Propargyl-substituted phosphonocarboxylates: Efficient synthesis and application to click chemistry

Synthesis

Volumn , Issue 21, 2009, Pages 3579-3588

  Artyushin, Oleg I ^a   Osipov, Sergey N ^a   Röschenthaler, Gerd Volker ^b   Odinets, Irina L ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b UNIVERSITY OF BREMEN   (Germany)

Author keywords

1,3 Dipolar cycloaddition; Alkylation; Azides; Ethylidenephosphonate; Phosphonocarboxylates; Phosphorylated 1,2,3 triazoles; Sodium acetylenide

Indexed keywords

1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY; DIPOLAR CYCLOADDITIONS; DIRECT ALKYLATION; EFFICIENT SYNTHESIS; GRAM SCALE; ORGANIC AZIDES; PROPARGYL; PROPARGYL BROMIDES; TRIFLUOROMETHYL;

ALKYLATION; CYCLOADDITION; HYDROCARBONS; NITROGEN COMPOUNDS; PHOSPHORYLATION; SODIUM;

SYNTHESIS (CHEMICAL);

AMIDE; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER; ETHYL 2 (DIETHOXYPHOSPHORYL) 1 [[(2,2 DIMETHYL 1 OXOPROPOXY)METHYL] 1H 1,2,3 TRIAZOL 4 YL] 2 FLUOROPROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 2 (2 PROPYNYL)PENT 4 YNOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 2 FLUORO 3 [1 (4 FLUOROBENZYL) 1H 1,2,3 TRIAZOL 4 YL]PROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 2 FLUOROPENT 4 YNOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 2 METHYLPENT 4 YNOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 3 [1 (2,3,4,6 TETRA O ACETYL B DEXTROGLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL] 2 METHYLPROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 3 [1 (2,3,4,6 TETRA O ACETYL B GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL] 2 FLUOROPROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 3 [1 (2,3,4,6 TETRA O ACETYL B GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL]PROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 3 [1 [3 (DIETHOXYPHOSPHORYL)PROPYL] 1H 1,2,3 TRIAZOL 4 YL] 2 FLUOROPROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL) 3 [1 [3 (DIETHOXYPHOSPHORYL)PROPYL] 1H 1,2,3 TRIAZOL 4 YL] 2 METHYLPROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL)3 [1 [3 (DIETHOXYPHOSPHORYL)BUTYL] 1H 1,2,3 TRIAZOL 4 YL]PROPANOATE; ETHYL 2 (DIETHOXYPHOSPHORYL)PENT 4 YNOATE; ETHYL 3 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL) 2 (DIETHOXYPHOSPHORYL) 2 METHYLPROPANOATE; ETHYL 3 (1 BENZYL 1H 1,2,3 TRIAZOL 4 YL) 2 [(1 BENZYL 1H 1,2,3 TRIAZOL 4 YL)METHYL] 2 (DIETHOXYPHOSPHORYL)PROPANOATE; ETHYL 3 [1 (1 ADAMANTYL) 1H 1,2,3 TRIAZOL 4 YL] 2 (DIETHOXYPHOSPHORYL) 2 FLUOROPROPANOATE; ETHYL 3 [1 (1 ADAMANTYL) 1H 1,2,3 TRIAZOL 4 YL] 2 (DIETHOXYPHOSPHORYL)PROPANOATE; ETHYL 3 [1 (2 TERT BUTOXY 2 OXOETHYL) 1H 1,2,3 TRIAZOL 4 YL] 2 (DIETHOXYPHOSPHORYL) 2 METHYLPROPANOATE; ETHYL 3 [1 (2 TERT BUTOXY 2 OXOETHYL) 1H 1,2,3 TRIAZOL 4 YL] 2 [[1 (2 TERT BUTOXY 2 OXOETHYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 (DIETHOXYPHOSPHORYL)PROPANOATE; ETHYL 3 [1 [2 TERT BUTOXY 2 OXOETHYL) 1H 1,2,3 TRIAZOL 4 YL] 2 (DIETHOXYPHOSPHORYL) 2 FLUOROPROPANOATE; ETHYL 3 [1 [3 (HYDROXYMETHYL) 5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL)TETRAHYDROFURAN 2 YL] 1H 1,2,3 TRIAZOL 4 YL] 2 (DIETHOXYPHOSPHORYL) 2 FLUOROPROPANOATE; ETHYL 3 [1 [3 (HYDROXYMETHYL) 5 [5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL]TETRAHYDROFURAN 2 YL] 1H 1,2,3 TRIAZOL 4 YL) 2 (DIETHOXYPHOSPHORYL)PROPANOATE; ETHYLIDENEPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; SODIUM ACETYLENIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADDITION REACTION; ALKYLATION; ARTICLE; CATALYSIS; CYCLOADDITION; DRUG ACTIVITY; DRUG SYNTHESIS;

EID: 72049106672     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216982     Document Type: Article

References (43)

1. (a) Breuer, E. The development of bisphosphonates as drugs, In Analogue-based Drug Discovery; Fischer, J.; Ganellin, C. R., Eds.; Wiley-VCH: Berlin, 2006, 371-384.
2. (b) Catterall, J. B.; Cawston, T. E. Arthritis Research and Therapy 2002, 5, 12.
3. (c) Graham, R.; Russell, G. Pediatrics 2007, 119, S150.
4. (a) Fleisch, H. Bisphosphonates in Bone Disease, In From the Laboratory to the Patient; Parthenon: New York, 1995.
5. (b) Papapoulos, S. E.; Landman, J. O.; Bijvoet, O. L. M.; Loewik, C. W. G. M.; Valkema, R.; Pauwels, E. K. J.; Vermeij, P. Bone 1992, 13, S41.
6. (c) Yates, A. J.; Rodan, G. A. Drug Discovery Today 1998, 3, 69.
7. (d) Socrates, E.; Papapoulos, M. D. Am. J. Med. 1993, 95, 48S.
8. (e) Giannini, S.; D'Angelo, A. L.; Sartory, G. L.; Passeri, G.; Garbonare, L. D.; Crebaldi, C. Obst. Gynecol. 1996, 88, 431.
9. (f) Uludag, H. Curr. Pharm. Des. 2002, 8, 99.
10. (a) Szajnman, S. H.; Montalvetti, A.; Wang, Y.; Docampo, R.; Rodriguez, J. B. Bioorg. Med. Chem. Lett. 2003, 13, 3231.
11. (b) Garzoni, L. R.; Caldera, A.; Nazareth, L.; Meirelles, M.; Castro, S. L.; Docampo, R.; Meints, G. A.; Oldfield, E.; Urbina, J. A. Int. J. Antimicrob. Agents 2004, 23, 273.
12. (c) Garzoni, L. R.; Waghabi, M. C.; Baptista, M. M.; Castro, S. L.; Nazareth, L.; Meirelles, M.; Britta, C. C.; Docampo, R.; Oldfield, E.; Urbina, J. A. Int. J. Antimicrob. Agents 2004, 23, 286.
13. (d) Kotsikorou, E.; Song, Y.; Chan, J. M. W.; Faelens, S.; Tovian, Z.; Broderick, E.; Bakalara, N.; Docampo, R.; Oldfield, E. J. Med. Chem. 2005, 48, 6128.
14. (a) Sanders, J. M.; Song, Y.; Chan, J. M. W.; Zhang, Y.; Jennings, S.; Kosztowski, T.; Odeh, S.; Flessner, R.; Schwerdtfeger, C.; Kotsikorou, E.; Meints, G. A.; Gomez, A. O.; Gonzalez-Pacanowska, D.; Raker, A. M.; Wang, H.; van Beek, E. R.; Papapoulos, S. E.; Morita, C. T.; Oldfield, E. J. Med. Chem. 2005, 48, 2957.
15. (b) Coxon, F. P.; Ebetino, F. H.; Mules, E. H.; Seabra, M. C.; McKenna, C. E.; Rogers, M. J. Bone 2005, 37, 349.
16. (a) Rogers, M. J. Curr. Pharm. Des. 2003, 9, 2643.
17. (b) Sato, M.; Grasser, W.; Endo, N.; Akins, R.; Simmons, H.; Thompson, D. D.; Golub, E.; Rodan, G. A. J. Clin. Invest. 1991, 88, 2095.
18. (c) Masarachia, P.; Weinreb, M.; Balena, R.; Rodan, G. A. Bone 1996, 19, 281.
19. (d) Dunford, J. E.; Thompson, K.; Coxon, F. P.; Luckman, S. P.; Hahn, F. M.; Poulter, C. D.; Ebetino, F. H.; Rogers, M. J. J. Pharmacol. Exp. Ther. 2001, 296, 235.
20. (a) van Beek, E. R.; Lowik, C.; van der Pluijm, G.; Papalous, S. E. J. Bone Miner. Res. 1999, 14, 722.
21. (b) Coxon, F. P.; Helfrich, M. H.; Van't, H. o. f. R.; Sebti, S.; Ralston, S. H.; Hamilton, A. D.; Rogers, M. J. J. Bone Miner. Res. 2000, 15, 1467.
22. (c) Graham, R.; Russell, G. Pediatrics 2007, 119, S150.
23. Engel, R. Handbook of Organophosphorus Chemistry; Marcel Dekker: New York, 1992, Chap. 11.
24. (a) Grem, J. L.; King, S. A.; O'Dwyer, P. J.; Leyland-Jones, B. Cancer Res. 1988, 48, 4441.
25. (b) Allewell, N. M.; Shi, D.; Morizono, H.; Tuchman, M. Acc. Chem. Res. 1999, 32, 885.
26. (c) Fetler, L.; Taue, P.; Hervé, G.; Cunin, R.; Brochón, J.-C. Biochemistry 2001, 40, 8773.
27. (d) Christopherson, R. I.; Lyons, S. D.; Wilson, P. K. Acc. Chem. Res. 2002, 35, 961.
28. Skarpos, H.; Osipov, S. N.; Vorob'eva, D. V.; Odinets, I. L.; Lork, E.; Röschenthaler, G.-V. J. Org. Biomol. Chem. 2007, 5, 2361.
29. (a) Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952.
30. (b) Tron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278; and references cited therein.
31. Artyushin, O. I.; Vorob'eva, D. V.; Vasil'eva, T. P.; Osipov, S. N.; Roeschenthaler, G.-V.; Odinets, I. L. Heteroat. Chem. 2008, 19, 293.
32. Chang, K.-H.; Lee, L.; Chen, J.; Li, W.-S. Chem. Commun. 2006, 629.
33. Kirschleger, B.; Quengnec, R. Synthesis 1986, 926.
34. Chambers, J. R.; Isbell, A. F. J. Org. Chem. 1964, 29, 832.
35. Ravikumar, V. T.; Swaminathan, S.; Rajagopalan, K. Tetrahedron Lett. 1984, 6045.
36. Blaszczyk, E.; Krawczyk, H.; Janecki, T. Synlett 2004, 2685.
37. Pudovik, A. N.; Khusainova, N. G. Zh. Obshch. Khim. 1969, 39, 2426.
38. (a) Lee, L. V.; Mitchell, L.; Huang, S.-J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 2003, 125, 9588.
39. (b) Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; van der Eycken, E. Org. Lett. 2004, 6, 4223.
40. (c) Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897.
41. Machleidt, H.; Wessendort, R. Justus Liebigs Ann. Chem. 1964, 674, 1.
42. (a) Dolby, L. J.; Riddle, G. N. J. Org. Chem. 1967, 32, 3481.
43. (b) Gallagher, G. Jr.; Webb, R. L. Synthesis 1974, 122.