70589-51-4

Upstream product

• 38163-38-1 methyl 2-(isobutyrylamino)benzoate 
• 118-92-3 anthranilic acid 
• 79-30-1 isobutyryl chloride 
• 134-20-3 2-carbomethoxyaniline 
• 173371-71-6 3-(2,2-Dimethylpropanoyl)amino-2-isopropyl-3,4-dihydroquinazolin-4-one 
• 144522-58-7 3-acetylamino-2-isopropylquinazolin-4(3H)-one 

Downstream Products

• 178422-75-8 N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-2-phenylpropionamide 
• 144522-58-7 3-acetylamino-2-isopropylquinazolin-4(3H)-one 
• 425380-28-5 3-[N-(3-m-acetoxyphenylpropanoyl)-N-(3-phenylpropanoyl)amine]-2-isopropylquinazolin-4(3H)-one 
• 13182-64-4 2-Isopropyl-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and in silico study of novel library sulfonates containing quinazolin-4(3H)-one derivatives as potential aldose reductase inhibitors

A series of novel sulfonates containing quinazolin-4(3H)-one ring derivatives was designed to inhibit aldose reductase (ALR2, EC 1.1.1.21). Novel quinazolinone derivatives (1–21) were synthesized from the reaction of sulfonated aldehydes with 3-amino-2-alkylquinazolin-4(3H)-ones in glacial acetic acid with good yields (85%–94%). The structures of the novel molecules were characterized using IR, 1H-NMR, 13C-NMR, and HRMS. All the novel quinazolinones (1–21) demonstrated nanomolar levels of inhibitory activity against ALR2 (KIs are in the range of 101.50–2066.00 nM). Besides, 4-[(2-isopropyl-4-oxoquinazolin-3[4H]-ylimino)methyl]phenyl benzenesulfonate (15) showed higher inhibitor activity inhibited ALR2 up to 7.7-fold compared to epalrestat, a standard inhibitor. Binding interactions between ALR2 and quinazolinones have been investigated using Schr?dinger Small-Molecule Drug Discovery Suite 2021–1, reported possible inhibitor-ALR2 interactions. Both in vitro and in silico study results suggest that these quinazolin-4(3H)-one ring derivatives (1–21) require further molecular modification to improve their drug nominee potency as an ALR2 inhibitor.

QUINAZOLINONES AND THEIR USE AS POTASSIUM CHANNELS ACTIVATORS

This invention relates to novel quinazolinone derivatives of formula (I) having medical utility, to use of the quinazolinone derivatives of the invention for the manufacture of a medicament, to pharmaceutical compositions comprising the quinazolinone deri

Quinazolin-4-one derivatives

A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R5)— or the formula —NH—CH(R5)—, R1, R2, R3, and R4 represent a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or a hydroxy group, R5 represents a C1 to C6 alkyl group or a C6 to C10 aryl group, and R represents an amino group.

Lithiation of 3-(acylamino)-2-unsubstituted-, 3-(acylamino)-2-ethyl-, and 3-(acylamino)-2-propyl-4(3H)-quinazolinones: Convenient syntheses of more complex quinazolinones

3-(Pivaloylamino)- and 3-(acetylamino)-4(3H)-quinazolinones react with alkyllithium reagents to give 1,2-addition products in very good yields. Lithiation takes place with LDA and is regioselective at position 2. The lithium reagents thus obtained react with a variety of electrophiles to give the corresponding substituted derivatives in very good yields. Reactions of the lithium reagents with iodine give oxidatively dimerized cyclic structures. 3-(Pivaloylamino)- and 3-(acetylamino)-2-ethyl-4(3H)-quinazolinones and 3-(pivaloylamino)- and 3-(acetylamino)-2-propyl-4(3H)-quinazolinones are lithiated at the benzylic position with LDA. The lithium reagents so produced also react with a variety of electrophiles to give the corresponding 2-substituted-4(3H)-quinazolinone derivatives in very good yields. However, lithiation of 3-(acylamino)-2-(1-methylethyl)-4(3H)-quinazolinones was unsuccessful, as were lithiations of compounds having a diacetylamino group at position 3. The amide groups have been cleaved in good yield under basic or acidic conditions from some of the products to provide access to the free amino compounds.

Reaction of 3-(Acetoxyamino)quinazolin-4(3H)-ones with Enolic β-Diketones: the N-N Bond as a Chiral Axis in N-(3,4-dihydro-4-oxoquinazolin-3-yl)-N-acyl-α-aminoketones; Reductive and Base-catalysed Cleavage of the N-N Bond in N-Acetyl-N-(3,4-dihydro-4-oxoquinazolin-3-yl)-α-amino Aci...

Following the method of Foucaud and coworkers, reaction of pentane-2,4-dione with 3-(acetoxyamino)quinazolin-4-one 8 gave the keto amide 9 (15percent). 3-Methylpentane-2,4-dione reacts with compound 8 to give a relatively stable enol 11 (66percent) which can be isolated in a crystalline form.Rotation around the N-N bonds in both compounds 9 and 11 is believed to be slow on the real time-scale and hence the N-N bonds can be considered as a chiral axes.As a result, protonation of the enol double bond in compound 11 and the creation of an additional chiral centre, gives rise to the separable keto amides 14 and 15; this protonation can be accomplished completely diastereoselectively.Lead tetraacetate acetoxylation of compound 11 to give compound 11 to give compound 19 is also completely diastereoselective.Brief heating of the enol effects the elimination of the quinazolinone and the formation of the N-acetylimine 16 via an 8-membered transition state.Base-catalysed elimination of the quinazolinone ring from compound 22 is surprisingly easy: reductive cleavage of this N-N bond in compound 22 is facile by comparison with the 3-(alkylamino)quinazolin-4-ones.