20197-85-7

Upstream product

• 27631-29-4 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 
• 124-41-4 sodium methylate 

Downstream Products

• 253192-01-7 4-[1-(4-hydroxy-6,7-dimethoxy-quinazolin-2-yl)-piperidin-4-ylamino]-benzoic acid tert-butyl ester 
• 253192-00-6 4-[1-(4,6,7-Trimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis and Structure-Photophysics Evaluation of 2-N-Amino-quinazolines: Small Molecule Fluorophores for Solution and Solid State

2-N-aminoquinazolines were prepared by consecutive SNAr functionalization. X-ray structures display the nitrogen lone pair of the 2-N-morpholino group in conjugation with the electron deficient quinazoline core and thus representing electronic push-pull systems. 2-N-aminoquinazolines show a positive solvatochromism and are fluorescent in solution and in solid state with quantum yields up to 0.73. Increase in electron donor strength of the 2-amino substituent causes a red-shift of the intramolecular charge transfer (ICT) band (300–400 nm); whereas the photoluminescence emission maxima (350–450 nm) is also red-shifted significantly along with an enhancement in photoluminescence efficiency. HOMO-LUMO energies were estimated by a combination of electrochemical and photophysical methods and correlate well to those obtained by computational methods. ICT properties are theoretically attributed to an excitation to Rydberg-MO in SAC-CI method, which can be interpreted as n-π* excitation. 7-Amino-2-N-morpholino-4-methoxyquinazoline responds to acidic conditions with significant increases in photoluminescence intensity revealing a new turn-on/off fluorescence probe.

Antibacterial quinazoline compounds

Provided are compounds of formula (I) wherein X, Y and Z are independently CH or N; n is 0 or 1; R1 is selected from OH, alkoxy, aryloxy, aralkyloxy and guanidinyl; R2 and R3 are independently selected from H, halogen, amino, hydroxyl, nitro, cyano and carboxyl; R4 is H, alkyl or acyl; R5 is selected from H, hydroxyl, halogen, nitro, alkyl, alkoxy, amino, cyclic amino, alkylamino, arylamino and aralkylamino wherein the alkyl, aryl and cyclic moieties are optionally substituted; R6 and R7 are independently selected from H, alkyl, alkoxy, halogen and amino; and R8 and R9 are independently selected from H, C1-4 alkyl, alkoxy, acyl, acyloxy, alkoxycarbonyl, hydroxyl, halogen, amino and carboxyl. The compounds have therapeutic or prophylactic use for treating bacterial infection in mammals.