30750-23-3

Usage

Structure

Quinazoline derivative with a nitrile functional group and a ketone group

Potential applications

Medicinal chemistry, particularly in the development of pharmaceutical drugs

Biological activity

Unknown, may exhibit biological activity

Synthesis

Could serve as a building block for the synthesis of various biologically active compounds

Further research

Needed to fully understand its properties and potential uses

InChI:InChI=1/C10H7N3O/c11-6-5-9-12-8-4-2-1-3-7(8)10(14)13-9/h1-4H,5H2,(H,12,13,14)

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 118-92-3 anthranilic acid 
• 90980-58-8 methyl 2-cyanoethanimidothioate 
• 76473-65-9 (4-oxo-4H-3,1-benzoxazin-2-yl)-2-acetonitrile 
• 77287-34-4 formamide 
• 60278-76-4 α-cyanoiminothioacetic acid ethyl ester 
• 622847-77-2 2-(4-oxo-3,4-dihydro-2-quinazolinyl)-2-(tetrahydro-2-furanylidene)acetonitrile 
• 1885-29-6 anthranilic acid nitrile 
• 219739-45-4 2-methoxyacetamidobenzonitrile 
• 21721-76-6 2-methoxymethylquinazolin-4(3H)-one 
• 34637-40-6 2-(hydroxymethyl)quinazolin-4(3H)-one 
• 19062-51-2 2-(bromomethyl)quinazolin-4(3H)-one 
• 107-91-5 cyanoacetic acid amide 
• 28144-70-9 anthranilic acid amide 

Downstream Products

• 133149-49-2 (E)-3-(4-Chloro-phenyl)-2-(4-oxo-3,4-dihydro-quinazolin-2-yl)-acrylonitrile 
• 133149-47-0 (E)-2-(4-Oxo-3,4-dihydro-quinazolin-2-yl)-3-phenyl-acrylonitrile 
• 133149-48-1 (E)-3-(4-Methoxy-phenyl)-2-(4-oxo-3,4-dihydro-quinazolin-2-yl)-acrylonitrile 
• 76473-43-3 (4-Ethoxy-quinazolin-2-yl)-acetonitrile 
• 872103-16-7 8-(2-hydroxybenzoyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carbonitrile 
• 21419-63-6 ethyl (4-oxo-3,4-dihydroquinazolin-2-yl)acetate 
• 1367601-15-7 3-(3-chlorophenyl)-3-oxo-2-(4-oxo-3,4-dihydroquinazolin-2(1H)ylidene)propanenitrile 
• 302803-65-2 3-oxo-2-(4-oxo-3,4-dihydroquinazolin-2(1H)ylidene)-3-phenylpropanenitrile 
• 302803-67-4 3-(4-chlorophenyl)-3-oxo-2-(4-oxo-3,4-dihydroquinazolin-2(1H)ylidene)propanenitrile 
• 307343-06-2 3-(2-chlorophenyl)-3-oxo-2-(4-oxo-3,4-dihydroquinazolin-2(1H)ylidene)propanenitrile 
• 76473-49-9 3-(α-benzylidene)cyanomethyl-4-quinazolyloxy(α'-benzylidene)acetic acid ethyl ester 
• 76473-48-8 2-(2-Cyanomethyl-quinazolin-4-yloxy)-N-p-tolyl-acetamide 

Relevant academic research and scientific papers

Solvent-free synthesis of quinazolin-4(3H)-ones promoted by SbCl3 under microwave condition

Efficient and fast condensation of anthranilic amide or anthranilic acid with various acylamides have been carried out using a catalytic amount of Antimony(UJ) chloride (SbCl3) under microwave irradiation to afford a series of 2-substituted quinazolin-4(3H)-ones in good to excellent yield (65-95%) without solvent The reactions have been carried out without solvent by one-pot reaction in several minutes and optimized. This method shows several advantages of a simple and rapid work-up procedure, a clean conversion, high yields and is environmentally friendly.

Chemical probes to study ADP-ribosylation: Synthesis and biochemical evaluation of inhibitors of the human ADP-ribosyltransferase ARTD3/PARP3

The racemic 3-(4-oxo-3,4-dihydroquinazolin-2-yl)-N-[1-(pyridin-2-yl)ethyl] propanamide, 1, has previously been identified as a potent but unselective inhibitor of diphtheria toxin-like ADP-ribosyltransferase 3 (ARTD3). Herein we describe synthesis and evaluation of 55 compounds in this class. It was found that the stereochemistry is of great importance for both selectivity and potency and that substituents on the phenyl ring resulted in poor solubility. Certain variations at the meso position were tolerated and caused a large shift in the binding pose. Changes to the ethylene linker that connects the quinazolinone to the amide were also investigated but proved detrimental to binding. By combination of synthetic organic chemistry and structure-based design, two selective inhibitors of ARTD3 were discovered.

QUINAZOLINONE INHIBITORS OF DYNEIN

Compounds of formula (I) in which R3 is chosen from hydrogen, cyano, nitro, acetyl and C(=O)NH2, and Ar is optionally substituted monocyclic or bicyclic aryl or heteroaryl, are useful as antitumor agents

Reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with aldehydes

The reaction of 2-hetaryl-2-(tetrahydro-2-furanylidene)acetonitriles with a electrophilic reagent (anisaldehyde) was studied. It was shown that condensation of the latter with 2-(4-oxo-3,4-dihydro-2-quinazolyl)- and 2-(1H-benzo[d]imidazol-2-yl)-2-(tetrahydro-2-furanylidene)acetonitriles in the presence of secondary amines or acids takes place with elimination of the furan fragment and the formation of 3-aryl-2-(4-oxo-3,4-dihydro-2-quinazolinyl)- and 2-(1H-benzo[d]imidazol-2-yl)acrylo-nitriles.

Solvent-free syntheses of some quinazolin-4(3H)-ones derivatives

Solvent-free syntheses of quinazolin-4(3H)-ones were performed by reaction of anthranillic acid with different amides, such as nicotinamide, benzamide, formamide, etc., on montmorillonite K-10. Products were confirmed by FTIR, 1HNMR, and 13CNMR spectroscopic techniques. All synthesized compounds exhibited antioxidant properties and have been compared with standard antioxidant BHT.

Synthesis and properties of 6,7,8-substituted 2-(4-oxo-3,4-dihydro-2-quinazolinyl)-acetonitriles

2-N-Oxo-3,4-dihydro-2-quinazolinyl)acetonitriles have been obtained by the interaction of α-cyanoethylthioiminoacetate with substituted anthranilic acids. Prototropy became apparent in the series of synthesized compounds. Reactions of the 2-(4-oxo-3,4-dihydro-2-quinazolinyl)acetonitriles have been carried out with (hereto)aromatic aldehydes leading to the formation of 3-aryl-2-(4-oxo-3,4-dihydro-2-quinazolinyl)acrylonitriles.

α-Cyanothioacetamide and its Derivatives in Heterocyclic Synthesis: Preparation of Several New 4-Oxoquinazoline Derivatives

The reaction of α-cyanothioacetamide (1) or its methylthio derivative (2) with anthranilic acid led to the formation of 3,4-dihydro-4-oxoquinazolin-2-yl acetonitrile (3). 3 condensed with aromatic aldehydes to give arylidene derivatives (4a-d) which could be prepared also via the reaction of 2-thiocarbamoylcinnamonitriles (5a-d) or their methylthio derivatives (6a-d) with anthranilic acid. 3 reacted with cinnamonitrile derivatives (7a-h) and (12a-d) to yield pyrido--quinazoline derivatives (10a-h) and (15a-d) which could also be prepared by the reaction of (4a-d) with malononitrile (11a), benzoyl acetonitrile (11b) and ethylcyanoacetate (16), respectively.

Reactions of 2-Cyanomethyl-3,1-benzoxazin-4(H)-one: Synthesis of Quinazoline and 4H-3,1-Benzothiazine Derivatives and Other Heterocycles

Reactions of 2-cyanomethyl-3,1-benzoxazin-4(H)-one (1a) with aryldiazonium chlorides, benzaldehyde, formamide, phosphorus pentasulphide and sodium azide have been investigated.The quinazolinone (4), obtained by the action of formamide on 1a, reacts with dialkyl sulphate, phosphorus oxychloride, methylmagnesium iodide and ethyl chloroacetate to give 4-alkoxy-2-cyanomethylquinazolines (5a,b), 4-chloro-2-cyanomethylquinazoline (5d), 2-acetonylquinazolin-4(3H)-one (6) and 2-cyanomethyl-4-quinazolyloxyacetic acid ethyl ester (5c), respectively.The ester (5c) on condensation with hydrazine hydrate and amines gives the corresponding amides (5e-g) whereas with benzaldehyde in the presence of NaOEt, it gives 3-(α-benzylidene)cyanomethyl-4-quinazolyloxy(α'-benzylidene)acetic acid ethyl ester (7).However, 5c undergoes Stobbe condensation in the presence of potassium t-butoxide to give 8. 2-Cyanomethyl-3,1-benzothiazine-4(H)-thione (9), obtained by the action of P2S5 on 1a, reacts with Grignard reagents and amines or hydrazine hydrate to give carbinols (10a-d) and thioamides (10e-j) respectively.The thione (9) on heating with copper bronze in xylene gives 4,4'-bi-3,1-benzothiazine>-2,2'-diacetonitrile (11)