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Short Note

4α,14α,Dimethyl-5α-cholest-8-en-3-one thiosemicarbazone

by
Noureddine Mazoir
1,*,
My Youssef Ait Itto
1,
Matías Reina Artiles
2 and
Ahmed Benharref
1
1
Laboratoire de Chimie des Substances Naturelles, Université Cadi Ayyad, Faculté des Sciences Semlalia, B.P: 2390. Marrakech. Maroc
2
Instituto de Productos Naturales y Agrobiología, IPNA-CSIC, La Laguna, Tenerife, Spain
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(6), M504; https://doi.org/10.3390/M504
Submission received: 1 August 2005 / Accepted: 17 October 2006 / Published: 1 December 2006
Versions Notes

Molbank 2006 m504 i001
The compound 2 was prepared from equimolecular quantity of 1 (1g, 2.43 mmol), derivative triterpene resulting from Euphorbia officinarum1, and thiosemicarbazide2,3 dissolved in ethanol with several drops of conc. H2SO4. The mixture was heated at reflux for 5h, and evaporated under reduced pressure. The residue was purified on silica gel column using hexane: ethyl acetate (90:10) as eluent yielded compound 2 (0.99g, 2.06mmol) in 85% yield.
Melting point: 212-213 °C (Hexane)
MS (EI, 70eV): 485 (M+.)
1H NMR (300 MHz, CDCl3) d(ppm): 6.33 (NH); 7.25 (NH2); 8.74 (SH); 0.70 (3H-18, s); 0.96 (3H-19, s); 0.88 (3H-21, d, J = 6 Hz); 0.85 (3H-26, d, J = 2 Hz ); 0.86 (3H-27, d, J = 2 Hz ); 0.87 (3H-28, s); 1.20 (3H-29, d, J = 6 Hz ).
13C NMR (75 MHz, CDCl3) d (ppm): 36.50 (C-1); 37.35 (C-2); 159.35 (C-3) ; 50.58 (C-4); 49.98 (C-5); 21.75 (C-6); 28.12 (C-7); 132.35 (C-8); 135.73 (C-9); 36.36 (C-10); 21.55 (C-11); 25.45 (C-12); 44.54 (C-13); 49.75 (C-14); 30.86 (C-15); 29.81 (C-16); 46.10 (C-17); 15.82 (C-18); 18.15 (C-19); 36.14 (C-20); 18.65 (C-21); 36.56 (C-22); 24.35 (C-23); 32.41 (C-24); 34.58 (C-25); 21.72 (C-26); 21.92 (C-27); 24.22 (C-28); 12.25 (C-29); 106.12 (C-30); 179.18 (C=S).
MS (m/z): 485 (20%), 395 (42%), 282 (65%).

Supplementary Materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgments

We would like to thank Pr. A. Idmessaaoud for helpful discussions.

References

  1. Benharref, A.; Lavergne, J.-P. Bull. Soc. Chim. Fr. 1985, 965–972.
  2. Beatriz, N.B.; et al. Arkivok. 2002, 14–23.
  3. Ourhriss, N.; Giorgi, M.; Mazoir, N.; Benharref, A. Acta Cryst. 2005, C61, o699–o701.

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MDPI and ACS Style

Mazoir, N.; Itto, M.Y.A.; Artiles, M.R.; Benharref, A. 4α,14α,Dimethyl-5α-cholest-8-en-3-one thiosemicarbazone. Molbank 2006, 2006, M504. https://doi.org/10.3390/M504

AMA Style

Mazoir N, Itto MYA, Artiles MR, Benharref A. 4α,14α,Dimethyl-5α-cholest-8-en-3-one thiosemicarbazone. Molbank. 2006; 2006(6):M504. https://doi.org/10.3390/M504

Chicago/Turabian Style

Mazoir, Noureddine, My Youssef Ait Itto, Matías Reina Artiles, and Ahmed Benharref. 2006. "4α,14α,Dimethyl-5α-cholest-8-en-3-one thiosemicarbazone" Molbank 2006, no. 6: M504. https://doi.org/10.3390/M504

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