Synthesis and spectroscopic data analyses of 5β-cholane derivatives

Acta Pharmaceutica

Volumn 56, Issue 3, 2006, Pages 369-375

  Nahar, Lutfun ^a   Sarker, Satyajit D ^b   Turner, Alan B ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b UNIVERSITY OF ULSTER   (United Kingdom)

Author keywords

Lithocholic acid; NMR; Reduction; Steroids; Tosylation

Indexed keywords

3ALPHA TOSYLOXY 5BETA CHOLAN 24 OL; 5BETA CHOLAN 24 OL; 5BETA CHOLAN 24 YL TOSYLATE; 5BETA CHOLANE DERIVATIVE; CHOLANE DERIVATIVE; LITHOCHOLIC ACID; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DATA ANALYSIS; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SPECTROSCOPY;

EID: 33748864533     PISSN: 13300075     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. R. F. Witzmann, Steroids-Key to Life, Van Nostrand Reinhold, New York 1981.
2. Y. X. Li and J. R. Dias, Dimeric and oligomeric steroids, Chem. Rev. 97 (1997) 283-304.
3. P. Fernandes, A. Cruz, B. Angelova, H. M. Pinheiro and J. M. S. Cabrai, Microbial conversion of steroid compounds: recent developments, Enzyme Microb. Tech. 32 (2003) 688-705.
4. P. J. Cox, L. Nahar and A. B. Turner, Synthesis and X-ray crystal structure of 5β-cholan-24-yl chloride, J. Chem. Res. (S) 2001, 162-164.
5. L. Nahar and A. B. Turner, Synthesis of 3β,6α-dihydroxy- 5α-cholan-23-one, Tetrahedron 59 (2003) 8623-8628.
6. L. Nahar and A. B. Turner, Synthesis of ester-linked lithocholic acid dimers, Steroids 68 (2003) 1157-1161.
7. L. Nahar, S. D. Sarker, P-K. Li and A. B. Turner, Synthesis of new estrone derivatives using excess oxalyl chloride, Chem. Nat. Compd. 40 (2004) 50-53.
8. L. Nahar and A. B. Turner, Synthesis of dinorcholane and 5β-cholane derivatives, J. Chem. Res. (S) 2004, 329-332.
9. T. Iida, T. Momose, F. C. Chang, J. Goto and T. Nambara, Potential bile-acid metabolites. 15. synthesis of 4-beta-hydroxylated bile-acids - unique bile-acids in human-fetal bile, Chem. Pharm. Bull. 37 (1989) 3323-3329.
10. 13C NMR spectroscopy, Magn. Reson. Chem. 24 (1986) 185-189.
11. R. T. Blickenstaff and F. C. Chang, Seroflocculating steroids. V. Reduction of the bile acid side chain, J. Am. Chem. Soc. 80 (1958) 2726-2729.
12. R. Breslow, S. Baldwin, T. Flechtner, P. Kalicky, S. Lin and W. Washburn, Remote oxidation of steroids by photolysis of attached benzophenone groups, J. Am. Chem. Soc. 95 (1973) 3251-3259.
13. M. Cushman, W. M. Golebiewski, Y. Pommier, A. Mazumder, D. Reymen, E. De Clercq, L. Graham and W. G. Rice, Cosalane analogs with enhanced potencies as inhibitors of HIV-1 protease and integrase, J. Med. Chem. 38 (1995) 443-452.