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Usage

Uses

Used in Pharmaceutical Industry:
8-Chloro-2-methylquinazolin-4(3H)-one is used as a pharmaceutical intermediate for the development of new drugs. Its anticonvulsant and antitumor properties make it a promising candidate for the treatment of various neurological disorders and cancer types, respectively.
Used in Medicinal Chemistry Research:
8-Chloro-2-methylquinazolin-4(3H)-one serves as a subject of interest in medicinal chemistry research. Its unique structure and properties allow researchers to investigate its potential as a lead compound for the development of novel therapeutic agents with improved efficacy and selectivity.
Used in Drug Discovery and Development:
8-Chloro-2-methylquinazolin-4(3H)-one is utilized in drug discovery and development processes. Its pharmacological activities and potential applications in treating neurological disorders and cancer make it a valuable compound for further exploration and optimization to enhance its therapeutic potential.

InChI:InChI=1/C9H7ClN2O/c1-5-11-8-6(9(13)12-5)3-2-4-7(8)10/h2-4H,1H3,(H,11,12,13)

Upstream product

• 6388-47-2 2-amino-3-chlorobenzoic acid 
• 75-05-8 acetonitrile 
• 108-24-7 acetic anhydride 

Relevant academic research and scientific papers

A copper-catalyzed Ritter-type cascade via iminoketene for the synthesis of quinazolin-4(3H)-ones and diazocines

We have developed a copper-catalyzed Ritter-type reaction/cyclization cascade of anthranilic acids and nitriles, affording the quinazolin-4(3H)-ones. The cascade proceeds through a Ritter-type reaction capturing the iminoketene intermediates by nitriles. Furthermore, we found a novel Ritter-type reaction/condensation/intramolecular anti-Markovnikov hydroamination cascade, providing access to functionalized diazocines in one-pot.

Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

We have demonstrated that quinazolin-4(3H)-one, a nicotinamide (NI) mimic with PARP-1 inhibitory activity in the high micromolar range (IC50 = 5.75 μM) could be transformed into highly active derivatives with only marginal increase in molecular weight. Convenient one to two synthetic steps allowed us to explore extensive SAR at the 2-, and 5- through 8-positions of the quinazolin-4(3H)-one scaffold. Substitutions at the 2- and 8-positions were found to be most favorable for improved PARP-1 inhibition. The amino group at 8-position resulted in compound 22 with an IC50 value of 0.76 μM. Combination of the 8-amino substituent with an additional methyl substituent at the 2-position provided the most potent compound 31 [8-amino-2-methylquinazolin- 4(3H)-one, IC50 = 0.4 μM] in the present study. Compound 31 inhibited the proliferation of Brca1-deficient cells with an IC50 value of 49.0 μM and displayed >10-fold selectivity over wild type counterparts. Binding models of these derivatives within the active site of PARP-1 have further supported the SAR data and will be useful for future lead optimization efforts.