Synthesis and antifungal activity of C-21 steroids with an aromatic D ring

Steroids

Volumn 78, Issue 7, 2013, Pages 644-650

  Sonego, Juan M ^a   Cirigliano, Adriana M ^a   Cabrera, Gabriela M ^a   Burton, Gerardo ^a   Veleiro, Adriana S ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Antifungal activity; Aromatic D ring; DABCO; Salpichrolides

Indexed keywords

STEROID;

ANTIFUNGAL ACTIVITY; AROMATIC D RING; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; FUSARIUM; FUSARIUM SOLANI; FUSARIUM VIRGULIFORME; NONHUMAN;

ANTIFUNGAL AGENTS; ERGOSTEROL; FUSARIUM; MOLECULAR STRUCTURE; STEROIDS;

FUSARIUM SOLANI; FUSARIUM VIRGULIFORME;

EID: 84877071013     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2013.02.003     Document Type: Article

References (23)

1. R.I. Misico, J.C. Oberti, V. Nicotra, G. Barboza, R. Gil, and G. Burton Withanolides and Related Steroids 2011 Progress in the Chemistry of Organic Natural Products Springer-Verlag Ed 127-229
2. A.S. Veleiro, J.C. Oberti, and G. Burton Atta-ur-Rahman Studies in Natural Products Chemistry Bioactive Natural Products vol. 32 2005 Elsevier Sciences Publishers Amsterdam p. 1019-52
3. M.J. Begley, L. Crombie, J.P. Ham, and D.A. Whiting Structures of three oxygenated 24-methyl-steroids (Nic-3, -7 and -1) from the insect repellent plant Nicandra physaloides (Solanaceae); X-Ray analysis of Nic-3 acetate and Nic-1 Ethyl Ether J C S Perkin I 1976 296 302
4. M.J. Begley, L. Crombie, P.J. Ham, and D.A. Whiting Constitution of four novel methyl steroid relatives (ring-D aromatic) from the insect repellent plant nicandra physaloides; X-Ray analyis of Nic-10 J C S Chem Commun 1972 1250 1251
5. R.B. Bates, and D.J. Eckert Nicandrenone, an insecticidal plant steroid derivative with ring D aromatic J Am Chem Soc 94 1972 8258 8260
6. M.C. Tettamanzi, A.S. Veleiro, J.R. de la Fuente, and G. Burton Withanolides from Salpichroa origanfolia J Nat Prod 64 2001 783 786
7. A.S. Veleiro, J.C. Oberti, and G. Burton A ring-D aromatic withanolide from Salpichroa origanifolia Phytochemistry 31 1992 935 937
8. G. Mareggiani, M.I. Picollo, E. Zerba, G. Burton, M.C. Tettamanzi, M.O.V. Benedetti-Doctorovich, and A.S. Veleiro Antifeedant activity of withanolides from Salpichroa origanifolia on Musca domestica J Nat Prod 63 2000 1113 1116
9. G. Mareggiani, M.I. Picollo, A.S. Veleiro, M.C. Tettamanzi, M.O.V. Benedetti-Doctorovich, G. Burton, and E. Zerba Response of Tribolium castaneum (Coloptera, Tenebrionidae) to Salpichroa origanifolia Withanolides J Agric Food Chem 50 2002 104 107 (Pubitemid 34038515)
10. S. Bado, G. Maregianni, N. Amiano, G. Burton, and A.S. Veleiro Lethal and sublethal effects of withanolides from Salpichroa origanifolia and Analogues on Ceratitis capitata J Agric Food Chem 52 2004 2875 2878
11. R.P. Machin, A.S. Veleiro, V.E. Nicotra, J.C. Oberti, and J.M. Padrón Antiproliferative activity of withanolides against human breast cancer cell lines J Nat Prod 73 2010 966 968
12. T. Aoki, K. ÓDonnell, and M.M. Sacndiani Sudden death syndrome of soybean in South America is caused by four species of Fusarium: Fusarium brasiliense sp. nov., F. cuneirostrum sp. nov., F. tucumaniae, and F. virguliforme Mycoscience 46 2005 162 183 (Pubitemid 40865708)
13. B.M. Stoltz, T. Kano, and E.J. Corey Enantioselective total synthesis of nicandrenones J Am Chem Soc 122 2000 9044 9045
14. H.K. Gill, R.W. Smith, and D.A. Whiting Ring D expansion and aromatisation in the biosynthesis of Nic-1, an antifeedant steroid from Nicandra physaloides J Chem Soc Perkin Trans I 1990 2989 2993
15. B. Blumbach, D.A. Hammond, and D.A. Whiting Synthetic approaches to the ring system of nicandra (Benzenoid Ring D) J Chem Soc Perkin Trans I 1986 261 268
16. P.H. Di Chenna, A. Ferrara, A.A. Ghini, and G. Burton Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides J Chem Soc Perkin Trans I 2002 227 231 (Pubitemid 35188276)
17. M. Bakavoli, M. Rahimizadeh, H. Eshgi, A. Shiri, Z. Ebrahimpour, and R. Takjoo Synthesis, characterization and structure of DBU-hydrobromide-perbromide: a novel oxidizing agent for selective oxidation of alcohols to carbonyl compounds Bull Korean Chem 31 2010 949 952
18. M.M. Heravi, F. Derikvand, M. Ghassemzadeh, and B. Neumüller Synthesis, characterization and structure of a tetrameric DABCO-bromine complex: a novel oxidizing agent for oxidation of alcohols to carbonyl compounds Tetrahedron Lett 46 2005 6243 6245 (Pubitemid 41140171)
19. Jacob MR, Walker LA. Natural products and antifungal drug discovery. In: Ernst EJ, Rogers PD editors Methods in molecular medicine, antifungal agents: methods and protocols, first ed. Humana Press Inc, Totowa, NJ, 2005. vol. 118. p. 83-110.
20. F. Hadacek, and H. Greger Testing of antifungal natural products: methodologies, comparability and assay choice Phytochem Anal 11 2000 137 147 (Pubitemid 30248992)
21. A. Espinel-Ingroff, T.M. Kerkering, P.R. Goldson, and S. Shadomy Comparison study of broth macrodilution and microdilution antifungal susceptibility tests J Clin Microbiol 29 1991 1089 1094
22. P. Choay, C. Monneret, G. Narcisse, and F. Bakri-Logeais Synthèse de dérivés des D-homo androstane et pregnane. Recherche d́une activité anti-androgène Eur J Med Chem Chimica Therapeutica 15 1980 419 423 (Pubitemid 11215472)
23. E. Ma, H. Kim, and E. Kim Epoxidation and reduction of cholesterol, 1,4,6-cholestatrien-3-one and 4,6-cholestadien-3-ol Steroids 70 2005 245 250 (Pubitemid 40387378)