Stereospecific deuteration of α-furanosyl azomycin nucleosides: A model reaction for tritium radiolabeling

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 11, 2008, Pages 3256-3260

  Kumar, Piyush ^a   Emami, Saeed ^b   McEwan, Alexander J B ^a   Wiebe, Leonard I ^a,b  

^a CROSS CANCER INSTITUTE   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Azomycin nucleosides; FAZA; PET radiodiagnostics; Stereospecific deuteration; Tumor hypoxia

Indexed keywords

1 ALPHA DEXRO(2' DEUTEREORIBOFURANOSYL) 2 NITROIMIDAZOLE; 1 ALPHA DEXTRO (3',5' O,O TETRAISOPROPYLDISILYLOXY 2' DEUTERORIBOFURANOSYL) 2 NITROIMIDAZOLE; 1 ALPHA DEXTRO (3',5' O,O TETRAISOPROPYLDISILYLOXY 2' KETO RIBOFURANOSYL) 2 NITROIMIDAZOLE; 1 ALPHA DEXTRO (3',5' O,O TETRAISOPROPYLDISILYLOXYARABINOFURANOSYL) 2 NITROIMIDAZOLE; 2 HYDROXYMETHYL 3A DEUTERO 2,3,8A TRIHYDROFUROL[2,3 D]IMIDAZOLO[2,1 B]OXAZOL 3 OL; DEUTERIUM; FLUORINE 18; NITROIMIDAZOLE DERIVATIVE; TRITIUM;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOTOPE LABELING; OXIDATION; POSITRON EMISSION TOMOGRAPHY; STEREOSPECIFICITY;

MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROIMIDAZOLES; NUCLEOSIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRITIUM;

EID: 44149085659     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.04.055     Document Type: Article

References (30)

1. Weissleder R., and Mahmood U. Radiology 219 (2001) 316
2. Bunn H.F., and Poyton R.O. Physiol. Rev. 76 (1996) 839
3. Dachs G.U., and Stratford I.J. Br. J. Cancer 74 (1996) S126
4. Gray L.H., Conger A.D., Ebert M., Hornsey S., and Scott O.C. Br. J. Radiol. 26 (1953) 638
5. Urtasun R.C., Parliament M.B., McEwan A.J., Mercer J.R., Mannan R.H., Wiebe L.I., Morin C., and Chapman J.D. Br. J. Cancer 74 (1996) S209
6. Al-Arafaj A., Ryan E.A., Hutchinson K., Mannan R.H., Mercer J., Wiebe L.I., and McEwan A.J.B. Eur. J. Nucl. Med. 21 (1994) 1338
7. Parliament M.B., Chapman J.D., Urtasun R.C., McEwan A.J., Golberg L., Mercer J.R., Mannan R.H., and Wiebe L.I. Br. J. Radiol. 65 (1991) 90
8. Groshar D., McEwan A.J.B., Parliament M.B., Urtasun R.C., Golberg L.E., Hoskinson M., Mercer J.R., Mannan R.H., Wiebe L.I., and Chapman J.D. J. Nucl. Med. 34 (1993) 885
9. McEwan A.J.B., Skeith K.J., Mannan R.H., Davies N., Jamali F., Schmidt R., Golberg K., and Wiebe L.I. J. Nucl. Med. 38 (1997) 300
10. Vinjamuri S., O'Driscol K., Maltby P., McEwan A.J., Wiebe L.I., and Critchley M. Clin. Nucl. Med. 24 (1999) 891
11. Biaglow J.E., Varnes M.E., Roizen-Towle L., Clark E.P., Epp E.R., Astor M.B., and Hall E.J. Biochem. Pharmacol. 35 (1986) 77
12. Kumar P., Stypinski D., Xia H., McEwan A.J.B., Machulla H.-J., and Wiebe L.I. J. Labelled Compd. Radiopharm. 42 (1999) 3
13. Reischl G., Ehrlichmann W., Bieg C., Kumar P., Wiebe L.I., and Machulla H.-J. Appl. Radiat. Isot. 62 (2005) 897
14. Sorger D., Patt M., Kumar P., Wiebe L.I., Barthel H., Seese A., Dannenberg C., Tannapfel A., and Osama Sabri R.K. Nucl. Med. Biol. 30 (2003) 317
15. Hicks et al. Unpublished results.
16. McEwan et al. Unpublished results.
17. Beck, R.; Picchio, M.; Seidl, S.; Haubner, R.; Machulla, H.-J.; Kumar, P.; Wiebe, L. I.; Schwaiger, M.; Piert, M. Abstract of Papers, 52nd Annual Meeting of Society of Nuclear Medicine, Toronto, Canada, June 18-22, 2005.
18. 3s and CHs), 61.28 (C-5′), 71.07 (C-2′), 72.06 (C-4′), 82.20 (C-3′), 90.38 (C-1′), 122.31 (C-4), 127.94 (C-5), 152.9 (C-2), respectively.
19. 2 calcd 510.20623; found 510.20664 (100%).
20. 2 (1 mL) was cooled to 0 °C. Once the temperature was maintained, acetic anhydride (15 μL; 0.15 mmol) in pyridine (25 μL) was added to this solution. Depending on the reaction method, 2 or 4 (24 mg, 0.05 mmol) was added to this solution after 3 min and the reaction was stirred for the required period (3 h in case of 2 and 2 h when 4 was used as a precursor). Once the TLC examination (system B) showed complete disappearance of the starting material, the solvents were removed by vacuum-assisted evaporation. This intermediate product 5 was not isolated and used as such in deuteration reaction.
21. 2D calcd 511.21251; found 511.21240 (100%).
22. Angyal S.J., and Evans M.B. Aust. J. Chem. 25 (2004) 1513
23. Silverstein, R. M.; Bassler, G. C.; Morril, T. C. In Spectrometric Identification of Organic Compounds, 4th ed.; John Wiley & Sons, USA, 1981, p 257.
24. 6NaD calcd 269.06028; found 269.06016 (100%).
25. 4D calcd 200.07761; found 200.07765 (100%).
26. Prestegard J.H., Miner V.W., and Tyrell P.M. Proc. Natl. Acad. Sci. U.S.A. 80 (1983) 7192
27. Crawford A., Hunter B.K., and Wood J.M. Appl. Environ. Microbiol. 53 (1987) 2445
28. Dziembowska T., and Rozwadowski Z. Curr. Org. Chem. 5 (2001) 289
29. Foldesi A., Kundu M., Dinya Z., and Chattopadhyaya J. Helv. Chim. Acta 87 (2004) 742
30. Foldesi A., Trifonova A., Dinya Z., and Chattopadhyaya J. J. Org. Chem. 66 (2001) 6560