28831-35-8

Basic information

• Product Name: Acetic acid, [(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]-, ethyl ester
• CAS NO: 28831-35-8
• Molecular Formula: C18H16N2O3S
• Molecular Weight: 340.403
• Mol File: 28831-35-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Acetic acid, [(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]-, ethyl ester(28831-35-8)
• EPA Substance Registry System: Acetic acid, [(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]-, ethyl ester(28831-35-8)

Safety Data

• Hazardous Substances Data: 28831-35-8(Hazardous Substances Data)

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 18741-24-7 2-mercapto-3-phenyl-3H-quinazolin-4-one 
• 18741-24-7 3-phenyl-2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 105-36-2 ethyl bromoacetate 
• 118-92-3 anthranilic acid 
• 103-72-0 phenyl isothiocyanate 
• 28144-70-9 anthranilic acid amide 

Downstream Products

• 87439-71-2 N-Butyl-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 87439-70-1 N-Methyl-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 87439-72-3 N-Benzyl-2-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-ylsulfanyl)-acetamide 
• 727-63-9 3,4-dihydro-2-fluoro-4-oxo-3-phenylquinazoline 
• 250690-57-4 ethyl α-fluoro-α-[(3,4-dihydro-4-oxo-3-phenyl-2-quinazolinyl)thio]acetate 
• 1028-37-1 1-methyl-3-phenylquinazoline-2,4(1H,3H)-dione 
• 128650-95-3 ethyl-2-(3-phenyl-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetate 
• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 1377459-47-6 N-(1,3-dioxoisoindolin-2-yl)-2-[(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio]acetamide 

Relevant articles and documents

2-thioquinazolinone compound and preparation method and application thereof

The invention provides a 2-thioquinazolinone compound and a preparation method and application thereof, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: mixing an anthranilamide compound, an isothiocyanate compound, a bromide and a polar organic solvent, and carrying out a series cyclization reaction in an air atmosphere to obtain the 2-thioquinazolinone compound. According to the preparation method, the 2-thioquinazolinone compound can be prepared by one-step reaction without adding a catalyst, the yield and the purity of the product are high, the reaction route is simple, the operation is simple, and the preparation method is suitable for industrial production.

Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N -(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a-o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells.

Synthesis of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate

A series of methyl [3-alkyl-2-(2,4-dioxo-3,4-dihydro-2H-quinazolin-1-yl)-acetamido] alkanoate 10-13a-f has been developed on the basis of the N-chemoselective reaction of 3-substituted quinazoline-2,4-diones 3a-d with ethyl chloroacetate and azide coupling method with amino acid ester hydrochloride. The precursor quinazoline diones 3a-d chemoselective reactions were studied using DFT(B3LYP)/6-311G level of theory and were prepared by a new rearrangement method from the corresponding 2-(3-methyl-4-oxo-3,4- dihydroquinazolin-2-ylthio) acetohydrazide 6. {figure presented}.