A practical synthesis of thio-bisphosphonic acids for the treatment of arthritis, based on the chemistry of tetraethyl methylene-1,1-bisphosphonate

Letters in Organic Chemistry

Volumn 3, Issue 8, 2006, Pages 634-639

  Abdou, Wafaa M ^a   Khidre, Maha D ^a   Sediek, Ashraf A ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Arthritis inflammatory; Cyclic and acyclic cis disulfides; Shiff bases; Sulfur containing bisphosphonic acids

Indexed keywords

EID: 33750046615     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806778559536     Document Type: Article

References (31)

1. Russell, R.G. Phos. Sulf. and Silicon, 1999, 144-146, 793-830, a review and references therein cited.
2. Fleisch, H. Bisphosphonates in Bone Diseases. From the laboratory to the Patient, 3rd Edn. Parthenon Publishing Group, New York, NY, 1997.
3. Francis, R.M.A, Curr. Therp. Res. (Review) 1998, 56, 831-851.
4. Fleisch, H. Breast Cancer Res., 2002, 4, 30-34.
5. (a) Siestema, W.K.; Ebetino, F.H. Expert. Opin. Invest. Drugs, 1994, 3, 1255-1276; Chem. Abstr., 1995, 122, 3;
6. (b) Almstead, N.G.; Dansereay, S.M.; Francis, M.D.; Snider, C.M.; Ebetino, F.H. Phos. Sulf. Silicon, 1999, 144-146, 325-328.
7. (a) Abdou, W.M.; Ganoub, N.A.; Fahmy, A.F.; Shaddy, A.A. Monatsh. Chem., 2006, 137, 105-116;
8. (b) Abdou, W.M.; Ganoub, N.A.; Elkhoshnieh, Y.O. Synlett, 2003, 785-790.
9. Inhibition of MMPs by bisphosphonates has previously been disclosed. See: Teronen, O.; Kontinnen, Y.T.; Lindqvist, C.; Salo, T.; Lauhio, A.; Ding, Y.; Santavirta, S.; Sorsa, T. J. Dent. Res. 1997, 76, 1529-1537, Chem. Abstr., 1997, 127, 88.
10. (a) Khidre, M.D.; Abdou, W.M. Z. Naturforsch., accepted for publication;
11. (b) Kamel, A.A.; Abdou, W.M. J. Heterocyclic Chem., 2005, 42, 103-107;
12. (c) Abdou, W.M.; Khidre, M.D.; Kamel, A.A. Heterocycl. Comm., 2004, 10, 217-222;
13. (d) Abdou, W.M. Phos. Sulf. Silicon, 1999, 144, 393-396;
14. (e) Abdou, W.M.; Ganoub, N.A.F. Phos. Sulf. Silicon, 1995, 105, 63-71;
15. (f) Abdou, W.M.; Hennawy, I.T.; Elkhoshnieh, Y.O. J. Chem. Res. (S), 1995, 50-51; (M), 1995, 442-451;
16. (g) Abdou, W.M.; Hennawy, I.T. Phos. Sulf. Silicon, 1994, 89, 105-112;
17. (h) Abdou, W.M.; Yakout, E.S.M.A.; Said, M.M. Int. Sulfur Lett., 1993, 17, 33-43;
18. (i) Abdou, W.M.; Yakout, E.S.M.A. Tetrahedron, 1993, 49, 6411-6418.
19. 4. After removal of the solvent, under vacuum, the resulting residue was chromatographed on silica gel (n-hexane/AcOEt) to give compounds 4a, 6a, 9a, 10a, and 12a. Percentage yields; physical and spectral data of the products are listed in Tables 1 and 2.
20. (a) Galli, R. J. Org. Chem., 1987, 52,5349-5359;
21. (b) Trebaul, C.; Teste, J. Bull. Soc. Chim (France), 1969, 2456.
22. Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.O. Org. Synth., 1984, 62, 158-164.
23. (a) Yoshida, Z.; Yoneda, S.; Kawase, T.; Inaba, M. Tetrahedron Lett., 1978, 1285-1288;
24. (b) Boulos, L.S.; Yakout, E.S.M.A. Phos. Sulf. Silicon, 1993, 84, 35-38.
25. Field, L.; Banks, C.H. J. Org. Chem. 1975, 40, 2774-2779.
26. Ebetino, F.H.; Dansereau, S.M. In Bisphosphonates on Bones, Bijivoet, O.; Fleisch, H.A.; Canfield, R.E.; Russell, R.G.G. (Eds), Elsvier, Amesterdam, 1995; pp. 139-154.
27. 2, the solid was filtered, washed twice with ethanol to give the required thio-bisphosphonic acid 4b, 6b, 9b, 10b, or 12b. Percentage yields; physical and spectral data are listed in Tables 1 and 2.
28. Takanisha, K; Chiro, H.; Kawabe, N. PCT Int. Appl. WO 9419, 359 (Cl. C07F9/ 40)1994 JP; Chem. Abstr., 1995, 123, 1152.
29. Wilder, L.; Jaeggl, K.A.; Green, J.R. Phos. Sulf. Silicon, 1999, 144-146, 5-8.
30. 3), dried, and evaporated till dryness. The precipitate was washed with EtOH, and filtered to give the BP 14a. Hydrolysis of 14a with conc. HCl (15 h) as previously described [15] yielded 14b. Physical and spectroscopic results of 14a and 14b are given in Tables 1 and 2.
31. Nugent, R.A.; Murphy, M.; Schlachtar, S.T.; Dunn, C.J.; Smith, R.J.; Staite, N.D.; Galinet, L.A.; Shields, S.K.; Aspar, D.G.; Richard, K.A.; Rohloff, N.A. J. Med. Chem., 1993, 36, 134-139.