Molbank 2006, M504

http://www.mdpi.org/molbank/

 

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

 

Noureddine Mazoir,*1 My Youssef Ait Itto,1 Matías Reina Artiles2 and Ahmed Benharref1

 

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

E-mail: [email protected]

*Author to whom correspondence should be addressed

 

Received: 1 August 2005 / Accepted: 17 October 2006 / Published: 1 December 2006

 

Keywords: Euphorbia officinarum, latex, thiosemicarbazide

 


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%).

 

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 and Benharref, A. Acta Cryst. 2005, C61, o699-o701.

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