest of researchers due to their wide spectrum of biological activities, including dihydrofolate reductase (DHFR) inhibitors [ 41 ], antitumor [ 42 , 43 ], carbonic anhydrase inhibitors [ 44 , 45 ], anti-inflammatory [ 46 ], antiretroviral activity [ 47 , 48 ], antimicrobial [ 49 , 50 ], and others [ 51 , 52 , 53 ].…”