Facile one-pot synthesis of thio and selenourea derivatives: A new class of potent urease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 22, 2007, Pages 6387-6391

  Sivapriya, Kirubakaran ^a   Suguna, Perumal ^a   Banerjee, Arun ^a   Saravanan, Vadivelu ^a   Rao, Desirazu N ^a   Chandrasekaran, Srinivasan ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Selenourea; Tetraselenotungstate; Tetrathiomolybdate; Thiourea; Urease inhibition

Indexed keywords

AMINE; REAGENT; SELENIUM DERIVATIVE; TETRATHIOMOLYBDIC ACID; THIOL DERIVATIVE; TUNGSTEN DERIVATIVE; UREA DERIVATIVE; UREASE; UREASE INHIBITOR;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; ONE POT SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CANAVALIA; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLYBDENUM; ORGANOSELENIUM COMPOUNDS; THIOUREA; UREA; UREASE;

CANAVALIA ENSIFORMIS;

EID: 35148879585     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.085     Document Type: Article

References (21)

1. Phuong T., Khac-Minh T., Van Ha N.T., and Phuong H.T.N. Bioorg. Med. Chem. Lett. 14 (2004) 653 and references cited there-in
2. Caujolle R., Amarouch H., Payard M., Loiseau P.M., Bories C., Gayral P., Linas M.D., and Seguela J.P. Eur. J. Med. Chem. 30 (1995) 801
3. Ozcan M., Dehri I., and Erbil M. Appl. Surf. Sci. 236 (2004) 155
4. Hiroshi K., Keiko T., Masami A., Emiko M., Kayoko M., and Toshiyuki A. Bioorg. Med. Chem. Lett. 9 (1999) 1347
5. Cho S.I., Koketsu M., Ishihara H., Matsushita M., Nairn A.C., Fukazawa H., and Uehara Y. Biochim. Biophys. Acta 1475 (2000) 207
6. Matsuno K., Nakajima T., Ichimura M., Neill A.G., Yu J.-C., Lokker N.A., Ushiki J., Ide S., Oda S., and Nomoto Y. J. Med. Chem. 45 (2002) 4513
7. Koketsu M., Suzuki N., and Ishihara H. J. Org. Chem. 64 (1999) 6473 and references cited therein
8. Rasmussen C.R., Villani F.J., Weaner L.E., Reynolas B.E., Hood A.R., Hecker L.R., Nortey S.O., Hanslin A., Costanzo M.J., Powell E.T., and Molinari A.J. Synthesis (1988) 456
9. Ishihara H., Koketsu M., Fukuta Y., and Nada F. J. Am. Chem. Soc. 123 (2001) 8408
10. Koketsu M., Fukuta Y., and Ishihara H. J. Org. Chem. 67 (2002) 1008 and references cited there-in
11. Viehe H.G., and Janousek Z. Angew. Chem., Int. Ed. Engl. 10 (1971) 573
12. Prabhu K.R., Devan M.N., and Chandrasekaran S. Synlett (2002) 1762
13. Saravanan V., Porhiel E., and Chandrasekaran S. Tetrahedron Lett. 44 (2003) 2257
14. Saravanan V., Mukherjee C., Das S., and Chandrasekaran S. Tetrahedron Lett. 45 (2004) 681
15. CCDC numbers for compound 16a: CCDC 642511, Compound 14b: CCDC 642510, compound 12a: CCDC 644845: Crystallographic data (excluding structure factors) for the structure in this paper have been deposited to the Cambridge Crystallographic Data Centre as supplementary publication. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/.
16. The reason for the instability of compounds 9b, 11b and 12b is not clear.
17. Mobley H.L.T., Island M.D., and Hausinger R.P. Microbiol. Rev. 59 (1995) 451 and references cited there-in
18. Todd M.J., and Hausinger R.P. J. Biol. Chem. 264 (1989) 15835
19. 19
20. A few of the urea derivatives have not been tested for their activity due to their poor solubility in the buffer solution.
21. Lopreore C., and Byers L.D. Arch. Biochem. Biophys. 349 (1998) 299