Tetrakis(trimethylsilyl) ethenylidene-1,1-bisphosphonate: A mild and convenient Michael acceptor for the synthesis of 2-aminoethylidene-1,1- bisphosphonic acids and their potassium salts

Synlett

Volumn , Issue 10, 2011, Pages 1370-1374

  Shevchuk, Michael V ^a   Sotiropoulos, Jean Marc ^b   Miqueu, Karinne ^b   Romanenko, Vadim D ^a   Kukhar, Valery P ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b UNIVERSITÉ DE PAU ET DES PAYS DE L'ADOUR   (France)

Author keywords

2 aminoethylidene 1,1 bisphosphonic acids; amines; ethenylidene 1,1 bisphosphonates; Michael addition; silicon

Indexed keywords

2 AMINOETHENYLIDENE 1,1 BISPHOSPHONIC ACID DERIVATIVE; AMINE; BISPHOSPHONIC ACID DERIVATIVE; POTASSIUM FLUORIDE; TETRAKIS(TRIMETHYLSILYL) ETHENYLIDENE 1,1 BISPHOSPHONIC ACID DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; MICHAEL ADDITION;

EID: 79958126852     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260566     Document Type: Article

References (46)

1. Zhang S, Gangal G, Uludag H, Chem. Soc. Rev. 2007 36 507
2. Russell R, Rogers M, Bone 1999 25 97
3. Breuer E, In Analogue-Based Drug Discovery Fischer J Ganellin R Wiley-VCH Weinheim 2006 371-384
4. Berlicki, Kafarski P, Curr. Org. Chem. 2005 9 1829
5. Reszka A A., Rodan A, Mini-Rev. Med. Chem. 2004 4 711
6. Drake M T., Clarke B L., Khosla S, Mayo Clin. Proc. 2008 83 1032
7. Rodan G A., Reszka A A., Curr. Mol. Med. 2002 2 571
8. Roelofs A J., Thompson K, Gordon S, Rogers M J., Clin. Cancer Res. 2006 12 6222s
9. Catterall J B., Cawston T E., Arthritis Res. Ther. 2002 5 12
10. Wilder L, Jaeggi K A., Green J R., Phosphorus, Sulfur Silicon Relat. Elem. 1999 144-146 5
11. Clézardin P, Ebetino F H., Fournier P G. J., Cancer Res. 2005 65 4971
12. Simoni D, Gebbia N, Invidiata F P., Eleopra M, Marchetti P, Rondanin R, Baruchello R, Provera S, Marchioro C, Tolomeo M, Marinelli L, Limongelli V, Novellino E, Kwaasi A, Dunford J, Buccheri S, Caccamo N, Dieli F, J. Med. Chem. 2008 51 6800
13. Wang L, Kamath A, Das H, Li L, Bukowski J, [nl] J. Clin. Invest. 2001 108 1349
14. Sanders J M., Ghost S, Chan J M. W., Meints G A., Wang H, Raker A M., Song Y, Colantino A, Burzynska A, Kafarski P, Morita C T., Oldfield E, J. Med. Chem. 2004 47 375
15. Szajnman S H., Liñares G E. G., Li Z.-H, Jiang C, Galizzi M, Bontempi E J., Ferella M, Moreno S N. J., Docampo R, Rodriguez J B., Bioorg. Med. Chem. 2008 16 3283
16. Martin M B., Grimley J S., Lewis J C., Heath H T. III., Bailey B N., Kendrick H, Yardley V, Caldera A, Lira R, Urbina J A., Moreno S N. J., Docampo R, Croft S L., Oldfield E, J. Med. Chem. 2001 44 909
17. Martin M B., Sanders J M., Kendrick H, de Luca-Fradley K, Lewis J C., Grimley J S., Van Brussel E M., Olsen J R., Meints G A., Burzynska A, Kafarski P, Croft S L., Oldfield E, J. Med. Chem. 2002 45 2904
18. Abdou W M., Shaddy A A., ARKIVOC 2009 (ix) 143
19. Wilder L, Jaeggi K A., Glatt M, Müller K, Bachmann R, Bisping M, Born A.-R, Cortesi R, Guiglia G, Jeker H, Klein R, Ramseier U, Schmid J, Schreiber G, Seltenmeyer Y, Green J R., J. Med. Chem. 2002 45 3721
20. Kukhar V P., Romanenko V D., In Amino Acids, Peptides and Proteins in Organic Chemistry Vol. 2 Hughes A B. Wiley-VCH Weinheim 2009 189-260
21. Zolotukhina M M., Krutikov V I., Lavrentev A N., Russ. Chem. Rev. (Engl. Transl.) 1993 62 647
22. Janecki T, Kdzia J, Wsek T, Synthesis 2009 1227
23. Enders D, Saint-Dizier A, Lannou M.-I, Lenzen A, Eur. J. Org. Chem. 2006 29
24. Vepsäläinen J J., Curr. Med. Chem. 2002 9 1201
25. For example, see:, Takeuchi M, Sakamoto S, Yoshida M, Abe T, Isomura Y, Chem. Pharm. Bull. 1993 41 688
26. Olive G, Jacques A, Phosphorus, Sulfur Silicon Relat. Elem. 2003 178 33
27. Szajnman S H., Montalvetti A, Wang Y, Docampo R, Rodriguez J B., Bioorg. Med. Chem. Lett. 2003 13 3231
28. For example:, Mimura M, Hayashida M, Nomiyama K, Ikegami S, Iida Y, Tamura M, Hiyama Y, Ohishi Y, Chem. Pharm. Bull. 1993 41 1971
29. Morioka M, Kamizono A, Takikawa H, Mori A, Ueno H, Kadowaki S, Nakao Y, Kato K, Umezawa K, Bioorg. Med. Chem. 2010 18 1143
30. Page P C. B., Moore J P. G., Mansfield I, McKenzie M J., Bowler W B., Gallagher J A., Tetrahedron 2001 57 1837
31. Page P C. B., McKenzie M J., Gallagher J A., Synth. Commun. 2002 32 211
32. Page P C. B., McKenzie M J., Gallagher J A., J. Org. Chem. 2001 66 3704
33. Duncan G D., Li Z.-M, Khare A B., McKenna C E., [nl] J. Org. Chem. 1995 60 7080
34. th, 2010 ICPC Wroclaw 2010 131
35. Degenhardt C R., Burdsall D C., J. Org. Chem. 1986 51 3488
36. 6): δ = 3.1 (dd, 3JPH = 35.1 Hz, 3JPH = 38.8 Hz) ppm. NMR spectral data were consistent with those described previously.12
37. 22
38. 2 (346.07): N, 8.09. Found: N, 8.40.
39. 2 (325.05): P, 11.07. Found: P, 10.89.
40. Frisch M J., Trucks G W., Schlegel H B., Scuseria G E., Robb M A., Cheeseman J R., Montgomery J A. Jr., Vreven T, Kudin K N., Burant J C., Millam J M., Iyengar S S., Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson G A., Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox E J., Hratchian H P., Cross J B., Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E., Yazyev O, Austin A J., Cammi R, Pomelli C, Ochterski J W., Ayala P Y., Morokuma K, Voth G A., Salvador P, Dannenberg J J., Zakrzewski V G., Dapprich S, Daniels A D., Strain M C., Farkas O, Malick D K., Rabuck A D., Raghavachari K, Foresman J B., Ortiz J V., Cui Q, Baboul A G., Clifford S, Cioslowski J, Stefanov B B., Liu G, Liashenko A, Piskorz P, Komaromi I, Martin R L., Fox D J., Keith T, Al-Laham M A., Peng C Y., Nanayakkara A, Challacombe M, Gill P M. W., Johnson B, Chen W, Wong M W., Gonzalez C, Pople J A., Gaussian 03, Revision d -02 Gaussian Inc. Pittsburgh 2003
41. Parr R G., Yang W, Functional Theory of Atoms and Molecules Breslow R Goodenough J B. Oxford University Press New York 1989
42. Becke A D., Phys. Rev. A 1988 38 3098
43. Becke [nl]A D., J. Chem. Phys. 1993 98 5648
44. Lee C, Yang W, Parr R G., Phys. Rev. B 1988 37 785
45. Flükiger P, Lüthi H P., Portmann S, Weber J, MOLEKEL 4.3 Swiss Center for Scientific Computing Manno (Switzerland) 2000-2002
46. Portmann S, Lüthi H P., Chimia 2000 54 766