A-Ring Modified Taxanes : 13-Aza Derivatives

Medicinal Chemistry Research

Volumn 6, Issue 4, 1996, Pages 264-292

  Menichincheri, Maria ^a   Ceccarelli, Walter ^a   Fusar Bassini, Domenico ^a   Vanotti, Ermes ^a   Ciomei, Marina ^a   Mongelli, Nicola ^a   Pinciroli, Vittorio ^a   Vulpetti, Anna ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

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EID: 0008269938     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (55)

1. (a) Schiff, P.B.; Fant, J.; Horwitz, S.B. Nature 1979, 277, 665-667; (b) Grover, S.; Rimoldi, J.R.; Molinero, A.A.; Chaudhary, A.G.; Kingston, D.G.I.; Hamel, E. Biochemistry 1995, 34, 3927-3934.
2. (a) Schiff, P.B.; Fant, J.; Horwitz, S.B. Nature 1979, 277, 665-667; (b) Grover, S.; Rimoldi, J.R.; Molinero, A.A.; Chaudhary, A.G.; Kingston, D.G.I.; Hamel, E. Biochemistry 1995, 34, 3927-3934.
3. McGuire, W.P.; Rowinsky, E.K.; Rosenchein, N.B.; Grumbine, F.C.; Ettinger, D.S.; Armstrong, D.K.; Donehower, R.C. Ann.Intern.Med. 1989, 111, 273-279.
4. Rowinsky, E.K.; Cazenave, L.A.; Donehower, R.C. J. Natl.Cancer Inst. 1990, 82, 1247-1259.
5. Georg, G.I.; Chen, T.T.; Ojima, I.; Vyas, D.M., Eds. Taxane Anticancer Agents: Basic Science and Current Status; ACS Symposium Series 583, American Chemical Society: Washington, DC, 1995.
6. (a) For reviews on SAR of paclitaxel, see Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Current Pharmaceutical Design 1995, 1, 95-112; (b) Hepperle, M.; Georg, G.I. Drugs of the Future 1994, 19, 573.
7. (a) For reviews on SAR of paclitaxel, see Guénard, D.; Guéritte-Voegelein, F.; Lavelle, F. Current Pharmaceutical Design 1995, 1, 95-112; (b) Hepperle, M.; Georg, G.I. Drugs of the Future 1994, 19, 573.
8. (a) Bollag, D.M.; McQueney, P.A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C.M. Cancer Research 1995, 55, 2325-2333; (b) Ter Haar, E.; Kowalski, R.J.; Hamel, E.; Lin, C.M.; Longley, R.E.; Gunasekera, S.P.; Rosenkranz, H.S.; Day, B.W. Biochemistry 1996, 35, 243-250.
9. (a) Bollag, D.M.; McQueney, P.A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C.M. Cancer Research 1995, 55, 2325-2333; (b) Ter Haar, E.; Kowalski, R.J.; Hamel, E.; Lin, C.M.; Longley, R.E.; Gunasekera, S.P.; Rosenkranz, H.S.; Day, B.W. Biochemistry 1996, 35, 243-250.
10. Menichincheri, M.; Botta, M.; Ceccarelli, W.; Ciomei, M.; Corelli, F.; D'Anello, M.; Fusar-Bassini, D.; Mongelli, N.; Pesenti, E.; Pinciroli, V.; Tafi, A.; Vanotti, E. Medicinal Chemistry Research 1995, 5, 534-555.
11. Suffness, M. Annual Reports in Medicinal Chemistry 1993, 305-314.
12. While reviewing the manuscript a publication by Chen and coworkers, relative to the synthesis of C-13 amidopaclitaxel analogs has been issued : Chen, S.-H.; Farina, V.; Vyas, D.M.; Doyle, T.W.; Long, B.H.; Fairchild, C. J.Org.Chem. 1996, 61, 2065-2070.
13. Hoemann, M.Z.; Vander Velde, D.G.; Aubè, J.; Georg, G.I.; Jayasinghe, L.R. J. Org.Chem. 1995, 60, 2918-2921.
14. Jayasinghe, L.R.; Datta, A.; Ali, S.M.; Zygmunt, J.; Vander Velde, D.G.; Georg, G.I. J.Med.Chem. 1994, 37, 2981-2984.
15. Marder, R.; Dubois, J.; Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Tetrahedron 1995, 51, 1985-1994.
16. Harriman, G.C.B.; Jalluri, R.K.; Grunewald, G.L.; Vander Velde, D.G.; Georg, G.I. Tetrahedron Lett. 1995, 36, 8909-8912.
17. Kelly, R.C.; Wicnienski, N.A.; Gebhard, I.; Quails, S.J.; Han, F.; Dobrowolski, P.J.; Nidy, E.G.; Johnson, R.A. J.Am.Chem.Soc. 1996, 118, 919-920.
18. Chordia, M.D.; Gharpure, M.M.; Kingston, D.G.I. Tetrahedron 1995, 51, 12963-12970.
19. (a) Senilh, V.; Guéritte, F.; Guénard, D.; Colin, M.; Potier, P. C.R. Acad.Sc.Paris 1984, 299, 1039-1043; (b) Nicolaou, K.C.; Ueno, H.; Liu, J-J.; Nantermet, P.G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J.Am.Chem.Soc. 1995, 117, 653-659.
20. (a) Senilh, V.; Guéritte, F.; Guénard, D.; Colin, M.; Potier, P. C.R. Acad.Sc.Paris 1984, 299, 1039-1043; (b) Nicolaou, K.C.; Ueno, H.; Liu, J-J.; Nantermet, P.G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J.Am.Chem.Soc. 1995, 117, 653-659.
21. 3-4), 198.3,200.2 (9+13).
22. Bastart, J-P.; Leconte, J-P. WO9526967 (1995).
23. 9
24. Rouillard, M.; Girault, Y.; Azzaro, M. Org. Magn. Reson. 1983, 21 (6), 357-360.
25. Hawkes, G.E.; Herwing, K.; Roberts, J.D. J.Org.Chem. 1974, 39 (8), 1017-1028.
26. 3 the oxime OH group is not detectable or presents a broad signal.
27. NOESY cross-peaks of taxols in DMSO-d6 at 400 and 600 MHz are almost negligible.
28. (a) Greene, A.E.; Denis, J.-N.; Guénard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J.Am.Chem.Soc. 1988, 110, 5917-5919; (b) Denis, J.-N.; Greene, A.E.; Guénard, D.; Guéritte-Voegelein, F. EP 336840, 1989; (c) Commerçon, A.; Bezard, D.; Bernard, F.; Bouzard, J.D. Tetrahedron Lett. 1992, 33, 5185-5188.
29. (a) Greene, A.E.; Denis, J.-N.; Guénard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J.Am.Chem.Soc. 1988, 110, 5917-5919; (b) Denis, J.-N.; Greene, A.E.; Guénard, D.; Guéritte-Voegelein, F. EP 336840, 1989; (c) Commerçon, A.; Bezard, D.; Bernard, F.; Bouzard, J.D. Tetrahedron Lett. 1992, 33, 5185-5188.
30. (a) Greene, A.E.; Denis, J.-N.; Guénard, D.; Guéritte-Voegelein, F.; Mangatal, L.; Potier, P. J.Am.Chem.Soc. 1988, 110, 5917-5919; (b) Denis, J.-N.; Greene, A.E.; Guénard, D.; Guéritte-Voegelein, F. EP 336840, 1989; (c) Commerçon, A.; Bezard, D.; Bernard, F.; Bouzard, J.D. Tetrahedron Lett. 1992, 33, 5185-5188.
31. At present, we have no explanations for this racemization and for the differential reactivity of the two oximes.
32. Hydrazine has been previously used to remove 10-acetyl : (a) Johnson, R.A.; Nidy, E.G.; Dobrowolski, P.J.; Gebhard, I.; Quails, S.J.; Wicnienski, N.A.; Kelly, R.C. Tetrahedron Lett. 1994, 35, 7893-7896; (b) Datta, A.; Hepperle, M.; Georg, G.I. J.Org.Chem. 1995, 60, 761-763.
33. Hydrazine has been previously used to remove 10-acetyl : (a) Johnson, R.A.; Nidy, E.G.; Dobrowolski, P.J.; Gebhard, I.; Quails, S.J.; Wicnienski, N.A.; Kelly, R.C. Tetrahedron Lett. 1994, 35, 7893-7896; (b) Datta, A.; Hepperle, M.; Georg, G.I. J.Org.Chem. 1995, 60, 761-763.
34. Removal of 10-acetoxy on taxanes had been previously obtained with other methods : (a) Holton, R.A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668; (b) Chen, S.-H.; Fairchild, C.; Mamber, S.W.; Farina, V. J.Org.Chem. 1993, 58, 2927-2928; (c) Chaudhary, A.G.; Kingston, D.G.I. Tetrahedron Lett. 1993, 34, 4921-4924; (d) Georg, G.I.; Cheruvallath, Z.S. J.Org.Chem. 1994, 59, 4015-4018.
35. Removal of 10-acetoxy on taxanes had been previously obtained with other methods : (a) Holton, R.A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668; (b) Chen, S.-H.; Fairchild, C.; Mamber, S.W.; Farina, V. J.Org.Chem. 1993, 58, 2927-2928; (c) Chaudhary, A.G.; Kingston, D.G.I. Tetrahedron Lett. 1993, 34, 4921-4924; (d) Georg, G.I.; Cheruvallath, Z.S. J.Org.Chem. 1994, 59, 4015-4018.
36. Removal of 10-acetoxy on taxanes had been previously obtained with other methods : (a) Holton, R.A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668; (b) Chen, S.-H.; Fairchild, C.; Mamber, S.W.; Farina, V. J.Org.Chem. 1993, 58, 2927-2928; (c) Chaudhary, A.G.; Kingston, D.G.I. Tetrahedron Lett. 1993, 34, 4921-4924; (d) Georg, G.I.; Cheruvallath, Z.S. J.Org.Chem. 1994, 59, 4015-4018.
37. Removal of 10-acetoxy on taxanes had been previously obtained with other methods : (a) Holton, R.A.; Somoza, C.; Chai, K.-B. Tetrahedron Lett. 1994, 35, 1665-1668; (b) Chen, S.-H.; Fairchild, C.; Mamber, S.W.; Farina, V. J.Org.Chem. 1993, 58, 2927-2928; (c) Chaudhary, A.G.; Kingston, D.G.I. Tetrahedron Lett. 1993, 34, 4921-4924; (d) Georg, G.I.; Cheruvallath, Z.S. J.Org.Chem. 1994, 59, 4015-4018.
38. Py, S.; Khuong-Huu, F. Tetrahedron Lett. 1995, 36, 1661-1664.
39. The poor reactivity of the C-9 ketone is attributable to its scarce accessibility (Datta, A.; Vander Velde, D.G.; Georg, G.I. Tetrahedron Lett. 1995,36, 1985-1988). So, the lack of the C-10 acetoxy should facilitate its reduction that occurs, in fact, with samarium diiodide on 10-deacetoxylated analogs : ref. 28 and Georg, G.I.; Cheruvallath, Z.S.; Vander Velde, D.G. Tetrahedron Lett. 1995, 36, 1783-1786. We subjected 7-TES-10-deacetoxy-13-oxo baccatin to reduction with sodium cyanoborohydride recovering only starting material. For reduction with sodium borohydride see ref. 31.
40. The poor reactivity of the C-9 ketone is attributable to its scarce accessibility (Datta, A.; Vander Velde, D.G.; Georg, G.I. Tetrahedron Lett. 1995,36, 1985-1988). So, the lack of the C-10 acetoxy should facilitate its reduction that occurs, in fact, with samarium diiodide on 10-deacetoxylated analogs : ref. 28 and Georg, G.I.; Cheruvallath, Z.S.; Vander Velde, D.G. Tetrahedron Lett. 1995, 36, 1783-1786. We subjected 7-TES-10-deacetoxy-13-oxo baccatin to reduction with sodium cyanoborohydride recovering only starting material. For reduction with sodium borohydride see ref. 31.
41. (a) Verardo, G.; Giumanini, A.G.; Strazzolini, P.; Poiana, M. Synth.Comm. 1988, 18, 1501-1511; (b) Guziec, F.S.Jr.; Russo, J.M. Synthesis 1984, 479-481.
42. (a) Verardo, G.; Giumanini, A.G.; Strazzolini, P.; Poiana, M. Synth.Comm. 1988, 18, 1501-1511; (b) Guziec, F.S.Jr.; Russo, J.M. Synthesis 1984, 479-481.
43. 4/CuBr was reported for 7-TES-10-deacetyl baccatin : Appendino, G.; Jakupovic, J.; Cravotto, G.; Enriù, R.; Varese, M.; Bombardelli, E. Tetrahedron Lett. 1995, 36, 3233-3236.
44. Other derivatives prepared with this procedure were isopropyl, phenyl and benzyl enamides.
45. (a) Mangatal, L.; Adeline, M.-T.; Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Tetrahedron 1989, 45, 4177-4190; (b) Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Acc.Chem.Res. 1993, 26, 160-167.
46. (a) Mangatal, L.; Adeline, M.-T.; Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Tetrahedron 1989, 45, 4177-4190; (b) Guénard, D.; Guéritte-Voegelein, F.; Potier, P. Acc.Chem.Res. 1993, 26, 160-167.
47. Guéritte-Voegelein, F.; Guénard, D.; Lavelle, F.; Le Goff, M.-T.; Mangatal, L.; Potier, P. J.Med.Chem. 1991, 34, 992-998.
48. Commerçon, A.; Bezard, D.; Bernard, F.; Bouzard, J.D. Tetrahedron Lett. 1992, 33, 5185-5188.
49. Swindell, C.S.; Krauss, N.E.; Horwitz, S.B.; Ringel, I. J.Med.Chem. 1991, 34, 1176-1184.
50. 7
51. BIOSYM Technologies Inc., San Diego, CA.
52. Dubois, J.; Guénard, D.; Guéritte-Voegelein, F.; Guedira, N.; Potier, P.; Gillet, B.; Beloeil, J.-C. Tetrahedron 1993, 49, 6533-6544.
53. Kontoyianni, M.; Bowen, J.P. J. Computational Chem. 1992, 13, 657-666.
54. Miller, R.W.; Powell, R.G.; Smith, C.R.Jr. J.Org.Chem. 1981, 46, 1469-1474.
55. Patwardan, S.A.; Sukh Dev. Synthesis 1974, 348-349.