5632-37-1

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-OXOPROPYL)-4(3H)-QUINAZOLINONE is used as a potential antitumor agent for its ability to target and inhibit the growth of cancer cells. Its antitumor properties make it a candidate for the development of new cancer therapies.
3-(2-OXOPROPYL)-4(3H)-QUINAZOLINONE is also used as an antimicrobial agent due to its ability to combat various types of bacteria and other microorganisms, which can be beneficial in the treatment of infections and the development of new antibiotics.
Used in Anti-inflammatory Applications:
3-(2-OXOPROPYL)-4(3H)-QUINAZOLINONE is used as an anti-inflammatory agent for its potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Analgesic Applications:
3-(2-OXOPROPYL)-4(3H)-QUINAZOLINONE is used as an analgesic agent for its potential to relieve pain, making it a candidate for the development of new pain management therapies.

InChI:InChI=1/C11H10N2O2/c1-8(14)6-13-7-12-10-5-3-2-4-9(10)11(13)15/h2-5,7H,6H2,1H3

Upstream product

• 491-36-1 4-Hydroxyquinazoline 
• 78-95-5 chloroacetone 
• 598-31-2 1-bromoacetone 
• 491-36-1 4-quinazolinol 
• 28144-70-9 anthranilic acid amide 
• 118-92-3 anthranilic acid 

Downstream Products

• 330798-23-7 (3S)-trans-O-acetyl-N-benzyloxycarbonyl-febrifugine 
• 24159-07-7 febrifugine 
• 249744-04-5 3-(2-oxo-3-triphenylphosphoranediylpropyl)-4(3H)-quinazolinone 
• 249744-06-7 3-[2-oxo-3-(1-benzyloxycarbonyl-2-piperidyl)propyl]-4(3H)-quinazolinone 
• 249744-05-6 3-(8-benzyloxycarboxamido-2-oxo-3-octenyl)-4(3H)-quinazolinone 
• 24159-07-7 dl-febrifugine 

Relevant academic research and scientific papers

Synthesis and antiproliferative evaluation of oxime, methyloxime, and amide-containing quinazolinones

Certain oxime, methyloxime, and amide-containing quinazolinone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against a panel of human cancer cell lines including nasopharyngeal carcinoma (NPC-TW01), lung carcinoma (NCI-H226), and leukemia (Jurkat). Quinazolinone 2 was inactive against all three cell lines tested, while quinazolinone 4 was weakly active against both Jurkat and H226 cancer cells with IC50 values of 6.55 and 12.27 μM, respectively, indicating that the oxime derivative 4 is more favorable than its ketone precursor 2. Our results have also indicated that quinazolinone 8g and its biphenyl counterpart 8f exhibited more potent antiproliferative activities than the positive control methotrexate against all three cancer cell lines tested. Among these quinazolinone derivatives, 8g was the most active against NPC-TW01 with an IC50 value of 4.78 μM. Further study on NPC-TW01 cell cycle distribution indicated that the compound 8g induced cell arrest at the G1/G0 phase in a time- and concentration-dependent manner. Moreover, a characteristic hypo-diploid DNA content peak (sub-G1) was found to increase from 1 to 4% in NPC-TW01 cells treated with 8g for 72 hr. These results indicate that 8g can induce cells arrest in the G1/G0 phase and cause cell death. Further structural optimization of 8g and detailed study of its antiproliferative mechanism are going on.

Synthesis of new N3-substituted quinazolin-4(3H)one derivatives

Quinazolin-4-one (1) was synthesized by reacting anthranilic acid with excess of formamide, which was N-alkylated with chloroacetone to form quinazolin-4-one-3-yl propan-2-one (2). The interaction of 2 with phenylhydrazine, 2,4-dinitrophenylhydrazine and semicarbazide gave the corresponding hydrazones (3). Further, the treatment of 2 with hydrazine hydrate yielded hydrazino derivative (4) which was condensed with variously substituted aryl aldehydes to form the corresponding hydrazones (5). The compound 4 on cyclization with ammonium acetate gave tricyclic compound (6). Further, compound 2 on reaction with hydroxylamine hydrochloride yielded oxime (7), and the corresponding oxime carbamates (8) with phenyl isothiocyanate and phenyl isocyanate.

Synthesis and antimalarial activity of dldeoxyfebrifugine

dl-Deoxyfebrifugine (3) was synthesized from 2-piperidone (4) by two methods via the Wittig reaction of 2-hydroxypiperidine (6). The antimalarial activity of 3 was discussed.

The preparation of α-substituted, β-hydroxy piperidines and pyrrolidines: The total synthesis of febrifugine

Epoxides generated from cyclic ene carbamates are effective N-acyl iminium ion precursors and allow for the preparation of β-hydroxy, α-substituted piperidines and pyrrolidines. The total synthesis of racemic Febrifugine is also described.

THE CHEMICAL SIMULATION OF THE "ATP-IMIDAZOLE" CYCLE

The synthetic strategy inherent in the "ATP-Imidazole" cycle and centred around the vicinal disposition of -NH2 and -CONH2 functions, has been demonstrated with anthranilamide (2) and 1-benzyl-5-aminoimidazole-4-carboxamide (1) as regeneratable carriers involving specifically N-alkylated quinazolin-4-ones, hypoxantines and adenines, as key intermediates.The isolation and characterization of the enamine (22) coupled with other observations has made it possible to rationalize the pathways involved in these cyclic operations.The practical utility of the synthetic strategy using regeneratable carriers has beem illustrated with the synthesis of a range of 1,5-disubstituted imidazoles.Whilst pathways leading to specific N-alkylation in the Natural cycle and in simulation studies are comparable, the subsequent events take place in a reverse order, primarily because of the divergence in the hydrolitic profile of the alkylated substrates.The action of dilute alkali on 3-alkylated quinazolin-4-ones leads to 2-3 rather than 3-4 bond rupture.Endeavours to promote the latter path, by blocking the 2 position gave unexpected results. 2-Methyl-3-phenacyl quinazolin-4-one gave with dilute alkali the novel aromatic tricyclic system (32) from trans-annular cyclization.On the other hand the 2-blocked 3-benzamido quinazolin-4-ones (33) and (34) gave triazoles (35) and (36) arising from the desired 3-4 rupture followed by cyclization initiated by the resulting amidine unit. 2-Phenil-3-benzamidoquinazolin-4-one (34) with distilled water at 200 deg C gave a number of products whicc have been identified and their formation explained.

SYNTHESIS ON TEMPLATES: REGIOSPECIFIC SYNTHESIS OF IMIDAZOLES

A new, biomimetic template operated strategy has been developed leading to regiospecific synthesis of imidazoles.