Novel 5-arylcarbamoyl-2-methylisoxazolidin-3-yl-3-phosphonates as nucleotide analogues

Nucleosides, Nucleotides and Nucleic Acids

Volumn 33, Issue 8, 2014, Pages 552-582

  Kokosza, Kamil ^a   Balzarini, Jan ^b   Piotrowska, Dorota G ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

1 3 dipolar cycloaddition; isoxazolidines; Modified nucleosides; phosphonates

Indexed keywords

ACRYLAMIDE DERIVATIVE; DIETHYL CIS 5 (5 METHYLPYRIDIN 2 YLCARBAMOYL) 2 METHYLIS OXAZOLIDIN 3 YL 3 PHOSPHONATE CIS; DIETHYL TRANS 5 (2,5 DIHYDRO 2,3 DIMETHYL 5 OXO 1 PHENYL 1 H PYRAZOL 4 YLCARBAMOYL) 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (4 METHOXY 6 METHYLPYRIMIDIN 2 YLCARBAMOYL) 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (4 METHYLPYRIDIN 2 YLCARBAMOYL) 2 METHYLIS OXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (4 METHYLPYRIMIDIN 2 YLCARBAMOYL) 2 METHYLIS OXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (4,6 DIMETHOXYPYRIMIDIN 2 YLCARBAMOYL) 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (5 METHYLPYRIDIN 2 YLCARBAMOYL) 2 METHYLIS OXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (PYRIDIN 2 YLCARBAMOYL) 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 (PYRIMIDIN 2 YLCARBAMOYL) 2 METHYLISOXAZOLIDIN 3YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 [1 (TERT BUTOXYCARBONYL) 1 H PYRAZOL 3 YLCARBAMOYL] 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; DIETHYL TRANS 5 [1 (TERT BUTOXYCARBONYL) 5 METHYL 1 H PYRAZOL 3 YLCARBAMOYL] 2 METHYLISOXAZOLIDIN 3 YL 3 PHOSPHONATE TRANS; N (1 H INDOL 5 YL)ACRYLAMIDE; N (1 H INDOL 6 YL)ACRYLAMIDE; N (1,3 DIOXOISOINDOLIN 5 YL)ACRYLAMIDE; N (2 METHYL 1 H INDOL 5 YL)ACRYLAMIDE; N (4 METHOXY 6 METHYLPYRIMIDIN 2 YL)ACRYLAMIDE; N (4 METHYLPYRIDIN 2 YL)ACRYLAMIDE; N (4 METHYLPYRIMIDIN 2 YL)ACRYLAMIDE; N (4,6 DIMETHOXYPYRIMIDIN 2 YL)ACRYLAMIDE; N (PYRAZIN 2 YL)ACRYLAMIDE; N (THIAZOL 2 YL)ACRYLAMIDE; N [1 H BENZO (DEXTRO )IMIDAZOL 6 YL]ACRYLAMIDE; N [2,2 DIFLUOROBENZO(DEXTRO) (1,3) DIOXOL 5 YL]ACRYLAMIDE; N [5 ACETYLBENZO(DEXTRO) (1,3) DIOXOL 6 YL)ACRYLAMIDE; OXAZOLIDINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TERT BUTYL 3 (ACRYLAMIDO) 1 H PYRAZOLE 1 CARBOXYLATE; TERT BUTYL 3 (ACRYLAMIDO) 5 METHYL 1 H PYRAZOLE 1 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; ISOXAZOLE DERIVATIVE; NUCLEOTIDE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLOADDITION; CYTOSTASIS; DNA VIRUS; DRUG SCREENING; FEMALE; HELA CELL LINE; HUMAN; HUMAN CELL; IC 50; NONHUMAN; RNA VIRUS; STEREOCHEMISTRY; STEREOISOMERISM; CHEMISTRY; DRUG EFFECTS; IC50; SYNTHESIS; TOXICITY; TUMOR CELL LINE; VIRUS;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; HUMANS; INHIBITORY CONCENTRATION 50; ISOXAZOLES; NUCLEOTIDES; VIRUSES;

EID: 84904503611     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2014.909046     Document Type: Article

References (54)

1. Williams, J.D; Khan, A.R.; Harden, E.A.; Hartline, C.B.; Jefferson, G.M.; Keith, K.A.; Prichard, M.N.; Zemlicka, J.; Peet, N.P.; Bowlin, T.L. Synthesis and antiviral activity of certain second generation methylenecyclopropane nucleosides. Bioorg. Med. Chem. 2012, 20, 3710-3718.
2. Rios Morales, E.H.; Balzarini, J.; Meier, C. Stereoselective synthesis and antiviral activity of methylsubstituted cyclosal-pronucleotides. J. Med. Chem. 2012, 55, 7245-7252.
3. Agarwal, H.K.; Chhikara, B.S.; Hanley, M. J; Ye, G.; Doncel, G.F.; Parang, K. Synthesis and biological evaluation of fatty acyl ester derivatives of (?)-2-, 3-dideoxy-3-thiacytidine. J. Med. Chem. 2012, 55, 4861-4871.
4. Ikeuchi, H.; Ahn, Y.-M.; Otokawa, T.; Watanabe, B.; Hegazy, L.; Hiratake, J.; Richards, N.G. J. A su lfoximine-based inhibitor of human asparagine synthetase kills L-asparaginase-resistant leukemia cells. Bioorg. Med. Chem. 2012, 20, 5915-5927.
5. Choi, W.J.; Chung, H.-J.; Chandra, G.; Alexander, V.; Zhao, L.X.; Lee, H.W.; Nayak, A.; Majik, M.S.; Kim, H.O.; Kim, J.-H.; Lee, Y.B.; Ahn, C.H.; Lee, S.K.; Jeong, L.S. Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity. J. Med. Chem. 2012, 55, 4521-4525.
6. Bosc, J.-J.; Latxague, L.; Ĺeger, J.-M.; Balzarini, J.; Forfar, I.; Jarry, C.; Guillon, J. Synthesis and in vitro cytostatic activity of new β-D-arabino-furan[1-, 2-:4, 5]oxazolo-and arabino-pyrimidinone derivatives. Eur. J. Med. Chem. 2010, 45, 831-839.
7. Krim, J.; Gr̈unewald, C.; Taourirte, M.; Engels, J.W. Efficient microwave-assisted synthesis, antibacterial activity and high fluorescence of 5 benzimidazolyl-2-deoxyuridines. Bioorg. Med. Chem. 2012, 20, 480-486.
8. Matyugina, E.; Khandazhinskaya, A.; Chernousova, L.; Andreevskaya, S.; Smirnova, T.; Chizhov, A.; Karpenko, I.; Kochetkov, S.; Alexandrova, L. The synthesis and antituberculosis activity of 5-nor carbocyclic uracil derivatives. Bioorg. Med. Chem. 2012, 20, 6680-6686.
9. Srivastav, N.C.; Shakya, N.; Bhavanam, S.; Agrawal, A.; Tse, C.; Desroches, N.; Kunimoto, D.Y.; Kumar, R. Antimycobacterial activities of 5-alkyl (or halo)-3-substituted pyrimidine nucleoside analogs. Bioorg. Med. Chem. Lett. 2012, 22, 1091-1094.
10. Hockov́a, D.; Keough, D.T.; Janeba, Z.; Wang, T.-H.; de Jersey, J.; Guddat, L.W. Synthesis of novel Nbranched acyclic nucleoside phosphonates as potent and selective inhibitors of human, plasmodium falciparum and plasmodium vivax 6-oxopurine phosphoribosyltransferases. J. Med. Chem. 2012, 55, 6209-6223.
11. Romeo, G.; Chiacchio, U.;Corsaro, A.; Merino, P.Chemical synthesis of heterocyclic-sugar nucleoside analogues. Chem. Rev. 2010, 110, 3337-3370.
12. Ichikawa, E.; Kato, K. Sugar-modified nucleosides in past 10 years, a review. Curr. Med. Chem. 2001, 8, 385-423. (Pubitemid 32409787)
13. Shelton, J.R.; Cutler, C.E.; Oliveira, M.; Balzarini, J.; Peterson, M.A. Synthesis, SAR, and preliminary mechanistic evaluation of novel antiproliferative N6, 5-bis-ureido-and 5-carbamoyl-N6-ureidoadenosine derivatives. Bioorg. Med. Chem. 2012, 20, 1008-1019.
14. Verma, V.A.; Rossman, R.; Bennett, F.; Chen, L.; Gavalas, S.; Girijavallabhan, V.; Huang, Y.; Kim, S.-H.; Kosinski, A.; Pinto, P.; Rizvi, R.; Shankar, B.; Tong, L.; Velazquez, F.; Venkatraman, S.; Kozlowski, J.; MacCoss, M.; Kwong, C.D.; Bansal, N.; Kezar III, H.S.; Reynolds, R.C.; Maddry, J.A.; Ananthan, S.; Secrist III, J.A.; Li, C.; Chase, R.; Curry, S.; Huang, H.-C.; Tong, X.; Njoroge, F.G.; Arasappan, A. Synthesis and SAR of geminal substitutions at the C5-carbosugar position of pyrimidine-derived HCV inhibitors. Bioorg. Med. Chem. Lett. 2012, 22, 6967-6973.
15. Manfredini, S.; Solaroli, N.; Angusti, A.; Nalin, F.; Durini, E.; Vertuani, S.; Pricl, S.; Ferrone, M.; Spadari, S.; Focher, F.; Verri, A.; De Clercq, E.; Balzarini, J. Design and synthesis of phosphonoacetic acid (PPA) ester and amide bioisosters of ribofuranosylnucleoside diphosphates as potential ribonucleotide reductase inhibitors and evaluation of their enzyme inhibitory, cytostatic and antiviral activity. Antivir. Chem. Chemother. 2003, 14, 183-194. (Pubitemid 37267733)
16. Sargsyan, G.; MacLeod, B.L.; Tohgha, U.; Balaz, M. Sequence and linker dependent chiral dimerization of DNA-porphyrin conjugates. Tetrahedron 2012, 68, 2093-2099.
17. Tosh, D.K.; Phan, K.; Gao, Z.-G.; Gakh, A.A.; Xu, F.; Deflorian, F.; Abagyan, R.; Stevens, R.C.; Jacobson, K.A.; Katritch, V. Optimization of adenosine 5-carboxamide derivatives as adenosine receptor agonists using structure-based ligand design and fragment screening. J. Med. Chem. 2012, 55, 4297-4308.
18. Hausler, N.E.; Devine, S.M.; McRobb, F.M.; Warfe, L.; Pouton, C.W.; Haynes, J.M.; Bottle, S.E.; White, P.J.; Scammells, P.J. Synthesis and pharmacological evaluation of dual acting antioxidant A2A adenosine receptor agonists. J. Med. Chem. 2012, 55, 3521-3534.
19. Diab, S.A.; De Schutter, C.; Muzard, M.; Plantier-Royon, R.; Pfund, E.; Lequeux, T. Fluorophosphonylated nucleoside derivatives as new series of thymidine phosphorylase multisubstrate inhibitors. J. Med. Chem. 2012, 55, 2758-2768.
20. Chaudhary, P.M.; Chavan, S.R.; Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S.P.; Likhite, A.P.; Gonnade, R.; Hazara, B.G.; Deshpande, M.V.; Deshpande, S.R. Exploration of click reaction for the synthesis of modified nucleosides as chitin synthase inhibitors. Bioorg. Med. Chem. 2009, 17, 2433-2440.
21. Park, S.M.; Yang, H.; Park, S.-K.; Kim, H.M.; Kim, B.H. Design, synthesis, and anticancer activities of novel perfluoroalkyltriazole-appended 2-deoxyuridines. Bioorg. Med. Chem. Lett. 2010, 20, 5831-5834.
22. Lee, Y.-S.; Park, S.M.; Kim, H.M.; Park, S.-K.; Lee, K.; Lee, C.W.; Kim, B.H. C5-Modified nucleosides exhibiting anticancer activity. Bioorg. Med. Chem. Lett. 2009, 19, 4688-4691.
23. Galmarini, C.M.; Mackey, J.R.; Dumontet, C. Nucleoside analogues and nucleobases in cancer treatment. Lancet Oncol. 2002, 3, 415-4424.
24. De Clercq, E. Highlights in the discovery of antiviral drugs: A personal retrospective. J. Med. Chem. 2010, 53, 1438-1450.
25. Hecker, S.J.; Erion, M.D. Prodrugs of phosphates and phosphonates. J. Med. Chem. 2008, 51, 2328-2345. (Pubitemid 351628494)
26. De Clercq, E. Antiretroviral drugs. Curr. Opin. Pharmacol. 2010, 10, 507-515.
27. Arimilli, M.N.; Kim, C.U.; Dougherty, J.; Mulato, A.; Oliyai, R.; Shaw, J.P.; Cundy, K.C.; Bischofberger, N. Synthesis, in vitro biological evaluation and oral bioavailability of 9-[2-(phosphonomethoxy)propyl]adenine (PMPA) prodrugs. Antiviral Chem. Chemother. 1997, 8, 557-564. (Pubitemid 27504721)
28. Sorbera, L.A.; Serradell, N.; Bolos, J. Pradefovir mesilate treatment of hepatitis B. Drugs Future 2007, 32, 137-143.
29. Harris, S.A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Synthesis and antiviral evaluation of phosphoramidate derivatives of (E)-5-(2-bromovinyl)-2-deoxyuridine. Antiviral Chem. Chemother. 2001, 12, 293-300. (Pubitemid 34168777)
30. Tronchet, J.M.J.; Iznaden, M.; Barbalat-Rey, F.; Dhimane, H.; Ricca, A.; Balzarini, J.; De Clercq, E. Isoxazolidine analogs of nucleosides. Eur. J. Med. Chem. 1992, 27, 555-560.
31. Chiacchio, U.; Corsaro, A.; Iannazzo, D.; Piperno, A.; Pistar̀a, V.; Rescifina, A.; Romeo, R.; Valveri, V.; Mastino, A.; Romeo, G. Enantioselective syntheses and cytotoxicity of N, O-nucleosides. J. Med. Chem. 2003, 46, 3696-3702.
32. Bortolini, O.; De Nino, A.; Eliseo, T.; Gavioli, R.; Maiuolo, L.; Russo, B.; Sforza, F. Synthesis and biological evaluation of diastereoisomerically pure N, O-nucleosides. Bioorg. Med. Chem. 2010, 19, 6970-6976.
33. Chiacchio, U.; Balestrieri, E.; Macchi, B.; Iannazzo, D.; Piperno, A.; Rescifina, A.; Romeo, R.; Saglimbeni, M.; Sciortino, M.T.; Valveri, V.; Mastino, A.; Romeo, G. Synthesis of phosphonated carbocyclic 2-Oxa-3-aza-nucleosides: Novel inhibitors of reverse transcriptase. J. Med. Chem. 2005, 48, 1389-1394.
34. Piotrowska, D.G. N-Substituted C-diethoxyphosphorylated nitrones as useful synthons for the synthesis of α-aminophosphonates. Tetrahedron Lett. 2006, 47, 5363-5366. (Pubitemid 43949210)
35. Piotrowska, D.G. Stereochemistry of substituted isoxazolidines derived from N-methyl Cdiethoxyphosphorylated nitrone. Tetrahedron 2006, 62, 12306-12317. (Pubitemid 44773770)
36. Piperno, A.; Giofr̀e, S.V.; Iannazzo, D.; Romeo, R.; Romeo, G.; Chiacchio, U.; Rescifina, A.; Piotrowska, D.G. Synthesis of C-4-Truncated phosphonated carbocyclic 2-Oxa-3-azanucleosides as antiviral agents. J. Org. Chem. 2010, 75, 2798-2805.
37. Piotrowska, D.G.; Ciéslak, M.; Kŕolewska, K.; Wŕoblewski, A.E. Design, Synthesis and cytotoxicity of a new series of isoxazolidine based nucleoside analogues. Arch. Pharm. Chem. Life Sci. 2011, 11, 301-310.
38. Romeo, R.; Carnovale, C.; Giofr?c, S.V.; Romeo, G.; Macchi, B.; Frezza, C.; Marino-Merlo, F.; Pistaŕr, V.; Chiacchio, U. Truncated phosphonated C-1-branched N, O-nucleosides: A new class of antiviral agents. Bioorg. Med. Chem. 2012, 20, 3652-3657.
39. Piotrowska, D.G.; Balzarini, J.; Głowacka, I.E. Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a 1, 2, 3-triazole linker. Eur. J. Med. Chem. 2012, 47, 501-509.
40. Kokosza, K.; Balzarini, J.; Piotrowska, D.G. Design, synthesis, antiviral and cytostatic evaluation of novel isoxazolidine nucleotide analogues with a carbamoyl linker. Bioorg. Med. Chem. 2013, 21, 1097-1108.
41. Francis, A.W.; Helquist, S.A.; Kool, E.T.; David, S.S. Probing the requirements for recognition and catalysis in Fpg and MutY with nonpolar adenine isosteres. J. Am. Chem. Soc. 2003, 125, 16235-16242. (Pubitemid 38020648)
42. Kool, E.T.; Morales, J.C.; Guckian, K.M. Mimicking the structure and function of DNA: Insights into DNA stability and replication. Angew. Chem. Int. Ed. 2000, 39, 990-1009. (Pubitemid 30217233)
43. Kool, E.T. Active site tightness and substrate fit in DNA replication. Annu. Rev. Biochem. 2002, 71, 191-219. (Pubitemid 34800219)
44. Stambasḱy, J.;Hocek, M.; Ko?covsḱy, P. C-Nucleosides: Synthetic strategies and biological applications. Chem. Rev. 2009, 109, 6729-6764.
45. Henwood, J.M.; Brogden, R.N. Etoposide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in combination chemotherapy of cancer. Drugs 1990, 39, 438-490.
46. Stewart, D.J.; Richard, M.T.; Hugenholtz, H.;Dennery, J.; Nundy, D.; Prior, J.; Montpetit, V.;Hopkins, H.S. Penetration of teniposide (VM-26) into human intracerebral tumors. J. Neurooncol. 1984, 2, 315-324.
47. White, P.W.; Titolo, S.; Brault, K.; Thauvette, L.; Pelletier, A.; Welchner, E.; Bourgon, L.; Doyon, L.; Ogilvie, W.W.; Yoakim, C.; Cordingley, M.G.; Archambault, J. Inhibition of human papillomavirus DNA replication by small molecule antagonists of the E1-E2 protein interaction. J. Biol. Chem. 2003, 278, 26765-26772. (Pubitemid 36876824)
48. Ferńandez, F.; Garć?a-Mera, X.; Rodŕ?guez, G.; Urrutia, A. New hexahydrocarbazoles and spiro indoles, and their affinity for D2 dopamine and 5-HT2A serotonin receptors. Chem. Pharm. Bull. 1999, 47, 1006-1009. (Pubitemid 29357383)
49. Honma, T.; Yoshizumi, T.; Hashimoto, N.; Hayashi, K.; Kawanishi, N.; Fukasawa, K.;Takaki, T.; Ikeura, C.; Ikuta, M.; Suzuki-Takahashi, I.; Hayama, T.; Nishimura, S.; Morishima, H.A Novel Approach for the development of selective Cdk4 inhibitors: Library design based on locations of Cdk4 specific amino acid residues. J. Med. Chem. 2001, 44, 4628-4640. (Pubitemid 33144472)
50. Karplus, M. Vicinal proton coupling in nuclear magnetic resonance J. Am. Chem. Soc. 1963, 85, 2870-2871.
51. Benezra, C., The variation of vicinal 31P-C-C-1H couplings with dihedral angle in phosphonates C. J. Am. Chem. Soc. 1973, 95, 6890-6894.
52. Neeser J.-R.; Tronchet, J.M.J.; Charollais, E.J. Structural analysis of 3-C-phosphonates,-phosphinates, and-phosphine oxides of branched-chain sugars Can. J. Chem. 1983, 61, 2112-2120.
53. Adiwidjaja, G.; Meyer, B.; Thiem, J. Synthesis and crystal structure of endo-2-dimethylphosphono-exo-2-hydroxy-(?)-camphane for the determination of 3J (CCCP) vicinal coupling constants, Z. Naturforsch 1979, 34b, 1547-1551.
54. Buchanan, G.W.; Bourque, K.; Seeley, A. 13C and 31P NMR spectra of 1-diethylphosphono-1-hydroxycycloalkanes Magn. Res. Chem. 1986, 24, 360-367.