SYNTHESIS OF N-(4-(((6-NITROQUINAZOLIN-4- YL)AMINO)METHYL)PHENYL)MORPHOLINE-4-CARBOXAMIDE
Keywords:
quinazoline, organic synthesis, cyclizationAbstract
Quinazolines, as fused bicyclic heterocycles, are of particular importance in organic synthesis and medicinal chemistry. In the present study, the targeted synthesis of a novel compound, N- (4-(((6-nitroquinazolin-4-yl)amino)methyl)phenyl)morpholine-4-carboxamide, was achieved in high yield. This molecule represents a key intermediate for the preparation of 4,6-disubstituted quinazoline derivatives. The structure of the obtained compound was confirmed by modern physicochemical methods, including 1H NMR, 13C NMR, and HRMSReferences
1. Marshall, C.M., et al., An Update on the Nitrogen Heterocycle Compositions and Properties of
U.S. FDA-Approved Pharmaceuticals (2013-2023). J Med Chem, 2024. 67(14): p. 11622-11655.
2. Vitaku, E., D.T. Smith, and J.T. Njardarson, Analysis of the structural diversity, substitution
patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J Med
Chem, 2014. 57(24): p. 10257-74.
3. Bala, I.A., A.M. Asiri, and R.M. El-Shishtawy, Quinazoline derivatives and hybrids: recent
structures with potent bioactivity. Medicinal Chemistry Research, 2024. 33(12): p. 2372-2419.
4. Das, D. and J. Hong, Recent advancements of 4-aminoquinazoline derivatives as kinase
inhibitors and their applications in medicinal chemistry. Eur J Med Chem, 2019. 170: p. 55-72.
5. Herrera-Vázquez, F.S., F. Hernández-Luis, and J.L. Medina Franco, Quinazolines as inhibitors
of chromatin-associated proteins in histones. Medicinal Chemistry Research, 2019. 28(4): p. 395-416.
6. Haghighijoo, Z., et al., Therapeutic potential of quinazoline derivatives for Alzheimer's disease:
A comprehensive review. Eur J Med Chem, 2022. 227: p. 113949.
7. Shagufta and I. Ahmad, An insight into the therapeutic potential of quinazoline derivatives as
anticancer agents. Medchemcomm, 2017. 8(5): p. 871-885.
8. Ayala-Aguilera, C.C., et al., Small Molecule Kinase Inhibitor Drugs (1995-2021): Medical
Indication, Pharmacology, and Synthesis. J Med Chem, 2022. 65(2): p. 1047-1131