Asymmetric synthesis of 2'-phosphonomethyl(3',4'-dihydroxybutyl)cytosine and -guanine nucleotides

Tetrahedron Asymmetry

Volumn 8, Issue 14, 1997, Pages 2299-2302

  Evans, Colleen A ^a   Hewgill, Randolph T ^a   Mansour, Tarek S ^a  

^a Shire Canada   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOTIDE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; ISOMER; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030824835     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00258-9     Document Type: Article

References (12)

1. Field, A. K.; Davies, M. E.; De Witt, C.; Perry, H. C.; Liou, R.; Germershausen, J.; Karkas, J. D.; Ashton, W. T.; Johnston, D. B. R.; Tolman, R. L. Proc. Natl. Acad. Sci. USA. 1983, 90, 4139-4143.
2. For a review see Mansour, T. S.; Storer, R. Curr. Pharm, Design 1997, 3, 227-264.
3. The synthesis of phosphonylmethoxyalkyl derivatives of adenine has been reported. Rosenberg, I.; Holy, A.; Masojidkova, M. Collect. Czech. Chem. Commun. 1988, 53, 2753-2777.
4. Naesens, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Neyts, J.; De Clercq, E. Antivir. Chem. Chemother. 1997, 8, 1-23.
5. Abushanab, E. In Nucleosides and Nucleotides an Antitumor and Antiviral Agents; Chu, C. K. and Baker, D. C.; Plennum Press; New York, 1993; pp. 159-175.
6. Saibaba, R.; Sarma, M. S. P.; Abushanab, E. Syn. Commun. 1989, 19, 3077-3086.
7. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineuni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602.
8. Belleau, B. R.; Evans, C. A.; Tse, H. L. A.; Jin, H.; Dixit, D. M.; Mansour, T. S. Tetrahedron Lett. 1992, 33, 6949-6952.
9. Evans, C. A.; Dixit, D. M.; Siddiqui, M. A.; Jin, H.; Tse, H. L. A.; Cimpoia, A.; Bednarski, K.; Breining, T.; Mansour, T. S. Tetrahedron: Asymmetry 1993, 4, 2319-2322.
10. A similar strategy was reported for the synthesis of 2′-substituted PMEG analogues. Yu, K.-L.; Bronson, J. J.; Yang, Y.; Patick, A.; Alam, M.; Brankovan, V.; Datema, R.; Hitchcock, M. J. M.; Martin, J. C. J. Med. Chem. 1993, 36, 2726-2738.
11. For a precedent on Mitsunobu coupling in acyclonucleotide synthesis see Harnden,M. R.; Jennings, L. J.; Parking, A. Synthesis 1991, 947-950.
12. 13C NMR, uv) and combustion data (C,H,N) were obtained.