214287-99-7

Usage

Uses

Used in Pharmaceutical Industry:
(4S)-6-CHLORO-4-((E)-2-CYCLOPROPYLVINYL)-4-(TRIFLUOROMETHYL)-3,4-DIHYDROQUINAZOLIN-2(1H)-ONE is used as a pharmaceutical compound for its potential therapeutic applications. The compound's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Antiviral Applications:
In the field of antivirals, (4S)-6-CHLORO-4-((E)-2-CYCLOPROPYLVINYL)-4-(TRIFLUOROMETHYL)-3,4-DIHYDROQUINAZOLIN-2(1H)-ONE is used as an antiviral agent, particularly as a non-nucleoside reverse-transcriptase inhibitor. It helps control the replication of genetic material in viruses, such as HIV, by inhibiting the reverse transcriptase enzyme, which is crucial for the virus's replication process.
Used in Chemical Research:
(4S)-6-CHLORO-4-((E)-2-CYCLOPROPYLVINYL)-4-(TRIFLUOROMETHYL)-3,4-DIHYDROQUINAZOLIN-2(1H)-ONE is also utilized in chemical research as a starting material or intermediate for the synthesis of other complex organic molecules. Its unique structural features make it a valuable building block for the development of novel chemical entities with potential applications in various fields.
Used in Material Science:
The specific properties of (4S)-6-CHLORO-4-((E)-2-CYCLOPROPYLVINYL)-4-(TRIFLUOROMETHYL)-3,4-DIHYDROQUINAZOLIN-2(1H)-ONE may also find applications in material science, where it could be used to develop new materials with specific characteristics, such as improved stability or reactivity.

InChI:InChI=1/C14H12ClF3N2O/c15-9-3-4-11-10(7-9)13(14(16,17)18,20-12(21)19-11)6-5-8-1-2-8/h3-8H,1-2H2,(H2,19,20,21)/b6-5+/t13-/m0/s1

Upstream product

• 497235-37-7 6-chloro-1-[(4-methoxyphenyl)methyl]-4-(trifluoromethyl)hydroquinazolin-2-one 
• 1414889-37-4 (S,Z)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one 
• 909547-84-8 (S)-1-(4-methoxybenzyl)-6-chloro-4-(2-cyclopropyl-2-oxoethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one 
• 1360591-23-6 (S,E)-6-chloro-4-(2-cyclopropylvinyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one 
• 1414889-36-3 C₁₈H₁₄ClF₃N₂O₃ 
• 1414889-08-9 (R)-6-chloro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazoline-4-carbonitrile 
• 1126895-93-9 (4S)-6-chloro-4-(2-cyclopropyl-2-hydroxyethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one 
• 214287-88-4 (4S)-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1,3,4-trihydroquinazolin-2-one 

Relevant academic research and scientific papers

Hydrogen-bond-directed enantioselective decarboxylative mannich reaction of β-ketoacids with ketimines: Application to the synthesis of anti-HIV drug DPC 083

Key to success: The title reaction provides facile access to enantioenriched 3,4-dihydroquinazolin-2(1H)-ones containing a quaternary stereogenic center in high yields with excellent enantioselectivities. Subsequent transformations lead to the convenient preparation of the anti-HIV drug DPC 083 and N-fused polycyclic compounds without loss of enantiomeric excess.

Highly enantioselective decarboxylative Mannich reaction of malonic acid half oxyesters with cyclic trifluoromethyl ketimines: Synthesis of β-amino esters and anti-HIV drug DPC 083

An organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half oxyesters with cyclic ketimines was developed for the preparation of enantioenriched β-amino esters with a quaternary stereogenic center and the anti-HIV drug DPC 083 (see scheme). Copyright

Highly enantioselective organocatalytic Strecker reaction of cyclic N-acyl trifluoromethylketimines: Synthesis of anti-HIV drug DPC 083

A highly efficient, organocatalytic, enantioselective Strecker reaction of cyclic N-acyl ketimines was developed for the preparation of enantioenriched cyclic α-amino nitriles with a quaternary carbon stereocentre and anti-HIV drug DPC 083. This journal is

Highly enantioselective organocatalytic Strecker reaction of cyclic N-acyl trifluoromethylketimines: Synthesis of anti-HIV drug DPC 083

A highly efficient, organocatalytic, enantioselective Strecker reaction of cyclic N-acyl ketimines was developed for the preparation of enantioenriched cyclic α-amino nitriles with a quaternary carbon stereocentre and anti-HIV drug DPC 083. The Royal Society of Chemistry 2012.

Highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by asymmetric Mannich reaction and chiral recognition

The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described. The key transformation was to establish the chiral trifluoromethyl quaternary carbon center bya diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline. An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed. A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>99.9 ee) simplyby reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA).

Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors

A series of 4-alkenyl and 4-alkynyl-3,4-dihydro-4-(trifluoromethyl)-2- (1H)-quinazolinones were found to be potent non-nucleoside reverse transcriptase inhibitors (NNRTIs) of human immunodeficiency virus type-1 (HIV-1). The 4-alkenyl-3,4-dihydro-4-(triflu

4,4-disubstituted-3,4-dihydro-2(1H)-quinazolinones useful as HIV reverse transcriptase inhibitors

The present invention relates to 4,4-disubstituted-3,4-dihydro-2(1H)-quinazolinones of formula I: or steroisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent, wherein: R1 is C1-3 alkyl substituted with 1-7 halogen; R2 is optionally substituted C1-5 alkyl, optionally substituted C2-5 alkenyl, or optionally substituted C2-5 alkynyl; R3, at each occurrence, is independently selected from C1-4 alkyl, OH, C1-4 alkoxy, F, Cl, Br, I, NR5R5a, NO2, CN, C(O)R6, NHC(O)R7, and NHC(O)NR5R5a; R5 and R5a are independently selected from H and C1-3 alkyl; R6 is selected from H, OH, C1-4 alkyl, C1-4 alkoxy, and NR5R5a; R7 is selected from C1-3 alkyl and C1-3 alkoxy; R8 is selected from H, C3-5 cycloalkyl, and C1-3 alkyl; and, n is selected from 0, 1, 2, 3, and 4.

Expanded-spectrum nonnucleoside reverse transcriptase inhibitors inhibit clinically relevant mutant variants of human immunodeficiency virus type 1

A research program targeted toward the identification of expanded- spectrum nonnucleoside reverse transcriptase inhibitors which possess increased potency toward K103N-containing mutant human immunodeficiency virus (HIV) and which maintain pharmacokinetic