55558-97-9Relevant academic research and scientific papers
Design, synthesis and biological evaluation of novel quinazoline-2,4-diones conjugated with different amino acids as potential chitin synthase inhibitors
Noureldin, Nada A.,Kothayer, Hend,Lashine, El-Sayed M.,Baraka, Mohamed M.,Huang, Yanrong,Li, Bing,Ji, Qinggang
, p. 560 - 569 (2018)
A series of (2-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl) acetamido) acids) (6 a-m), (7) has been designed to inhibit the action of fungus chitin synthase enzyme (CHS). The synthesis of the designed compounds was carried out in four steps starting from the reaction between 1-methylquinazoline-2,4(1H,3H)-dione and ethyl chloroacetate to yield the ethyl acetate derivative. This ester was hydrolyzed to the corresponding carboxylic acid derivative that was then utilized to couple several amino acids getting the final designed compounds. The synthesized compounds were tested for their inhibition against CHS. Compound 7 showed the highest potency among others with minimum inhibitory concentration (IC50) of 0.166 mmol/L, while polyoxin B (the positive control) had IC50 of 0.17 mmol/L. The synthesized compounds were also evaluated for their in vitro antifungal activity using Aspergillus fumigates, Aspergillus flavus, Crytococcus neoformans and Candida albicans. Unfortunately, the 14 synthesized compounds showed lower in vitro activity compared to the used active controls. However, compound 6m and fluconazole have synergistic effect on Aspergillus flavus; Compounds 7 and fluconazole have synergistic effects on Aspergillus fumigates.
Synthesis of some substituted quinazolinediones as potential inhibitors of smooth muscle contraction
Akgun,Hollstein,Hurwitz
, p. 735 - 739 (2007/10/02)
3-Substituted 2,4(1H,3H)-quinazolinediones were prepared from the corresponding N-substituted 2-aminobenzamides by treatment with ethyl chloroformate and KOH in ethanol. Also, a series of 3-substituted and 1-methyl-3-substituted 2,4(1H,3H)-quinazolinediones were synthesized by the reaction of 1-methyl-1,4-dihydro- and 1,4-dihydro-2,4-dioxo-3(2H)-quinazolineacetic acid with the corresponding N-substituted piperazines. The 13C NMR spectra and mass spectra of the compounds were measured and signals were assigned. Some of the compounds showed inhibitory action on contractile function of smooth muscle.
Quinazoline Carboxylic Acids, Part X. Synthesis of 1-Methyl-2,4-dioxo-quinazolin-3-yl-acetic Acid, 2,4-Dioxo-quinazolin-1-yl-acetic Acids, 2,4-Dioxo-1,3-quinazolinediacetic Acids and Their Esters
Suesse, Manfred,Johne, Siegfried
, p. 71 - 80 (2007/10/02)
2,4-Dioxo-quinazolin-1-yl-acetic acid esters (2) were prepared by the reaction of either 3,1-benzoxazine-2,4-diones (1) with urea in the melt or in solution or of the substituted anthranilic acid ester 4 with potassium cyanate in acid solution.The anthran
