Synthesis of new uracil derivatives and their sugar hydrazones with potent antimicrobial, antioxidant and anticancer activities

References

• Abdel Mohsen, H. T.; Ragab, F. A. F.; Ramla, M. M.; El Diwani, H. I. Novel Benzimidazole–Pyrimidine Conjugates as Potent Antitumor Agents. Eur. J. Med. Chem. 2010, 45, 2336–2344. DOI: 10.1016/j.ejmech.2010.02.011.
   PubMed Web of Science ®Google Scholar
• El-Sayed, W. A.; Abdel-Rahman, A. A.-H.; Ramiz, M. M. M. Anti-Hepatitis B Virus Activity of New N4-β-d-Glycoside Pyrazolo[3,4-d]Pyrimidine Derivatives. Z. Naturforsch. 2009, 64c, 323–328. DOI: 10.1515/znc-2009-5-603.
   Google Scholar
• El-Sayed, W. A.; Rashad, A. E.; Awad, S. M.; Ali, M. M. Synthesis and In Vitro Antitumor Activity of Some New Substituted Thiopyrimidines through Radical Balance Regulation. Nucleosides Nucleotides Nucleic Acids 2009, 28, 261–274. DOI: 10.1080/15257770902946165.
   PubMed Web of Science ®Google Scholar
• El-Sayed, W. A.; Abdel-Rahman, A. A.-H. Copper-Catalyzed Synthesis and Antimicrobial Activity of Disubstituted 1,2,3-Triazoles Starting from 1-Propargyluracils and Ethyl (4-Azido-1,2,3-Trihydroxybutyl)Furan-3-Carboxylate. Z. Naturforsch. 2010, 65B, 57–66. DOI: 10.1515/znb-2010-0110.
   Google Scholar
• Ramez, M. M.; El-Sayed, W. A.; Tantawy, A. A.; Abdel Rahman, A. A.-H. Antimicrobial Activity of New 4,6-Disubstituted Pyrimidine, Pyrazoline, and Pyran Derivatives. Arch. Pharm. Res. 2010, 33, 647–654. DOI: 10.1007/s12272-010-0501-1.
   PubMed Web of Science ®Google Scholar
• Gholap, A. R.; Toti, K. S.; Shirazi, F.; Deshpande, M. V.; Srinivasan, K. V. Efficient Synthesis of Antifungal Pyrimidines via Palladium Catalyzed Suzuki/Sonogashira Cross-Coupling Reaction from Biginelli 3,4-Dihydropyrimidin-2(1H)-Ones. Tetrahedron 2008, 64, 10214–10223. DOI: 10.1016/j.tet.2008.08.033.
   Web of Science ®Google Scholar
• Da, E. P.; Falcao, S.; De Melo, S. J.; Srivastava, R. M.; De, M. T. J.; Catanho, A.; Nascimento, S. C. D. Synthesis and Antiinflammatory Activity of 4-Amino-2-Aryl-5-Cyano-6-{3- and 4-(N-Phthalimidophenyl)} Pyrimidines. Eur. J. Med. Chem. 2006, 41, 276–282.
   PubMed Web of Science ®Google Scholar
• Gillespie, R. J.; Bamford, S. J.; Clay, A.; Gaur, S.; Haymes, T.; Jackson, P. S.; Jordan, A. M.; Klenke, B.; Leonardi, S.; Liu, J.; et al. Antagonists of the Human A2A Receptor. Part 6: Further Optimization of Pyrimidine-4-Carboxamides. Bioorg. Med. Chem. 2009, 17, 6590–6605. DOI: 10.1016/j.bmc.2009.07.078.
   PubMed Web of Science ®Google Scholar
• Eastwood, E. B.; Bissel, A.; Hughes, A. M. 5-Cyano-6-Aryluracil and 2-Thiouracil Derivatives as Potential Chemotherapeuticagents. Encriology 1946, 38, 308–314.
   PubMedGoogle Scholar
• Kreutzberger, A.; Schimmelpfennig, H. Tumour Inhibitoryagents. Part-12: 2-Ureido-4-(3H)-Pyrimidinones. Arch. Pharm. 1981, 314, 34–41. DOI: 10.1002/ardp.19813140107.
   PubMed Web of Science ®Google Scholar
• Ueda, T.; Sakkakibara, J.; Nakagami, J. Synthesis of 5-Amino-4(3H)-Pyrimidinones for Their Analgesic and Anti-Inflammatory Activity. Chem. Pharm. Bull. 1984, 31, 4263–4269. DOI: 10.1248/cpb.31.4263.
   Google Scholar
• Kotwa, R.; Krepelka, J.; Melka, M. Preparation of 5(2-NH2,4 = 0, 6-me, 3,4-Dihydro-5-pyrimidinyl) Pentamides as Neoplasminhibitors. Czech CS 254, 620 (Cl C 07 D 239/47) 15 September1988, Appl. 86/3, 907, Mar 28, 1986, 3 pp.
   Google Scholar
• Atwal, K. Preparation of 2-Amino Dihydropyrimidin-5-Carboxylatesas Cardiovascular Agents. US Patent US 4,769,371 (Cl514-275, C 07 D 239/42), Sep 6, 1988, Appl. 45956, Mar 1, 1987, 14 pp.
   Google Scholar
• Ozeki, K.; Ichikawa, T.; Takehara, H.; Tanimura, K.; Sato, M.; Yaginuma, H. Studies on Antiallergic Agents: synthesis of 2-Anilino-5,6-Dihydro-6-Oxo-5-Pyrimidin-Carboxylic Acid. Chem. Pharm. Bull. 1989, 37, 1780–1787. DOI: 10.1248/cpb.37.1780.
   PubMed Web of Science ®Google Scholar
• Sampath, D.; Rao, V. A.; Plunkett, W. Mechanisms of Apoptosis Induction by Nucleoside Analogs. Oncogene 2003, 22, 9063–9074. DOI: 10.1038/sj.onc.1207229.
   PubMed Web of Science ®Google Scholar
• Carbon, J.; Hung, L.; Jones, D. S. A Reversible Oxidative in Activation of Specific Transfer RNA Species. Proc. Natl. Acad. Sci. USA 1965, 53, 979–986. DOI: 10.1073/pnas.53.5.979.
   PubMed Web of Science ®Google Scholar
• Lipsett, M. N. The Isolation of 4-Thiouridylic Acid from the Soluble Ribonucleic Acid of Escherichia coli. J. Biol. Chem. 1965, 240, 3975–3978.
   PubMed Web of Science ®Google Scholar
• Carbon, J.; David, H.; Studier, M. H. Thiobases in Escherchia coli Transfer RNA: 2-Thiocytosine and 5-Methylaminomethyl-2-Thiouracil. Science 1968, 161, 1146–1147. DOI: 10.1126/science.161.3846.1146.
   PubMed Web of Science ®Google Scholar
• Gauss, D. H.; Sprinzl, M. Compilation of tRNA Sequences. Nucleic Acids Res. 1983, 11, r1–53.
   PubMed Web of Science ®Google Scholar
• Yamada, Y.; Saneyoshi, M.; Nishimura, S.; Ishikura, H. Isolation and Characterization of 2-Thiocytidine from a Serine Transfer Ribonucleic Acid of Escherichia coli. FEBS Lett. 1970, 7, 207–210. DOI: 10.1016/0014-5793(70)80161-2.
   PubMed Web of Science ®Google Scholar
• Ralph, R. K.; Matthews, R. E. F.; Matus, A. I. Effects of 2-Thiouracil on the Formation of Double-Stranded Plant Viral Ribonucleic Acid. Biochim. Biophys. Acta 1965, 108, 53–66. DOI: 10.1016/0005-2787(65)90107-3.
   PubMedGoogle Scholar
• Ruyle, W. V.; Shen, T. Y. Nucleosides. V. 2-Thiopyrimidine-d-Arabinofuranosides. J. Med. Chem. 1967, 10, 331–334. DOI: 10.1021/jm00315a009.
   PubMed Web of Science ®Google Scholar
• Rostkowska, H.; Nowak, M. J.; Lapinski, L.; Bretner, M.; Kulikowski, T.; Leś, A.; Adamowicz, L. Theoretical and Matrix-Isolation Experimental Studies on 2-Thiocytosine and 5-Fluoro-2-Thiocytosine. Biochim. Biophys. Acta 1993, 1172, 239–246. DOI: 10.1016/0167-4781(93)90209-V.
   PubMedGoogle Scholar
• Votruba, I.; Holý, A.; Jošt, K. Conversion of 2-Mercaptopyrimidine into S-(Pyrimidin-2-yl)-Cysteine in Growing Escherichia coli Cells. FEBS Lett. 1972, 22, 287–288. DOI: 10.1016/0014-5793(72)80252-7.
   PubMed Web of Science ®Google Scholar
• Yu, M. Y. W.; Sedaik, J.; Lindsay, R. H. Metabolism of the Nucleoside of 2 Thiouracil (2-Thiouridine) by Rat Liver Slices. Arch. Biochem. Biophys. 1973, 155, 111–758. DOI: 10.1016/S0003-9861(73)80013-X.
   PubMed Web of Science ®Google Scholar
• Holland, J. F.; Guthrie, R.; Sheehe, P.; Tieckelmann, H. Inhibition of Tumor Growth in Mice by a Series of 2-Substituted Thiopyrimidines. Cancer Res. 1958, 18, 776–780.
   PubMed Web of Science ®Google Scholar
• Hamers, R.; Hamers-Casterman, C. Synthesis by Escherichia coli of an Abnormal Beta-Galactosidase in the Presence of Thiouracil. J. Mol. Biol. 1961, 3, 166–170. DOI: 10.1016/s0022-2836(61)80043-0.
   PubMed Web of Science ®Google Scholar
• Albot, J.; Goodgame, D. M. L.; Jeeves, I. The Electronic Structures of Tetrahedral Cobalt(II) Complexes. J. Chem. Soc. Dalton Trans. 1961, 83, 4690–4699. DOI: 10.1021/ja01484a002.
   Google Scholar
• Nassar, I. F.; Atta-Allah, S. R.; Elgazwy, A.-S. S. H. A Convenient Synthesis and Molecular Modeling Study of Novel Pyrazolo[3,4-d]Pyrimidine and Pyrazole Derivatives as Anti-Tumor Agents. J. Enzyme Inhib. Med. Chem. 2015, 30, 396–405. DOI: 10.3109/14756366.2014.940936.
   PubMed Web of Science ®Google Scholar
• Nassar, I. F.; El Farargy, A. F.; Abdelrazek, F. M.; Ismail, N. S. M. Design, Synthesis and Anticancer Evaluation of Novel Pyrazole, Pyrazolo[3,4-d]Pyrimidine and Their Glycoside Derivatives. Nucleosides Nucleoides Nucelic Acids 2017, 36, 275–291. DOI: 10.1080/15257770.2016.1276290.
   PubMed Web of Science ®Google Scholar
• Nassar, I. F.; El Farargy, A. F.; Abdelrazek, F. M. Synthesis and Anticancer Activity of Some New Fused Pyrazoles and Their Glycoside Derivatives. J. Heterocycl. Chem. 2018, 55, 1709–1718. DOI: 10.1002/jhet.3208.
   Web of Science ®Google Scholar
• Nassar, I. F.; Att-Allah, S. R.; Hemdan, M. M. Utility of Thiophene-2-Carbonyl Isothiocyanate as a Precursor for the Synthesis of 1,2,4-Triazole, 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Derivatives with Evaluation of Their Antitumor and Antimicrobial Activities. Phosphorous Sulphur Silicon 2018, 193, 630–636. DOI: 10.1080/10426507.2018.1487435.
   Web of Science ®Google Scholar
• Nassar, I. F.; EL-Kady, D. S.; Awad, H. M.; El-Sayed, W. A. Design, Synthesis, and Anticancer Activity of New Oxadiazolyl-Linked and Thiazolyl-Linked Benzimidazole Arylidines, Thioglycoside, and Acyclic Analogs. J. Heterocyclic Chem. 2019, 56, 1086–1100. DOI: 10.1002/jhet.3496.
   Web of Science ®Google Scholar
• Nassar, I. F.; El-Sayed, W. A.; Ragab, T. I. M.; Shalaby, A. S. G.; Mehany, A. B. M. Design, Synthesis of New Pyridine and Pyrimidine Sugar Compounds as Antagonists Targeting the ERα via Structure-Based Virtual Screening. Mini Rev. Med. Chem. 2019, 19, 395–409. DOI: 10.2174/1389557518666180820125210.
   PubMed Web of Science ®Google Scholar
• Kassem, A. F.; Nassar, I. F.; Abdel Aal, M. T.; Awad, H. M.; El-Sayed, W. A. Synthesis and Anticancer Activity of New ((Furan-2-yl)-1,3,4-Thiadiazolyl)-1,3,4-Oxadiazole Acyclic Sugar Derivatives. Chem. Pharm. Bull. 2019, 67, 888–895. DOI: 10.1248/cpb.c19-00280.
   PubMed Web of Science ®Google Scholar
• Fang, Z.; Li, Y.; Zheng, Y.; Li, X.; Lu, Y.-J.; Yan, S.-C.; Wong, W.-L.; Chan, K.-F.; Wong, K-y.; Sun, N. Antibacterial Activity and Mechanism of Action of a Thiophenyl Substituted Pyrimidine Derivative. RSC Adv. 2019, 9, 10739–10744. DOI: 10.1039/C9RA01001G.
   PubMed Web of Science ®Google Scholar
• Tiwari, O. P.; Tripathi, Y. B. Antioxidant Properties of Different Fractions of Vitex negundo Linn. Food Chem. 2007, 100, 1170–1176. DOI: 10.1016/j.foodchem.2005.10.069.
   Web of Science ®Google Scholar
• Yamaguchi, T.; Takamura, H.; Matoba, T.; Terao, H. Method for Evaluation of the Free Radical-Scavenging Activity of Foods by Using 1,1-Diphe-Nyl-2-Picrylhydrazyl. J. Biosci. Biotechnol. Biochem. 1998, 62, 1201–1204. DOI: 10.1271/bbb.62.1201.
   PubMed Web of Science ®Google Scholar
• Kim, J.-S. Radical Scavenging Capacity and Antioxidant Activity of the E Vitamer Fraction in Rice Bran. J. Food Sci. 2006, 70, C208–213. DOI: 10.1111/j.1365-2621.2005.tb07127.x.
   Web of Science ®Google Scholar
• Badarinath, A. V.; Rao, K. M.; Chetty, C. M. S.; Ramkanth, S.; Rajan, T. V. S.; Gnanaprakash, K. A. Review on In-Vitro Antioxidant Methods: Comparisons. Correlations and Considerations 2010, 2, 1276–1285.
   Google Scholar
• Brand-Williams, W.; Cuvelier, M.; Berset, C. Use of a Free Radical Method to Evaluate Antioxidant Activity. Leb. Wiss. Technol. 1995, 28, 25–30. DOI: 10.1016/S0023-6438(95)80008-5.
   Web of Science ®Google Scholar
• Hansen, M. B.; Nielsen, S. E.; Berg, K. Re-Examination and Further Development of a Precise and Rapid Dye Method for Measuring Cell Growth/Cell Kill. J. Immunol. Methods 1989, 119, 203–210. DOI: 10.1016/0022-1759(89)90397-9.
   PubMed Web of Science ®Google Scholar