Novel steroidal penta- and hexacyclic compounds derived from 12-oxospirostan sapogenins

Steroids

Volumn 75, Issue 13-14, 2010, Pages 1127-1136

  Pérez Díaz, José Oscar H ^a   Vega Baez, José Luis ^b   Sandoval Ramírez, Jesús ^b   Meza Reyes, Socorro ^b   Montiel Smith, Sara ^b   Farfán, Norberto ^c   Santillan, Rosa ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^c Universidad Nacional Autonoma de Mexico Facultad de Quimica   (Mexico)

Author keywords

12 Oxosapogenins; Intramolecular cyclocondensation; Polycyclic steroids

Indexed keywords

12 OXOSPIROSTAN SAPOGENIN DERIVATIVE; SAPOGENIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77957253942     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2010.07.008     Document Type: Article

References (47)

1. A.L. Harvey Natural products in drug discovery Drug Discov Today 13 2008 894 901
2. G.R. Pettit, M. Inoue, Y. Kamano, D.L. Herald, C. Arm, and C. Dufresne Isolation and structure of the powerful cell growth inhibitor cephalostatin 1 J Am Chem Soc 110 1988 2006 2007 (Pubitemid 18090678)
3. J.R. Williams, H. Gong, N. Hoff, O.I. Olubodun, and P.J. Caroll α-Hydroxylation at C-15 and C-16 in cholesterol: synthesis of (25R)-5α-cholesta-3β,15α,26-triol and (25R)-5α-cholesta- 3β,16α,26-triol from diosgenin Org Lett 6 2004 269 271 (Pubitemid 38175765)
4. S. Lee, T.G. LaCour, D. Lantrip, and P.L. Fuchs Redox refunctionalization of steroid spiroketals. Structure correction of ritterazine M Org Lett 4 2002 313 316
5. P. Trouillas, C. Corbire, B. Liagre, J.L. Duroux, and J.L. Beneytout Structure-function relationship for saponin effects on cell cycle arrest and apoptosis in the human 1547 osteosarcoma cells: a molecular modelling approach of natural molecules structurally close to diosgenin Bioorg Med Chem 13 2005 1141 1149 (Pubitemid 40164598)
6. R.E. Marker, T. Tsukamoto, and D.L. Turner Sterols C. Diosgenin J Am Chem Soc 62 1940 2525 2532
7. A.F.B. Cameron, R.M. Evans, J.C. Hamlet, J.S. Hunt, P.G. Jones, and A.G. Long Studies in the synthesis of cortisone. Part XII. Improvements in the conversion of sapogenins into pregnan-20-ones J Chem Soc 1955 2807 2816
8. J. Elks, G.H. Phillips, T. Walker, and L.J. Wyman Studies in the synthesis of cortisone. Part XV. Improvements in the conversion of hecogenin into 3β:12β-diacetoxy-5α:25D-spirostan-11-one and a study of the isomeric 11:12 ketols J Chem Soc 1956 4330 4344
9. J.E. Aho, P.M. Pihko, and T.K. Rissa Nonanomeric spiroketals in natural products: structures, sources, and synthetic strategies Chem Rev 105 2005 4406 4440
10. 1,4,9(11)-3-ketosteroids by selective dehydrogenation of 3-hydroxy-12-ketosteroids Chem Lett 27 1998 1207 1208 (Pubitemid 128384707)
11. S. Kim, S.C. Sutton, C. Guo, T.G. LaCour, and P.L. Fuchs Synthesis of the north 1 unit of the cephalostatin family from hecogenin acetate J Am Chem Soc 121 1999 2056 2070 (Pubitemid 129540936)
12. S.T. Phillips, and M.D. Shair Syntheses of the eastern halves of ritterazines B, F, G, and H, leading to reassignment of the 5,5 spiroketal stereochemistry of ritterazines B and F J Am Chem Soc 129 2007 6589 6598
13. C. Djerassi, H.J. Ringold, and G. Rosenkranz Steroidal sapogenins. XXXVII. Experiments in the hecogenin series. (Part 6). Conversion to cortisone J Am Chem Soc 76 1954 5533 5536
14. N. Kongkathip, B. Kongkathip, and N. Noimai Synthesis of betamethasone from the waste of Thai Agave Sisalana Synth Commun 36 2006 865 874 (Pubitemid 43323237)
15. P.A. McCarthy, M.P. DeNinno, L.A. Morehouse, C.E. Chandler, F.W. Bangerter, and T.C. Wilson 11-Ketotigogenin cellobioside (Pamaqueside): a potent cholesterol absorption inhibitor in the hamster J Med Chem 39 1996 1935 1937 (Pubitemid 26163242)
16. S.I. Gohzu, and M. Tada Regioselective reduction of polyketones on silica gel surface with borane-trimethylamine complex Chem Lett 15 1986 61 64
17. J. Fried, and J.A. Edwards Organic reactions in steroid chemistry, vol. I 1972 Van Nostrand Reinhold Company New York, USA
18. A.E. Leontjev, L.L. Vasiljeva, and K.K. Pivnitsky Reduction of steroidal ketones with amine-boranes Russ Chem Bull Int Ed 53 2004 703 708
19. R.E. Marker, D.L. Turner, R.B. Wagner, P.R. Ulshafer, H.M. Crooks, and E.L. Wittle Sterols. CXVII. Sapogenins. XLVI. The structure of pseudosapogenins J Am Chem Soc 63 1941 774 777
20. J.A. Zderic, L. Cervantes, and M.T. Galvan Sapogenins. XLI. A new reaction of the spiroketal side chain J Am Chem Soc 84 1962 102 106
21. A.G. González, C.G. Francisco, R. Freire, R. Hernández, J.A. Salazar, and E. Suárez Regioselective opening of ring E in spirostan sapogenins Tetrahedron Lett 17 1976 1325 1328
22. A. Tobari, H. Miyamae, A. Nagasawa, J. Koyanagi, M. Kawase, and S. Saito Cyanoglycosylation accompanied by ring-opening of spirostanols Heterocycles 53 2000 1745 1764
23. A.K. Singh, and D.N. Dhar Regioselective cleavage of the "E" ring in diosgenin Bull Soc Chim Belg 90 1981 981 982
24. J. Sandoval-Ramírez, A. Castro-Méndez, S. Meza-Reyes, F. Reyes-Vázquez, R. Santillan, and N. Farfán Preparation of 22,26-epoxycholest-22-ene steroids. Novel transformation of the side chain in sapogenins Tetrahedron Lett 40 1999 5143 5146 (Pubitemid 29307877)
25. S. Rincón, R.E. Del Río, J. Sandoval-Ramírez, S. Meza-Reyes, S. Montiel-Smith, and M.A. Fernández A new route for the preparation of the 22,23-dioxocholestane side chain from diosgenin and its application to the stereocontrolled construction of the 22R,23S-diol function Tetrahedron 62 2006 2594 2602
26. J. Sandoval-Ramírez, S. Meza-Reyes, R.E. del Río, G. Hernández-Linares, A. Suarez-Rojas, and S. Rincón Regioselective cleavage of rings E and F in sarsasapogenin Steroids 68 2003 199 204 (Pubitemid 36279171)
27. M.A. Fernández-Herrera, J. Sandoval-Ramírez, S. Meza-Reyes, and S. Montiel-Smith Side-chain opening of steroidal sapogenins to form 22-oxocholestanic skeletons. An approach to analogues of the aglycone of the potent anticancer agent OSW-1 J Mex Chem Soc 53 2009 126 130
28. M.A. Fernández-Herrera, H. López-Muñoz, J.M.V. Hernández-Vázquez, M. López-Dávila, M.L. Escobar-Sánchez, and L. Sánchez-Sánchez Synthesis of 26-hydroxy-22-oxocholestanic frameworks from diosgenin and hecogenin and their in vitro antiproliferative and apoptotic activity on human cervical cancer CaSki cells Bioorg Med Chem 18 2010 2474 2484
29. T.G. LaCour, Z. Tong, and P.L. Fuchs Consequences of acid catalysis in concurrent ring opening and halogenation of spiroketals Org Lett 1 1999 1815 1818
30. G.M. Sheldrick SHELXL-86. A program for crystal structure solution 1986 University of Göttingen Germany
31. P.W. Betteridge, J.R. Carruthers, R.I. Cooper, K. Prout, and D.J. Watkin Crystals version 12: software for guided crystal structure analysis J Appl Cryst 36 2003 1487
32. C.L. Wilson Reactions of furan compounds. Part II. Fission of the tetrahydrofuran and the tetrahydropyran ring J Chem Soc 1945 48 51
33. K.O. Christie, and A.E. Pavlath The chemistry of carbonyl chloride fluoride. I. The ring opening of cyclic ethers with carbonyl chloride fluoride J Org Chem 30 1965 1639 1643
34. V. Schliephake, K.H. Mix, and H.G. Wagner Investigations of the kinetics of the reactions of tetrahydrofurane, tetrahydropyrane, cyclopentanone and cyclohexanone with atomic oxygen Z Phys Chem Neue Folge 150 1986 1 15
35. H.E. Wirth, and P.I. Slick The relative basicities of ethers J Phys Chem 66 1962 2277 2279
36. P.K. Agrawal, D.C. Jain, and A.K. Pathak NMR Spectroscopy of steroidal sapogenins and steroidal saponins: an update Magn Reson Chem 33 1995 923 953
37. P.K. Agrawal, D.C. Jain, R.K. Gupta, and R.S. Thakur Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins Phytochemistry 24 1985 2479 2496
38. K.M. Wellman, and F.G. Bordwell Magnetic shielding of alpha protons by the carbonyl group in cyclohexanones Tetrahedron Lett 4 1963 1703 1708
39. D. Danneels, and M. Anteunis Stereochemical aspects of proton chemical shift. II. The influence of the hydroxyl substituent on the chemical shift of ring protons in cyclohexane derivatives Tetrahedron Lett 16 1975 687 690
40. E.A. Basso, C. Kaiser, R. Rittner, and J.B. Lambert Axial/equatorial proportion for 2-substituted cyclohexanones J Org Chem 58 1993 7865 7869
41. 1H spectra of the steroid hormones, their hydroxylated derivatives, and related compounds J Chem Soc Perkin Trans 2 1990 1567 1594
42. J.N. Shooley, and M.T. Rogers Nuclear magnetic resonance spectra of steroids J Am Chem Soc 80 1958 5121 5135
43. M.F. Grenier-Loustalot, A. Lectard, F. Metras, and A. Forchioni Etude de l'influence de la nature et de l'orientation d'un substituant (Cl, CO) sur les déplacements chimiques en série tertiobutyl-4 cyclohexanonique par RMN protonique haut champ Org Magn Reson 10 1977 92 97
44. 13C olefinic carbon shieldings in sterols and related cyclic compounds Chem Phys Lipids 25 1979 49 68
45. 13C nuclear magnetic resonance spectra of norethisterone using two-dimensional nuclear magnetic resonance spectroscopy J Chem Soc Perkin Trans 2 1984 1755 1759
46. F.H. Allen, D.G. Watson, L. Brammer, A.G. Orpen, and R. Taylor International tables for crystallography, vol. C 3rd ed. 2006 Kluwer Academic Publication Dordrecht 790 811 [Chapter 9.5]
47. A. Castro-Méndez, J. Sandoval-Ramírez, and S. Berns A derivative of diosgenin: (25R)-23-acetyl-3β-bromo-16β-acetoxy-22,26- epoxy-5α-cholest-22-en-6-one Acta Cryst E 58 2002 606 608