An in vitro assessment of the antineoplastic potential of 2H-1,3-Oxazine-2,6(3H)-dione (3-oxauracil), a novel pyrimidine

Abstract

The pyrimidine (uracil) analogue 3-oxauracil (OU) previously had been shown to completely inhibit the growth of E. coli B and decrease by 96% the replication of herpes simplex virus type 2 when present in the culture fluid at a concentration of 10(2) microM. Limited in vivo studies in mice demonstrated antiviral effects without significant toxicity when given i.p. daily for two weeks at a concentration of 3.23 mg/kg. However, the antineoplastic properties of OU were unknown. We assessed the ability of OU to inhibit the proliferation of various human tumor cell lines (3 pancreatic, 1 colon, 1 neuroendocrine, and 1 lung) in an in vitro radiometric (Bactec) system. In the pancreatic lines (RWP-2, MiaPaCa-2, and PANC-1), the colon line (HT-29), the neuroendocrine line (COLO 320DM), and the lung cancer cell line (SK-MES-1), OU at a concentration of 10(3) microM, produced a dramatic decrease in percent cell survival. When compared with cytotoxic drugs of choice for these tumor cells (gemcitabine, 5-fluorouracil, and adriamycin, respectively) a significantly higher concentration of OU was required usually to achieve comparable results with two exceptions. These were the HT-29 and the COLO 320DM cell lines. These results indicate OU has significant (p < 0.05) cytotoxic activity against pancreatic, colon, neuroendocrine, and nonsmall cell lung cancer lines, when compared to untreated control cultures. Additional in vivo testing of this potential antineoplastic agent is warranted.

Aryl Chalcones as Efficient Precursors for Deriving Oxazine: Solvent-Free Synthesis and Antimicrobial Activities of some Oxazine-2-amines

“…The AVATAR-300 Fourier transform spectrophotometer was used for recording infrared spectra (KBr, 4000-400 cm -1 ) of all oxazines in KBr disc. The Bruker AV400 series type NMR spectrometer was utilized for recording NMR spectra of all oxazines, operating at 400 MHz for 1 H and100 MHz for 13 C spectra in CDCl 3 solvent using TMS as internal standard. Mass spectra of all synthesised oxazines were recorded on SHIMADZU mass spectrometer using chemical ionization technique.…”

“…The important medicinal activities of these oxazines are anti-bacterial [2][3][4], anti-fungal [2][3][4], antiplasmodial [5], anti-cancer [6], anti-depressants [7], cytotoxicity [8], anti-osteoplastic [9], anti-tumour [10], anti-oxidant [11], anti-tuberculosis [12], anti-neoplastic [13], antagonists [14], anti-inflammatory [15], anti-infectants [16], IKB kinase beta [17] and PTP-1B inhibition [18].…”

SOLID SiO2-H3PO4 IS AN EFFICIENT CATALYST FOR CYCLIZATION OF ENONES UNDER SOLVENT-FREE CONDITION: SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF SOME OXAZINE DERIVATIVES

“…These oxazines were medicinally important due to the presence of oxygen, nitrogen heteroatoms along with a double bonds in their structural moieties 3 . The important medicinal activities of these oxazines are anti-bacterial, antifungal [3][4][5] , anti-plasmodial 6 , anti-cancer 7 , anti-depressants 8 , cytotoxicity 9 , anti-osteoplastic 10 , anti-tumour 11 , anti-oxidant 12 , anti-tuberculosis 13 , antineoplastic 14 , antagonists 15 , anti-inflammatory 16 , anti-infectants 17 , IKB kinase beta 18 and PTP-1B inhibition 19 . These oxazine derivatives were applied for improving the super resolution microscope 20 , synthesis of eosinophils 21 , identification and separation of neutrophils 22 .…”

Infrared and NMR Spectral Hammett Correlations in 4-(2-Naphthyl)-5,6-Dihydro-6-(Substituted Phenyl)-⁴H-1,3-Oxazine-2-Amines

“…The unsaturated cyclic oxazine-2-amines are important bioactive molecules. They possess many biologically activities such as antimicrobial [9], anti-plasmodial [10], anti-cancer [11], anti-depressants [12], cytotoxicity [13], anti-osteoplastic [14], anti-tumour [15], anti-oxidant [16], anti-tuberculosis [17], anti-neoplastic [18], antagonists [19], antiinflammatory [20] anti-infectants [21], IKB kinase beta [22], PTP-1B inhibition [23] and insect antifeedant activities [24].…”