Quinazolinone properties

Analytical Properties Resolution of transA, 2-diphenyloxirane, 2-methyl-3-(2 -methylphenyl)-4(3H)-quinazolinone, and some aromatic hydrocarbons Reference 9... 

Griffin RJ, et al. Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA 156. repair enzyme poly(ADP-ribose) polymerase (PARP). J. Med. 

In recent studies, 4(3H)-Quinazolinone derivatives have been reported to possess both antimicrobial and antiallergic properties [25], In a cell culture study, 6-Bromo-2-phenyl-3-[(4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl]-4(3H)-quinazolinone exhibited antiviral activity against VACV in E6SM cell culture at a concentration of 1.92 pg/mL. 

The pharmacokinetic properties for the quinazolinone diuretics are listed in Table 27.4. They have Although chlorothiazide has a duration of action of 6 to 12 ... 

Chlorthalidone has a long duration of action (48-72 hours) (see Table 27.3 for its other pharmacokinetic properties). Although quinethazone and metolazone are administered daily, chlorthalidone may be administered in doses of 25 to 100 mg three times a week. When chlorthalidone is formulated with the excipient povidone, the product. Thalitone. has greater bioavailability (>90%) and reaches peak plasma concentrations in a shorter time compared with its other products. Similar to the quinazolinones. it also is extensively bound to carbonic anhydrase in the erythrocytes. Chlorthalidone-induced effects on urine content and side effects are similar to those induced by thiazide diuretics. 

Independently, Zhou and co-workers used the same approach in their synthesis of highly functionalized quinazolines as potential anti-cancer therapeutics. In one example, fusion of 2-amino-3,4,5-trimethoxybenzoic acid with formamide under thermal conditions gave the desired quinazolinone in 25% yield. A dibenzofliran quinazoline derivative produced using this process exhibited anti-proliferative properties against several tumor types, including Bcap-37, PC3, A431, and BGC823 cell lines. 

Reid and co-workers prepared a number of napthanilic quinazolinones by condensing 3-amino-2-naphthoic acid with a fuiyl imidate in methanol under thermal conditions. The desired product, 2-(furan-2-yl)benzo[g]quinazolin-4(3//)-one, was produced in 43% yield. Compounds of this class have been shown to have effective anti-cancer and antibacterial properties. 

Larksarp and Alper used a palladium(II) catalyzed cyclocarbonylation reaction to generate a series of more complex and biologically relevant 4(3 0-Penicillium chrysogenum), have been shown to exhibit PTK inhibition and cholecystokinin inhibition as well as antimicrobial, anti-convulsant, anti-depressant and anti-inflammatory properties. Reaction of o-iodoaniline, a substituted ketenimine, and carbon monoxide with palladium(II) acetate and l,l -bis-diphenylphosphino-ferrocene (dppf) under thermal conditions gave the desired quinazolinone in near quantitative yield. In the same report, the authors showed that similar reactions could also be conducted with isocyanates and carbodiimides (not shown). 

Quinazolinone derivatives have been reported with various biological and medicinal properties, such as inhibitors of the epidermal growth factor (EGF) receptors of tyrosine kinase, and as anticancer, antiviral, and anti-tubercular agents. They are also used as ligands for benzodiazepine and... 

Hydroxy- and 4-ethoxy-3,4-dihydro-3-phenyl-2(lH)-quinazolinones as well as their thione analogs exhibit pseudobasic properties and may easily be condensed with 0-, N-, and C-nucleophiles (CH acids) by elimination of water or ethanol. Reactions with 0-, N-, and doubly activated C-nucleophiles (e. g. acetylacetone) may be effected by simply heating the components, while with the less reactive C-nucleophiles (monoketones) HCl must be used as catalyst. - E 4-Ethoxy-3,4-dihydro-3-phenylquinazolin-2(lH)-one dissolved in refluxing acetone, treated with a little coned. HCl, and refluxing continued 1 hr. 4-acetonyl-3,4-dihydro-3-phenylquinazolin-2(lH)-one. Y 71%. F.e. s. K. Lempert and P. Gyulai, Tetrahedron 26, 3443 (1970). 

The stmcturally related fused [2,l-b]quinazolinone alkaloids vasicinone 25, and its precursor deoxyvasicinone 26, are found in Biebersteinia multifida, Peganum harmala, and Adhatoda vasica that have anti-cancer, vasodilator (anti-hypertension), and bronchodilator (for treatment of asthma) properties. A solid-phase synthesis of vasicinone 25 and deoxyvasicinone 26 was reported by Reddy and colleagues in 2006 (Scheme 3.7). Resin-bound acid 21 was... 

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