Synthesis, structures elucidation, DNA-PK, PI3K and antiplatelet activity of a series of novel 7- or 8-(N-substituted)-2-morpholino-quinazolines

Heppell, Jacob T.; Al‐Rawi, Jasim M. A.

doi:10.1007/s00044-016-1608-9

Cited by 2 publications

(1 citation statement)

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“…4‐Methoxy‐2‐ N ‐morpholino‐7‐aminoquinazoline (12) : [58] A 1 M aq. HCl solution (0.6 mL) was added to a mixture of compound 11 (58.0 mg, 0.20 mmol) and iron powder (35 mg, 0.60 mmol) in EtOH (10 mL) and kept reflux for 3 h. The mixture was cooled down and filtered.…”

Section: Methodsmentioning

confidence: 99%

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

Motoyama

Doan

Hibner-Kulicka

et al. 2021

Chemistry An Asian Journal

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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.

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Section: Methodsmentioning

confidence: 99%