Uses of 2-Ethoxy-4(3H) quinazolinone in Synthesis of Quinazoline and Quinazolinone Derivatives of Antimicrobial Activity: The Solvent Effect

Abstract

2-Ethoxy-4(3H) quinazolinone 1 was synthesized and allowed to react with various halides, namely: alkyl, benzyl, allyl, acyl, haloacetyl, crotonyl, benzoyl, 2-furoyl and 1-naphthalenesulphonyl halides affording quinazoline and quinazolinone derivatives. The reactions of compound 1 with phosphorus oxychloride, phosphorus pentasulfide, ethyl chloroformate, ethyl chloroacetate, α-bromoglucose tetraacetate, p-acylaminobenzenesulfonyl chloride, acrylonitrile, chalcone and chalcone oxide were also investigated. Depending on the reaction condition and reactant halide, the type of substituent (alkyl, acyl, aroyl, etc.) that will reside on either of the expected positions (3 or 4) on the quinazoline moiety can control the reaction pathway for synthesis of the promising products. The significant role of solvent responsible for determining both the reaction pathway and type of products synthesized was also discussed. Some derivatives were chosen for biological screening test against Gram (-ive) and Gram (+ive) bacteria and two strains of fungi.

Microwave‐ultrasonic assisted synthesis, and characterization of novel 3′‐(amino, hydrazino and hydrazide)‐6′‐bromo‐spiro(isobenzofuran‐1,2′‐quinazoline)‐3,4′‐dione derivatives as antimicrobial agents

“…Quinazolinones and quinazolines are noteworthy in medicinal chemistry [1,2], quinazolinone nucleus stability pushed a lot of researchers to introduce many bioactive moieties to this nucleus to produce new potential medicinal agents [3]. From a literature survey, the quinazolin-4 (3H)-one derivatives are of interest because of their wide biological activities [4][5][6][7][8][9][10][11][12][13] carrying antimicrobial sites as considered a wide array of pharmaceutical properties [14][15][16][17][18][19][20][21][22][23]. Moreover, quinazolinones are considered the most important component of most natural alkaloids in some families of plants, animal, and microorganisms [24].…”

Design, Regiospecific Green Synthesis, Chemical Computational Analysis, and Antimicrobial Evaluation of Novel Phthalazine Heterocycles

“…It also acts as a center structure for different bioactive molecules because of its easy fictionalization at different substitution patterns and their roles as pharmacophore . Some of O ‐alkyl‐phthalazine derivatives were monitored in vitro for their antimicrobial effect, and the energy variance between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) plays a significant role in the electronic studies of these molecules by quantum chemical calculations that reflects the relation between delocalization, electron distribution, and chemical reactivity with kinetic stability of the compound . Phthalazine derivatives were announced to acquire anticonvulsant , antitumor , antihypertensive, antithrombotic , antidiabetic , antitrypanosomal , anti‐inflammatory , cardiotonic , and vasorelaxant activities.…”

Nucleosides 8 [18]: Ribosylation of Fused Quinazolines—Synthesis of New [1,2,4]Triazolo[5,1‐b]‐ and [1,2,4]Triazino[3,2‐b]quinazoline Nucleosides of Fluorescence Interest

“…In recent years there has been an increasing interest in the chemistry of 4(3H)-quinazolinones because of their biological importance. Many of them show antifungal, antibacterial, anticancer, anti-inflammatory, anticonvulsant, immunotropic, hypolipidemic, antitumor, antiulcer, analgesic, antiproliferative activities and inhibitory effects of thymidylate synthase and poly(ADP-ribose) polymerase (PARP) [9].…”