Synthesis, Antimicrobial and Anti-inflammatory Activity of Some New Benzoxazinone and Quinazolinone Candidates

Abstract

Benzoxazinones and quinazolinones have a wide spectrum of biological activity. In this paper we focused on studying the antimicrobial and anti-inflammatory activities of some newly synthesized benzoxazinone and quinazolinone derivatives. Thus we prepared 2-[α-benzoylaminostyryl]-6,8-dibromo-3,1-benzoxazin-4(H)-one 2 which underwent a reaction with primary and secondary amines, and hydrazine hydrate to give compounds 3, 4 and 5, respectively. Treatment of 2 with hydroxylamine hydrochloride, formamide and/or NaN 3 / AcOH afforded compounds 7, 8, 11 and 12, respectively. Also, compound 2 reacted with maleic anhydride, aromatic hydrocarbons and/or active methylene compounds to produce compounds 13, 15a-c and 16, respectively. Most of the newly synthesized compounds showed significant antimicrobial and anti-inflammatory activities comparable to ampicillin, mycostatine and indomethacin positive controls.

Toxicity and Anti-promastigote Activity of Benzoxazinoid Analogs Against Leishmania (Viannia) braziliensis and Leishmania (Leishmania) infantum

“…ma-yuen, were able to reduce levels of histamine released from rat mast cells stimulated with concanavalin A and sensitized with immunoglobulin E. 28 In addition, benzoxazinone analogues, synthesized from N-(1-(6,8-dibromo-4-oxo-4H-benzo[d] [1,3]-oxazin-2yl)-2-phenylvinyl)benzamide, showed moderate to high anti-inflammatory activity in a carrageenan-induced rat paw edema model. 29 The anti-inflammatory effect of Bexderived compounds is of particular relevance because some forms of leishmaniasis, such as mucocutaneous, have a crucial inflammatory component pathophysiological component. 4 However, oral bioavailability, as well as the anti-inflammatory activity of the compounds employed in this study, have yet to be determined.…”

Crystal structure of 1,4-dihydro-1-phenylchromeno[4,3-c]pyrazole, C16H12N2O

“…On the other hand, chromene derivatives play important roles in biological and pharmacological activities such as antivascular, antitumor, antibacterial, antiin ammatory, and antimicrobial activities [2][3][4]. In our previous work, we report the synthesis and pharmacological activities of some other nitrogen-based heterocyclic derivatives as analgesic and anti-in ammatory [5][6][7], SARS-CoV 3C-like protease inhibitors [8], monoamino oxidase inhibitors [9], anticancer [10,11], and antimicrobial [12] agents. Recently, a series of azole, azolopyrimidine, and pyridopyrimidine derivatives containing chromanone moieties were reported [13].…”

Conventional and Microwave‐Assisted Synthesis and Biological Activity Study of Novel Heterocycles Containing Pyran Moiety

“…For the aforementioned importance and due to our interest in the synthesis of potentially bioactive heterocyclic compounds , we have prepared 2‐amino‐6‐(2,4‐dimethoxyphenyl)‐4‐(4‐methoxyphenyl)‐4 H ‐pyran‐3‐carbonitrile ( 1 ) via a new one‐pot four‐component methodology.…”