Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 17
194
Views
6
CrossRef citations to date
0
Altmetric
Articles

Synthesis, anticancer activity and molecular docking studies of novel pyrido[1,2-a]pyrimidin-4-one derivatives

, , , &
Pages 2235-2243 | Received 22 Apr 2019, Published online: 30 May 2019

References

  • Jemal, A.; Siegel, R.; Ward, E.; Murray, T.; Xu, J.; Thun, M. J. CA Cancer Statistics. Cancer J. Clin. 2007, 57, 43–66. DOI: 10.3322/canjclin.57.1.43.
  • Eguchi, S. Bioactive Heterocycles; Springer: Berlin, Heidelberg, 2006.
  • Brown, D. J. The Chemistry of Heterocyclic Compounds; Interscience: New York, NY, 1962.
  • Cozzi, P.; Mongelli, N.; Suarato, A. Recent Anticancer Cytotoxic Agents. Curr. Med. Chem. - Anti-Canc. Agent. 2004, 4, 93–121. DOI: 10.2174/1568011043482061.
  • Isanbor, O.; Hagan, D. J. O. Syntheses of Fluorooxindole and 2-Fluoro-2-Arylacetic Acid Derivatives from Diethyl 2-Fluoromalonate Ester. Fluorine Chem. 2006, 12, 303–319. DOI: 10.1016/j.jfluchem.2006.01.011.
  • Nair, V. A.; Mustafa, S. M.; Mohler, M. L.; Fisher, S. J.; Dalton, J. T.; Miller, D. D. Synthesis of Novel Iodo Derived Bicalutamide Analogs. Tetrahedron Lett. 2004, 45, 9475–9477. DOI: 10.1016/j.tetlet.2004.10.130.
  • Ohtsu, H.; Xiao, Z.; Ishida, J.; Nagai, M.; Wang, H. K.; Itokawa, H.; Su, C. Y.; Shih, C.; Chiand, T.; Chang, E.; et al. Curcumin Analogues as Novel Androgen Receptor Antagonists with Potential as anti-Prostate Cancer Agents. J. Med. Chem. 2002, 45, 5037–5042. DOI: 10.1021/jm020200g.
  • Maley, G. F.; Maley, F. Properties of a Defined Mutant of Escherichia coli Thymidylate Synthase. J. Biol. Chem. 1988, 263, 7620–7627.
  • Degraw, J. I.; Tagawa, H.; Christie, P. H.; Lawson, J. A.; Brown, E. G.; Kisliuk, R. L.; Gaumont, Y. Synthesis of 5,10‐Dideazaminopterin. J. Heterocycl. Chem. 1986, 23, 1–4. DOI: 10.1002/jhet.5570230101.
  • Sharma, R.; Goyal, R. D.; Prakash, L. Synthesis of 5,7-disubstituted Pyrido[2,3-d]pyrimidine Derivatives and their Antibacterial Activity. Indian J. Chem. 1992, 31B, 719.
  • Singh, G.; Singh, G.; Yadav, A. K.; Mishra, A. K. Synthesis of Some Novel 4-Imino-3,5,7-Trisubstituted Pyrido[2,3-d]Pyrimidine-2(1H)-Thiones and Their Nucleosides as Potential Therapeutic Agents. Phosphorus and Sulfur Silicon and Related Elements 2000, 165, 107. DOI: 10.1080/10426500008076330.
  • Agrafoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Synthesis of Carbocyclic Nucleosides. Tetrahedron 1994, 50, 10611–10670. DOI: 10.1016/S0040-4020(01)89258-9.
  • Suzuki, S.; Isono, K.; Nagtsu, J.; Kawashina, Y.; Yamagata, Y.; Sasaki, K.; Hashimoto, K. Studies on Polyoxins, Antifungal Antibiotics: Part IV Isolation of Polyoxins C, D, E, F and G, New Components of Polyoxin Complex. Agric. Biol. Chem. 1996, 30, 814–817. DOI: 10.1021/jf00106a033.
  • Makishima, I.; Honma, Y.; Hozumi, M.; Sampim, K.; Hatorri, K.; Ogura, H.; Motoyoshi, K. Exp Hematol. 1993, 20, 51845.
  • Robbins, R. K.; Srivastava, P. C.; Narayanan, V. L.; Plowman, J.; Paull, K. D. 2-beta-D-Ribofuranosylthiazole-4-Carboxamide, a Novel Potential Antitumor Agent for Lung Tumors and Metastases. J. Med. Chem. 1982, 25, 107–108. DOI: 10.1021/jm00344a002.
  • Focher, F.; Ubiali, D.; Pregnolato, M. Nucleosides and Nucleotides. 152. 1-(3-C-Ethynyl-β-D-Ribo-Pentofuranosyl) Uracil as a Broad Spectrum Antitumor Nucleoside. Bioorg. Med. Chem. Lett. 1996, 6, 1887. DOI: 10.1016/0960-894X(96)00339-3.
  • Gossett, L. S.; Shih, C. Pyridoprimidine derivatives as antineoplastic agents. Eur. Patent Appl. EP 511,792 (C1.CO7D471/104) (1992) U.S. Patent Appl., 1991.
  • Bozing, D.; Benko, P.; Petocz, L.; Szecsey, M.; Toempe, P.; Gingler, G. NYA Kinoxalin-1,4-Dioxidderivat. Eur. Patent Appl. EP, 1991.
  • Nishikawa, Y.; Shindo, T.; Ishii, K.; Nakamura, H.; Kon, T.; Uno, H.; Matsumoto, J. Synthesis and Antiallergic Activity of N-[4-(4-Diphenylmethyl-1-Piperazinyl)Butyl]-1,4-Dihydro-4-Oxopyridine-3 - Carboxamides. Chem. Pharm. Bull. 1989, 37, 1256. DOI: 10.1248/cpb.37.1256.
  • Hhigh, D.; Rami, H. K.Benzoxazoles and Pryridine Derivatives useful in the Treatment of the Type II Diabetes. Int PCT. Int. Appl. WO 9604261 [Chem. Abstr.], 1996.
  • Pai, S. B.; Liu, S. H.; Zhu, Y. L.; Chu, C. K.; Cheng, Y. C. Inhibition of Hepatitis B Virus by a Novel L-Nucleoside, 2′-Fluoro-5-Methyl-beta-L-Arabinofuranosyl Uracil. Antimicrob. Agents Chemother. 1996, 40, 380. DOI: 10.1128/AAC.40.2.380.
  • Neuwmann, R.; Morten, R. Drugs Today 1998, 21, 13.
  • Robin, R. K. Chem. Eng. News 1928, 28.
  • Verheggen, I.; Van Aerschot, A.; Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; De Clercq, E.; Herdewijn, P. Synthesis and Antiherpes Virus Activity of 1,5-Anhydrohexitol Nucleosides. J. Med. Chem. 1993, 36, 2033–2040. DOI: 10.1021/jm00066a013.
  • Stoltefuss, J.; Boeshagen, H.; Schramm, M.; Thomas, G. Chem. Abstr. 1984, 101, 55110v.
  • Geroffen, D. E.; Bayer, A. G. Chem. Abstr. 1984. 101, 3234684.
  • Baraldi, P. G.; Cacciari, B.; Romagnoli, R.; Spalluto, G.; Monopoli, A.; Ongini, E.; Varani, K.; Borea, P. A. 7-Substituted 5-Amino-2-(2-Furyl)Pyrazolo[4,3-e]-1,2,4-Triazolo[1,5-c]Pyrimidines as A2A Adenosine Receptor Antagonists: A Study on the Importance of Modifications at the Side Chain on the Activity and Solubility. J. Med. Chem. 2002, 45, 115–126. DOI: 10.1021/jm010924c.
  • Goodacre, S. C.; Street, L. J.; Hallett, D. J.; Crawforth, J. M.; Kelly, S.; Owens, A. P.; Blackaby, W. P.; Lewis, R. T.; Stanley, J.; Smith, A. J.; et al. Imidazo[1,2-a]Pyrimidines as Functionally Selective and Orally Bioavailable GABA(A)alpha2/alpha3 Binding Site Agonists for the Treatment of Anxiety Disorders. J. Med. Chem. 2006, 49, 35–38. DOI: 10.1021/jm051065l.
  • Chen, C.; Wilcoxen, K. M.; Huang, C. Q.; Xie, Y. F.; McCarthy, J. R.; Webb, T. R.; Zhu, Y. F.; Saunders, J.; Liu, X. J.; Chen, T. K.; et al. Design of 2,5-Dimethyl-3-(6-Dimethyl-4-Methylpyridin-3-yl)-7-di Propylaminopyrazolo [1,5-a] Pyrimidine (NBI 30775/R121919) and Structure-Activity Relationships of a Series of Potent and Orally Active Corticotropin-Releasing Factor Receptor Antagonists. J. Med. Chem. 2004, 47, 4787–4798. DOI: 10.1021/jm040058e.
  • Akhtar, T.; Hameed, S.; Khan, K. M.; Khan, A.; Choudhary, M. I. Design, Synthesis, and Urease Inhibition Studies of Some 1,3,4-Oxadiazoles and 1,2,4-Triazoles Derived from Mandelic Acid. J. Enzyme Inhib. Med. Chem. 2010, 25, 572–576. DOI: 10.3109/14756360903389864.
  • Gautham, S. K.; Gaddameedi, J. D.; Nagiri, R. K.; Desireddy, K. S.; Yedla, P. C.; Chityala, G. K.; Banda, N. Synthesis of Novel Pyrido [1,2-a] Pyrimidine-3-Carboxamide Derivatives and Their anti-Cancer Activity. Chem. Pharm. Bull. 2015, 63, 584–590. DOI: 10.1248/cpb.c15-00219.
  • Santhosh Kumar, G.; Poornachandra, Y.; Ratnakar Reddy, K.; Ganesh Kumar, C.; Narsaiah, B. Synthesis of Novel Triazolothione, Thiadiazole, Triazole-Functionalized Furo/Thieno[2,3-b]Pyridine Derivatives and Their Antimicrobial Activity. Syn. Comm. 2017, 47, 1864–1873. DOI: 10.1080/00397911.2017.1354379.
  • Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: application to Proliferation and Cytotoxicity Assays. J. Immunol. Meth. 1983, 65, 55–63. DOI: 10.1016/0022-1759(83)90303-4.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.