SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 17, Issue 5, 2011, Pages 1649-1659

Diastereoselective synthesis of cyclosaligenyl-nucleosyl-phosphotriesters

(3) Riosa Morales, Edwuin H a Balzarini, Jan b Meier, Chris a

a UNIVERSITY OF HAMBURG (Germany)

b REGA INSTITUTE FOR MEDICAL RESEARCH (Belgium)

Author keywords

antiviral agents; chiral phosphates; cyclosaligenyl; nucleotides; stereoselective synthesis

Indexed keywords

ANTIVIRAL ACTIVITIES; ANTIVIRAL AGENTS; AROMATIC RESIDUES; CHIRAL AUXILIARIES; CHIRAL CHEMICALS; CHIRAL GROUPS; CHIRAL PHOSPHATES; CYCLOSALIGENYL; DIASTEREOMERIC; DIASTEREOMERIC EXCESS; DIASTEREOMERS; DIASTEREOSELECTIVE; DIASTEREOSELECTIVE SYNTHESIS; PRONUCLEOTIDES; STEREOSELECTIVE SYNTHESIS; SUBSTITUTION PATTERNS; SYNTHESIS ROUTE; THIAZOLINE; TROJAN HORSE;

NUCLEOTIDES; PHOSPHATES;

STEREOSELECTIVITY;

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CYCLOSALIGENYL 3' AZIDO 2',3' DIDEOXYTHYMIDINE MONOPHOSPHATE; CYCLOSALIGENYL 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE MONOPHOSPHATE; DIDEOXYNUCLEOTIDE; DRUG DERIVATIVE; NUCLEOTIDE; ORGANOPHOSPHATE; STAVUDINE; ZIDOVUDINE;

ARTICLE; CHEMISTRY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-HIV AGENTS; DIDEOXYNUCLEOTIDES; HUMANS; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDES; PHOSPHORIC ACID ESTERS; STAVUDINE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; ZIDOVUDINE;

EID: 79251628040 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201002657 Document Type: Article

Times cited : (14)

References (50)

1
- 0022346409
- J. W. Curran, W. M. Morgan, A. M. Hardy, H. W. Jaffe, W. W. Darrow, D. R. Dowdle, Science 1985, 229, 1352-1357.
- (1985) Science , vol.229 , pp. 1352-1357
- Curran, J.W.¹ Morgan, W.M.² Hardy, A.M.³ Jaffe, H.W.⁴ Darrow, W.W.⁵ Dowdle, D.R.⁶

2
- 0020596551
- Isolation of a T-lymphotropic Retrovirus from a Patient at Risk for Acquired Immune Deficiency Syndrome (AIDS)
- F. Barre-Sinoussi, J. C. Cherman, F. Rey, M. T. Nugeyre, S. Chamaret, T. Gruest, C. Dauguet, C. Axler-Blin, F. Vezin-Brun, C. Routioux, W. Rosenbaum, L. Montagnier, Isolation of a T-lymphotropic Retrovirus from a Patient at Risk for Acquired Immune Deficiency Syndrome (AIDS), Science 1983, 220, 868-871.
- (1983) Science , vol.220 , pp. 868-871
- Barre-Sinoussi, F.¹ Cherman, J.C.² Rey, F.³ Nugeyre, M.T.⁴ Chamaret, S.⁵ Gruest, T.⁶ Dauguet, C.⁷ Axler-Blin, C.⁸ Vezin-Brun, F.⁹ Routioux, C.¹⁰ Rosenbaum, W.¹¹ Montagnier, L.¹²

3
- 0029011730
- E. Dea Clercq, J. Med. Chem. 1995, 38, 2491.
- (1995) J. Med. Chem. , vol.38 , pp. 2491
- Dea Clercq, E.¹

4
- 0028205185
- J. Balzarini, Pharm. World Sci. 1994, 16, 113-126
- (1994) Pharm. World Sci. , vol.16 , pp. 113-126
- Balzarini, J.¹

5
- 79251601742
- E. Dea Clercq, Nat. Rev. Drug Discovery 2002, 1, 13-25.
- (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 13-25
- Dea Clercq, E.¹

6
- 0001720586
- in (Ed.: E. Dea Clercq), JAI Press Inc., Greenwich (Connecticut), London (England), pp.a .
- P. Herdewijn, J. Balzarini, E. De Clercq, in Advances in Antiviral Drug Design, Vol.a 1 (Ed.:, E. Dea Clercq,), JAI Press Inc., Greenwich (Connecticut), London (England), 1993, pp.a 233-318.
- (1993) Advances in Antiviral Drug Design , vol.1 , pp. 233-318
- Herdewijn, P.¹ Balzarini, J.² Clercq, E.D.³

7
- 0022996630
- P. A. Furman, J. A. Fyfe, M. H. St. a Clair, K. J. Weinhold, J. L. Rideout, G. A. Freeman, S. N. Lehrmann, D. Bolognesi, S. Broder, Proc. Natl. Acad. Sci. USA 1986, 83, 8333-8337.
- (1986) Proc. Natl. Acad. Sci. USA , vol.83 , pp. 8333-8337
- Furman, P.A.¹ Fyfe, J.A.² Clair, M.H.³ Weinhold, K.J.⁴ Rideout, J.L.⁵ Freeman, G.A.⁶ Lehrmann, S.N.⁷ Bolognesi, D.⁸ Broder, S.⁹

8
- 0029086438
- S. A. Riddler, R. E. Anderson, J. W. Mellors, Antiviral Res. 1995, 27, 189-203.
- (1995) Antiviral Res. , vol.27 , pp. 189-203
- Riddler, S.A.¹ Anderson, R.E.² Mellors, J.W.³

9
- 0026046476
- M. J. M. Hitchcock, Antiviral Chem. Chemother. 1991, 2, 125-132
- (1991) Antiviral Chem. Chemother. , vol.2 , pp. 125-132
- Hitchcock, M.J.M.¹

10
- 0028939311
- J. P. Sommadossi, J. Infect. Dis. (Suppl. 2) 1995, 171, 88-92.
- (1995) J. Infect. Dis. (Suppl. 2) , vol.171 , pp. 88-92
- Sommadossi, J.P.¹

11
- 0024592935
- J. Balzarini, P. Herdewijn, E. Dea Clercq, J. Biol. Chem. 1989, 264, 6127-6133.
- (1989) J. Biol. Chem. , vol.264 , pp. 6127-6133
- Balzarini, J.¹ Herdewijn, P.² Dea Clercq, E.³

12
- 79251636609
- Whole issue: "Pro-Nucleotide Development and Delivery of Biologically Active Nucleotide analogues"
- Whole issue: "Pro-Nucleotide Development and Delivery of Biologically Active Nucleotide analogues", Mini-Rev. Med. Chem. 2004, 4, 341-459.
- (2004) Mini-Rev. Med. Chem. , vol.4 , pp. 341-459

13
- 3042568734
- S. Peyrottes, D. Egron, I. Lefebvre, G. Gosselin, J.-L. Imbach, C. Perigaud, Mini-Rev. Med. Chem. 2004, 4, 395-408
- (2004) Mini-Rev. Med. Chem. , vol.4 , pp. 395-408
- Peyrottes, S.¹ Egron, D.² Lefebvre, I.³ Gosselin, G.⁴ Imbach, J.-L.⁵ Perigaud, C.⁶

14
- 0028843908
- J.-L. Girardet, C. Périgaud, A.-M. Aubertin, G. Gosselin, A. Kim, J.-L. Imbach, Bioorg. Med. Chem. Lett. 1995, 5, 2981-2984.
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2981-2984
- Girardet, J.-L.¹ Périgaud, C.² Aubertin, A.-M.³ Gosselin, G.⁴ Kim, A.⁵ Imbach, J.-L.⁶

15
- 19444368441
- K. R. Reddy, S. H. Boyer, M. D. Erion, Tetrahedron Lett. 2005, 46, 4321-4324
- (2005) Tetrahedron Lett. , vol.46 , pp. 4321-4324
- Reddy, K.R.¹ Boyer, S.H.² Erion, M.D.³

16
- 11144357250
- M. D. Erion, J. Am. Chem. Soc. 2004, 126, 5154-5163.
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 5154-5163
- Erion, M.D.¹

17
- 0030896486
- C. McGuigan, M.-J. Camarasa, H. Egberink, K. Hartmann, A. Karlsson, C. F. Perno, J. Balzarini, Int. Antiviral News 1997, 5, 19-21
- (1997) Int. Antiviral News , vol.5 , pp. 19-21
- McGuigan, C.¹ Camarasa, M.-J.² Egberink, H.³ Hartmann, K.⁴ Karlsson, A.⁵ Perno, C.F.⁶ Balzarini, J.⁷

18
- 0029975897
- C. McGuigan, D. Cahard, H. M. Sheeka, E. Dea Clercq, J. Balzarini, J. Med. Chem. 1996, 39, 1748-1753.
- (1996) J. Med. Chem. , vol.39 , pp. 1748-1753
- McGuigan, C.¹ Cahard, D.² Sheeka, H.M.³ Dea Clercq, E.⁴ Balzarini, J.⁵

19
- 33644778698
- C. Meier, Eur. J. Org. Chem. 2006, 1081-1102
- (2006) Eur. J. Org. Chem. , pp. 1081-1102
- Meier, C.¹

20
- 0003188936
- C. Meier, E. Dea Clercq, J. Balzarini, Eur. J. Org. Chem. 1998, 837-846
- (1998) Eur. J. Org. Chem. , pp. 837-846
- Meier, C.¹ Dea Clercq, E.² Balzarini, J.³

21
- 54549092707
- H. J. Jessen, J. Balzarini, C. Meier, J. Med. Chem. 2008, 51, 6592-6598
- (2008) J. Med. Chem. , vol.51 , pp. 6592-6598
- Jessen, H.J.¹ Balzarini, J.² Meier, C.³

22
- 58149097702
- N. Gisch, F. Pertenbreiter, J. Balzarini, C. Meier, J. Med. Chem. 2008, 51, 8115-8123
- (2008) J. Med. Chem. , vol.51 , pp. 8115-8123
- Gisch, N.¹ Pertenbreiter, F.² Balzarini, J.³ Meier, C.⁴

23
- 66749116603
- N. Gisch, J. Balzarini, C. Meier, J. Med. Chem. 2009, 52, 3464-3473
- (2009) J. Med. Chem. , vol.52 , pp. 3464-3473
- Gisch, N.¹ Balzarini, J.² Meier, C.³

24
- 33947693161
- C. Ducho, U. Görbig, S. Jessel, N. Gisch, J. Balzarini, C. Meier, J. Med. Chem. 2007, 50, 1335-1346
- (2007) J. Med. Chem. , vol.50 , pp. 1335-1346
- Ducho, C.¹ Görbig, U.² Jessel, S.³ Gisch, N.⁴ Balzarini, J.⁵ Meier, C.⁶

25
- 34147154785
- N. Gisch, J. Balzarini, C. Meier, J. Med. Chem. 2007, 50, 1658-1667.
- (2007) J. Med. Chem. , vol.50 , pp. 1658-1667
- Gisch, N.¹ Balzarini, J.² Meier, C.³

26
- 78149255637
- H. J. Jessen, T. Schulz, J. Balzarini, C. Meier, Angew. Chem. 2008, 120, 8847-8850
- (2008) Angew. Chem. , vol.120 , pp. 8847-8850
- Jessen, H.J.¹ Schulz, T.² Balzarini, J.³ Meier, C.⁴

27
- 55249108486
- Angew. Chem. Int. Ed. 2008, 47, 8719-8722.
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8719-8722

28
- 0032560234
- C. Meier, M. Lorey, E. Dea Clercq, J. Balzarini, J. Med. Chem. 1998, 41, 1417-1427.
- (1998) J. Med. Chem. , vol.41 , pp. 1417-1427
- Meier, C.¹ Lorey, M.² Dea Clercq, E.³ Balzarini, J.⁴

29
- 2442717713
- C. Meier, C. Ducho, U. Görbig, R. Esnouf, J. Balzarini, J. Med. Chem. 2004, 47, 2839-2852.
- (2004) J. Med. Chem. , vol.47 , pp. 2839-2852
- Meier, C.¹ Ducho, C.² Görbig, U.³ Esnouf, R.⁴ Balzarini, J.⁵

30
- 0033529048
- C. Meier, T. Knispel, E. Dea Clercq, J. Balzarini, J. Med. Chem. 1999, 42, 1604-1614
- (1999) J. Med. Chem. , vol.42 , pp. 1604-1614
- Meier, C.¹ Knispel, T.² Dea Clercq, E.³ Balzarini, J.⁴

31
- 0033529065
- C. Meier, T. Knispel, V. E. Marquez, M. A. Siddiqui, E. Dea Clercq, J. Balzarini, J. Med. Chem. 1999, 42, 1615-1624
- (1999) J. Med. Chem. , vol.42 , pp. 1615-1624
- Meier, C.¹ Knispel, T.² Marquez, V.E.³ Siddiqui, M.A.⁴ Dea Clercq, E.⁵ Balzarini, J.⁶

32
- 56249132165
- N. Gisch, J. Balzarini, C. Meier, J. Med. Chem. 2008, 51, 6752-6760.
- (2008) J. Med. Chem. , vol.51 , pp. 6752-6760
- Gisch, N.¹ Balzarini, J.² Meier, C.³

33
- 0001201788
- K. K. Ogilvie, D. J. Iwacha, Tetrahedron Lett. 1973, 14, 317-319
- (1973) Tetrahedron Lett. , vol.14 , pp. 317-319
- Ogilvie, K.K.¹ Iwacha, D.J.²

34
- 0015527834
- H. Weber, H. G. Khorana, J. Mol. Biol. 1972, 72, 219-249
- (1972) J. Mol. Biol. , vol.72 , pp. 219-249
- Weber, H.¹ Khorana, H.G.²

35
- 29644432244
- E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190-6191.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 6190-6191
- Corey, E.J.¹ Venkateswarlu, A.²

36
- 1342281506
- A. Meinzer, A. Breckel, B. A. Thaher, N. Manicone, H.-H. Otto, Helv. Chim. Acta 2004, 87, 90-105.
- (2004) Helv. Chim. Acta , vol.87 , pp. 90-105
- Meinzer, A.¹ Breckel, A.² Thaher, B.A.³ Manicone, N.⁴ Otto, H.-H.⁵

37
- 37049160530
- R. S. Cahn, C. K. Ingold, J. Chem. Soc. 1951, 612-622
- (1951) J. Chem. Soc. , pp. 612-622
- Cahn, R.S.¹ Ingold, C.K.²

38
- 0001720136
- R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413-447
- (1966) Angew. Chem. , vol.78 , pp. 413-447
- Cahn, R.S.¹ Ingold, C.K.² Prelog, V.³

39
- 84981828672
- Angew. Chem. Int. Ed. Engl. 1966, 5, 385-415.
- (1966) Angew. Chem. Int. Ed. Engl. , vol.5 , pp. 385-415

40
- 23044491533
- S. Jones, C. Smanmoo, Org. Lett. 2005, 7, 3271-3274
- (2005) Org. Lett. , vol.7 , pp. 3271-3274
- Jones, S.¹ Smanmoo, C.²

41
- 0038336475
- S. Jones, D. Selitsianos, Org. Lett. 2002, 4, 3671-3673.
- (2002) Org. Lett. , vol.4 , pp. 3671-3673
- Jones, S.¹ Selitsianos, D.²

42
- 79251631817
- S.-Y. Wu, J. E. Casida, Phosphorus Sulfur Silicon Relat. Elem. 1994, 88, 129-137
- (1994) Phosphorus Sulfur Silicon Relat. Elem. , vol.88 , pp. 129-137
- Wu, S.-Y.¹ Casida, J.E.²

43
- 0023552426
- Z. J. Lesnikowski, P. J. Wolkanin, W. Stec, Tetrahedron Lett. 1987, 28, 5535-5538
- (1987) Tetrahedron Lett. , vol.28 , pp. 5535-5538
- Lesnikowski, Z.J.¹ Wolkanin, P.J.² Stec, W.³

44
- 0001015246
- J. Michalski, M. Mikolajczyk, Tetrahedron 1966, 22, 3055-3059
- (1966) Tetrahedron , vol.22 , pp. 3055-3059
- Michalski, J.¹ Mikolajczyk, M.²

45
- 49949148673
- M. Mikolajczyk, Tetrahedron 1967, 23, 1543-1549
- (1967) Tetrahedron , vol.23 , pp. 1543-1549
- Mikolajczyk, M.¹

46
- 37049064758
- J. Michalski, M. Mikolajczyk, Chem. Commun. (London) 1965, 35-36.
- (1965) Chem. Commun. (London) , pp. 35-36
- Michalski, J.¹ Mikolajczyk, M.²

47
- 0003656383
- Harger and Row, London, Chaptera , pp.a .
- J. Emsley, D. Hall, The Chemistry of Phosphorus, Harger and Row, London, 1976, Chaptera 8, pp.a 306-349.
- (1976) The Chemistry of Phosphorus , pp. 306-349
- Emsley, J.¹ Hall, D.²

48
- 23044505158
- G. R. J. Thatcher, R. Kluger, Adv. Phys. Org. Chem. 1989, 25, 99-265.
- (1989) Adv. Phys. Org. Chem. , vol.25 , pp. 99-265
- Thatcher, G.R.J.¹ Kluger, R.²

49
- 0032731244
- J. Balzarini, L. Naesens, S. Aquaro, T. Knispel, C.-F. Perno, E. Dea Clercq, C. Meier, Mol. Pharmacol. 1999, 56, 1354-1361.
- (1999) Mol. Pharmacol. , vol.56 , pp. 1354-1361
- Balzarini, J.¹ Naesens, L.² Aquaro, S.³ Knispel, T.⁴ Perno, C.-F.⁵ Dea Clercq, E.⁶ Meier, C.⁷

50
- 78149262004
- C. Arbeloa Román, J. Balzarini, C. Meier, J. Med. Chem. 2010, 53, 7675-7681.
- (2010) J. Med. Chem. , vol.53 , pp. 7675-7681
- Arbeloa Román, C.¹ Balzarini, J.² Meier, C.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.