UV identification substitution position of pyrimidine ring
DOI:
https://doi.org/10.12775/MBS.2015.032Keywords
UV and 1H NMR spectroscopy, N1 and N3-alkyl substituted uracil, bathochromic shift, hypsochromic shiftAbstract
Pyrimidine is six-member heterocyclic compound that contains two nitrogen atoms at positions 1 and 3. Pyrimidine derivatives have showed various biological activities such as antimicrobial, antitumor, antifungal, the hypnotic and sedative activities. The oxopyrimidnes of the biological activity of the most possess substituents at the N1 or N3 position [1-11].
This paper presents identification the location of the N1 and N3 isomeric substituents of the pyrimidine derivatives. The UV spectroscopy was used for this purpose. This method is simple, economical and does not require large quantities of sample.
The absorption maxima of the 1 and 3-substituted pyrimidine derivatives were sensitive to the addition of base. In alkaline solution the N3-alkyl substituted uracil showed bathochromic shift, but the absorption maxima of N1 analogs shift toward shorter wavelengths (the hypsochromic shift) (Figure 1, 2, 3). This was associated with the formation of monoanion, which was created as a result of dissociation of a proton from the nitrogen atom (Scheme 2).
The results were compared with the results that may be obtained from the analysis of proton nuclear magnetic resonance 1H NMR (Scheme 1, 3, 4). The NMR spectroscopy is a method much more precise and it can provide more information about the structure of the compound. By 1H NMR is not always possible clearly distinguish between N1 and N3 isomers, in contrast to the UV spectroscopy.
References
(1) Gopalsamy A., Bennett E. M., Shi M., Identification of pyrimidine derivatives as hSMG-1 inhibitor, Bioorganic & Medicinal Chemistry Letters, 2012, 22, 6636–6641.
(2) Zhu W., Liu Y., Zhai X., Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents, Eur. J. Med. Chem., 2012, 162-175.
(3) Lukasik P. M., Elabar S., Lam F., Synthesis and biological evaluation of imidazo[4,5-b]pyridine and
-heteroarylpyrimidine derivatives as anti-cancer agents, Eur. J. Med. Chem., 2012, 57, 311-322.
(4) Kassab A. E., Gedawy E. M., Synthesis and anticancer activity of novel 2-pyridyl hexahyrocyclooctathieno[2,3-d]pyrimidine derivatives, Eur. J. Med. Chem., 2013, 63, 224-230.
(5) Coen N., Singh U., Vuyyuru V., Activity and mechanism of action of HDVD, a novel pyrimidine nucleoside derivative with high levels of selectivity and potency against gammaherpesviruses, Journal of Virology, 2013, 87, 3839–3851.
(6) Abd El Hamid M. K., Mihovilovic M. D., El-Nassan H. B., Synthesis of novel pyrazolo[3,4-d]pyrimidine derivatives as potential anti-breast cancer agents, Eur. J. Med. Chem., 2012, 57, 323-328.
(7) Zenker N., Thyroid function and thyroid drugs. In: Principles of Medicinal Chemistry. Foye W.O., Lea & Febiger: Philadelphia, London, UK, 1990, 603-621.
(8) Del Carmen Núñeza M., Entrena A., Rodríguez-Serrano F., Synthesis of novel 1-(2,3-dihydro-5H-4,1-benzoxathiepin-3-yl)-uracil and -thymine, and their corresponding S-oxidized derivatives, Tetrahedron, 2005, 61, 10363-10369.
(9) Prachayasittikul S., Sornsongkhram N., Pingaew R., Synthesis of N-Substituted 5-iodouracils as antimicrobial and anticancer agents, Molecules, 2009, 14, 2768-2779.
(10) Semenov V. E., Voloshina A. D., Toroptzova E. M., Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers, Eur. J. Med. Chem., 2006, 41, 1093-1101.
(11) Maruyama T., Kozai S., Shimizu T., Synthesis and hypnotic-sedative activities of N-substituted uracil on mice, Nucleic Acids Research Supplement, 2003, 3, 25-26.
(12) Dramiński M., Frass E., Alkylated derivatives of uracile. Part IX. Synthesis of N-(2,3-dihydroxypropyl)derivatives of 5,6-tetramethyleneuracil, structutral analogs of nucleosides, Polish Journal of Chemistry, 1981, 1547-1552.
(13) Turski K., Nowe pochodne tiazolo[3, 2-a]pirymidyny - potencjalne immunomodulatory, praca doktorska, Łódź, 1992.
(14) Dramiński M., Fiszer B., Alkilowanie pochodnych uracylu. II. Synteza i właściwości N-metylowanych 5-i 5,6-alkilowanych uracyli, Roczniki Chemii Ann. Soc. Chim. Polonorum., 1971, 45, 19-25
Downloads
Published
How to Cite
Issue
Section
Stats
Number of views and downloads: 326
Number of citations: 0