Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 521-525

  Jones, Ian L ^a   Schofield, Daniel J ^a   Strevens, Robert R ^a   Horton, Peter N ^a   Hursthouse, Michael B ^a   Tomkinson, Nicholas C O ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; ANDROGEN RECEPTOR; ANDROSTANOLONE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; ESTRADIOL; GLYOXYLIC ACID; GLYOXYLIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; OXAMIDE; OXOAMIDE; OXYGEN DERIVATIVE; STEROID;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; FRIEDEL CRAFTS REACTION; SYNTHESIS;

TETRA;

EID: 33845633774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.139     Document Type: Article

References (24)

1. O'Malley B.W. Hormones and Signalling (1998), Academic Press, San Diego
2. In: Parker M.G. (Ed). Steroid Hormone Action (1993), IRL Press, Oxford
3. Saraber F.C.E., and de Groot A. Tetrahedron 62 (2006) 5363-5383
4. Bijoy P., Naik R.G., Shivakumar U., and Rao G.S.R. J. Ind. Inst. Sci. 74 (1994) 519-541
5. Zeelen F.J. Nat. Prod. Rep. 11 (1994) 607-612
6. Groen M.B., and Zeelen F.J. Recl. Trav. Chim. Pays-Bas 105 (1986) 465-487
7. Hoffmann M., Rychlewska U., and Warzajtis B. Cryst. Eng. Commun. 7 (2005) 260-265
8. Martínez-Martínez F.J., Padilla-Martínez I.I., Brito M.A., Geniz E.D., Rojas R.C., Saavedra J.B.R., Höpfl H., Tlahuextl M., and Conteras R. J. Chem. Soc., Perkin Trans. 2 (1998) 401-406 and references cited therein
9. Dugave C., and Demange L. Chem. Rev. 103 (2003) 2475-2532
10. Clayden J. Synlett (1998) 810-816
11. For related work using the urea motif to engender molecular rigidity, see:. Bridgeman E., Cavill J.L., Schofield D.J., Wilkins D.S., and Tomkinson N.C.O. Tetrahedron Lett. 46 (2005) 8521-8524
12. 13C NMR, MS and HRMS.
13. Gautier E.C.L., Graham A.E., McKillop A., Standen S.P., and Taylor R.J.K. Tetrahedron Lett. 38 (1997) 1881-1884
14. Stollé R. Chem. Ber. 47 (1914) 1130-1132
15. Stollé R., and Knebel E. Chem. Ber. 54 (1921) 1213-1220
16. For a related strategy in the preparation of ureas, see:. Bridgeman E., and Tomkinson N.C.O. Synlett (2006) 243-246
17. Temeriusz A., Rowińska M., and Piekarska-Bartoszewicz B. Carbohydr. Res. 340 (2005) 1656-1660
18. Temeriusz A., Anulewicz R., Wawer I., Krygowski T.M., Piekarska-Bartoszewicz B., and Rowińska M. Carbohydr. Res. 334 (2001) 71-79
19. Rastegar M.F., Todd E.K., Tang H., and Wang Z.Y. Org. Lett. 6 (2004) 4519-4522
20. Neveux M., Bruneau C., Lecolier S., and Dixneuf P.H. Tetrahedron 49 (1993) 2629-2640
21. Katritzky A.R., Levell J.R., and Pleynet D.P.M. Synthesis (1998) 153-156
22. Mitlak B.H., and Cohen F.J. Drugs 57 (1999) 653-663
23. -3, respectively. Crystallographic data (excluding structure factors) for structure 25 has been deposited with the Cambridge Crystallographic Data Centre as supplementary Publication Number 620459. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
24. Pereira do Jesus-Tran K., Cote P.-L., Cantin L., Blanchet J., Labrie F., and Breton R. Prot. Sci. 15 (2006) 987-999