Nucleosides 11: synthesis of new derivatives of pyrido[2,3-d]pyrimidines and their nucleosides

References

• Laila, L. M. B.; Mohamed, M. A. M.; Al-Thubaiti, O. A. A.; Elbaih, F. E. M. Nucleoside 10, Synthesis of New Derivatives of Pyrimidine and FusedPyrimidine Nucleosides of Expected Biological Activity. Int. J. Org. Chem. 2019, 9, 85–95. http://www.scirp.org/journal/ijoc.
   Google Scholar
• Guillem, G.; Puig de la Bellacasa, R.; Estrada-Tejedor, R.; Teixidó, J.; Borrell, J. I. Pyrido[2,3-d]Pyrimidin-7(8H)-Ones: Synthesis and Biomedical Applications. Molecules 2019, 24, 4161–4182. DOI: 10.3390/molecules24224161.
   PubMed Web of Science ®Google Scholar
• Abbas, S. E.-S.; George, R. F.; Samir, E. M.; Aref, M. M.; Abdel-Aziz, H. A. Synthesis and Anticancer Activity of Some Pyrido[2,3-d]Pyrimidine Derivatives as Apoptosis Inducers and Cyclin-Dependent Kinase Inhibitors. Future Med. Chem. 2019, 11, 1–20.
   PubMed Web of Science ®Google Scholar
• Furth, P. S.; Reitman, M. S.; Gentles, R.; Cook, A. F. Solid-Phase Synthesis of Novel Amino-Ether Derivatives. Tetrahedron Lett. 1997, 38, 6643–6646. DOI: 10.1016/S0040-4039(97)01579-7.
   Google Scholar
• Furth, P. S.; Reitman, M. S.; Cook, A. F. A Novel Formamidine Linker for Use in Solid-Phase Synthesis. Tetrahedron Lett. 1997, 38, 5403–5406. DOI: 10.1016/S0040-4039(97)01200-8.
   Web of Science ®Google Scholar
• Zhang, F.; Zhao, Y.; Sun, L.; Ding, L.; Gu, Y.; Gong, P. Synthesis and Anti-Tumor Activity of 2-Amino-3-cyano-6-(1H-indol-3-yl)-4-Phenylpyridine Derivatives in Vitro. Eur. J. Med. Chem. 2011, 46, 3149–3157. DOI: 10.1016/j.ejmech.2011.03.055.
   PubMed Web of Science ®Google Scholar
• Kurumurthy, C.; Sambasiva Rao, P.; Veera Swamy, B.; Santhosh Kumar, G.; Shanthan Rao, P.; Narsaiah, B.; Velatooru, L. R.; Pamanji, R.; Venkateswara Rao, J. Synthesis of Novel Alkyltriazole Tagged Pyrido[2,3-d]Pyrimidine Derivatives and Their Anticancer Activity. Eur. J. Med. Chem. 2011, 46, 3462–3468. DOI: 10.1016/j.ejmech.2011.05.011.
   PubMed Web of Science ®Google Scholar
• Abedel Rehim, E. M.; Abd Ellatif, M. Synthesis of Some Novel Pyrido[2,3-d]Pyrimidine and Pyrido[3,2-e] [1,3,4]Triazolo and Tetrazolo[1,5-c]Pyrimidine Derivatives as Potential Antimicrobial and Anticancer Agents. J. Heterocyclic Chem. 2018, 55, 419–430. DOI: 10.1002/jhet.3058.
   Web of Science ®Google Scholar
• Ram, V. J.; Vanden Berghe, D. A.; Vlietinck, A. J. Pyrido[2,3‐d]Pyrimidines and Pyrido[2,3‐d; 5‐d′]Dipyrimidines as Potential Chemotherapeutic Agents. VIII. J Heterocycl. Chem. 1988, 25, 217–219. DOI: 10.1002/jhet.5570250133.
   Web of Science ®Google Scholar
• Piper, J. R.; McCaleb, G. S.; Montgomery, J. A.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. Syntheses and Antifolate Activity of 5-Methyl-5-Deaza Analogues Of Aminopterin, Methotrexate, Folic Acid, and N10-Methylfolic Acid. J. Med. Chem. 1986, 29, 1080–1087. DOI: 10.1021/jm00156a029.
   PubMed Web of Science ®Google Scholar
• Robins, R. K.; Hitchings, G. H. Studies on Condensed Pyrimidine Systems. XIX. A New Synthesis of Pyrido [2,3-d] Pyrimidines. The Condensation of 1,3-Diketones and 3-Ketoaldehydes with 4-Aminopyrimidines. J. Am. Chem. Soc. 1958, 80, 3449–3457. DOI: 10.1021/ja01546a061. DOI: 10.1021/ja01546a061.
   Web of Science ®Google Scholar
• Hasan, M. F.; Madkour, A. M.; Saleem, I.; Rahman, J. M.; Mohammed, E. A. Reactions of 5-(p-Anisyl)-2-Methyl-7-(p-Tolyl)-4H-Pyrido[2,3-d][1,3]-Oxazin-4-One. Heterocycles 1994, 38, 57–69. DOI: 10.3987/COM-91-5873.
   Web of Science ®Google Scholar
• Sako, M. Pyridopyrimidines. Sci. Synth., 2004, 1115–1267. DOI: 10.1055/sos-SD-016-01443.
   Google Scholar
• Gangjee, A.; Adair, O. O.; Queener, S. F. Synthesis and Biological Evaluation of 2,4-Diamino-6-(Arylaminomethyl)Pyrido[2,3-d]Pyrimidines as Inhibitors of Pneumocystis carinii and Toxoplasma gondii Dihydrofolate Reductase and as Antiopportunistic Infection and Antitumor Agents. J. Med. Chem. 2003, 46, 5074–5082. DOI: 10.1021/jm030312n.
   PubMed Web of Science ®Google Scholar
• Elzahabi, H. S. A.; Nossier, E. S.; Khalifa, N. M.; Alasfoury, R. A.; El-Manawaty, M. A. Anticancer Evaluation and Molecular Modeling of Multi-Targeted Kinase Inhibitors Based Pyrido[2,3-d]Pyrimidine Scaffold. J. Enzyme Inhib. Med. Chem. 2018, 33, 546–557. DOI: 10.1080/14756366.2018.1437729.
   PubMed Web of Science ®Google Scholar
• Bergstrom, D. E.; Inoue, H.; Reddy, P. A. Pyrido[2,3-d]Pyrimidine Nucleosides. Synthesis via Cyclization of C-5-Substituted Cytidines. J. Org. Chem. 1982, 47, 2174–2178. DOI: 10.1021/jo00132a038.
   Web of Science ®Google Scholar
• Su, T.-L.; Harada, K.; Watanabe, K. A. Nucleosides. 127. Synthesis of Pyrido[2,3-d]Pyrimidine Nucleosides from 5-Cyanouridine. Nucleosides Nucleotides Nucleic Acids. 1984, 3, 513–524. DOI: 10.1080/07328318408081286.
   Google Scholar
• Kumar, N.; Singh, G.; Yadav, A. K. Of Some New Pyrido[2,3-d]Pyrimidines and Their Ribofuranosides as Possible Antimicrobial Agents. Heteroatom Chem. 2001, 12, 52–56. DOI: 10.1002/1098-1071(2001)12:1 < 52::AID-HC11 > 3.0.CO;2-0.
   Web of Science ®Google Scholar
• Khalafallah, A. K.; Ahmed, M. A. A Novel and Efficient Method for the Synthesis of 6-Amino-Pyrimidine-2(1H)-Thiones Derivatives, Pyrido [2,3-d] Pyrimidine-2(1H)-Thiones Derivatives and Their Glycosides. Chem. Int. 2017, 3, 469–476. http://bosaljournals.com/chemint.
   Google Scholar
• Mosselhi, M. A. N. Nucleoside 1: Ribosylation of 8-Substituted Theophylline Derivatives. Nucleosides Nucleotides Nucleic Acids. 1993, 12, 431–439. DOI: 10.1080/07328319308021213.
   Web of Science ®Google Scholar
• Mosselhi, M. A. N. Nucleosides 2: Synthesis and Properties of 3,4-Diaryl-4,5-Dihydro-1-(β-D-Ribofuranosyl)-1,2,4-Triazole-5-Thiones. Nucleosides Nucleotides Nucleic Acids. 1999, 12, 2043–2049. DOI: 10.1080/0732831990804486.
   Google Scholar
• Mosselhi, M. A. N.; Seliger, H. Nucleosides 3: Synthesis of Novel 1,3,4-Oxadiazole Nucleosides. J. Chem. Res. 2001, 2001, 359–361. DOI: 10.3184/030823401103170278.
   Google Scholar
• Break, L. M.; Shmiss, N. A. M. M.; Mosselhi, M. A. N. Nucleosides 4: Synthesis of Some New S-Nucleoside Derivatives of 2-Thioxo(2,4-Dithioxo)-5,6,7,8-Tetrahydrobenzo-Thieno[2,3-d]Pyrimidin-4-(3H) Ones. Phosphorus Sulfur Silicon Relat. Elem. 2010, 185, 1615–1622. DOI: 10.1080/10426500903147159.
   Web of Science ®Google Scholar
• Mosselhi, M. A. N.; Neidlein, R. Nucleosides 5: Synthesis of Novel 1,2,4-Triazolo [4,3-b]-1,2,4-Triazole Nucleosides. Nucleosides Nucleotides Nucleic Acids. 2009, 28, 1095–1103. DOI: 10.1080/1525777090336837.
   PubMed Web of Science ®Google Scholar
• Metwally, N. H.; Abdalla, M. A.; Mosselhi, M. A. N.; El-Desoky, E. A. Nucleosides 6, Synthesis and Antimicrobial Activity of Some New N-Glycosides of 2-Thioxo-4-Thiazolidinone Derivatives. Carbohydr. Res. 2010, 345, 1135–1141. DOI:10.1016/j.carres.2010.04.01.
   PubMed Web of Science ®Google Scholar
• Mosselhi, M. A. N.; Break, L. M.; Nucleosides, 7. Nucleosides 7(9): Synthesis, Structure, and Biological Activity of New 6-Arylidenamino-2-thio-and 2-Benzylthiopyrimidine N-Nucleosides. Nucleosides Nucleotides Nucleic Acids. 2011, 30, 681–695. DOI: 10.1080/15257770.2011.59762.
   PubMed Web of Science ®Google Scholar
• Break, L. M.; Mosselhi, M. A. N.; Elshafai, N. M. Nucleosides [8]: Ribosylation of Fused Quinazolines: Synthesis of New [1,2,4]Triazolo [5,1-b] and [1,2,4] Triazino [3,2-b]Quinazoline Nucleosides of Fluorescence Interest. J. Chem. 2013, 2013, 1–11. DOI.org/10.1155/2013/612756. DOI: 10.1155/2013/612756.
   Web of Science ®Google Scholar
• Mohamed, M. A. N. M.; Abu-Alola, L. M. B.; Aljaied, N. M. G. Nucleosides 9: Design and Synthesis of New 8-Nitro and 8-Amino Xanthine Nucleosides of Expected Biological Activity. Nucleosides Nucleotides Nucleic Acids. 2017, 36, 745–756. DOI: 10.1080/15257770.2017.1395036.
   PubMed Web of Science ®Google Scholar
• Mosselhi, M. A. N.; Darwish, E.; Peseke, K. Synthesis and Antimicrobial Activity of New Imidazo- and Pyrimido[2,1-f]Theophyllines. Monatsh. Chem. 2008, 139, 825–834. DOI: 10.1007/s00706-008-0854-z.
   Web of Science ®Google Scholar
• Röhrkasten, R.; Raatz, P.; Kreher, R. P.; Blaszkewicz, M. Synthesis of the Caffeine Metabolites 5-Acetylamino-6-Formylamino-3-Methyluracil (AFMU) and 5-Acetylamino-6-Amino-3-Methyluracil (AAMU) on a Preparative Scale. Z. Naturforsch. 1997, 52, 1526–1532. DOI: 10.1515/znb-1997-1214.
   Google Scholar
• Parham, W. E.; Reed, L. J. Ethyethoxymethylene Malonate, Organic Synthesis. Org. Synth. 1948, 28, 60. DOI: 10.15227/orgsyn.028.0060.
   Google Scholar
• Kralj, L.; Hvala, A.; Svete, J.; Golic, L.; Stanovnik, B. Aminoacids in the Synthesis of Heterocyclic Systems. The Synthesis of Methyl 2‐Acetylamino‐3‐Dimethylaminopropenoate and 2‐(N‐Methyl‐N‐Trifluoroacetyl)Amino‐3‐Dimethylaminopropenoate and Their Application in the Synthesis of Heterocyclic Compounds. J. Heterocycl. Chem. 1997, 34, 247–255. DOI: 10.1002/jhet.5570340137.
   Web of Science ®Google Scholar
• Mosselhi, M. A. N. A Convenient Synthesis of Novel Derivatives of Pyrido[2,3-d][1,2,4]-Triazolo[4,3-a]Pyrimidine-5,6-Dione. Monatshefte Fuer Chemie (Chemical Monthly) 2002, 133, 1297–1304. DOI: 10.1007/s00706-002-0469-8.
   Web of Science ®Google Scholar
• Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside Syntheses, XXII1) Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts. Chem. Ber. 1981, 114, 1234–1255. DOI: 10.1002/cber.19811140404.
   Google Scholar