Transformation of aminosteroids into pharmacologically active amides of phenolic acids

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 54, Issue 1-2, 1999, Pages 65-69

  Todorova, Daniela ^a   Tupova, Maria ^a   Zapreva, Veneta ^a   Milkova, Tsenka ^a   Kujumdjiev, Atanas ^a  

^a BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

Author keywords

3 and 3 amino (2' aminoethyl)cholest 5 en; 5 cholestan 3 yl amine; 5 cholestan 3 yl amine; Amides of Cinnamic Acid Derivatives; Antibacterial Activity

Indexed keywords

1 HYDROXYBENZOTRIAZOLE; 3ALPHA AMINO (2' AMINOETHYL) CHOLEST 5 EN; 3ALPHA CHOLESTANYLAMINE; 3BETA AMINO (2' AMINOETHYL) CHOLEST 5 EN; 3BETA CHOLESTANYLAMINE; 4 HYDROXYCINNAMIC ACID; BACTERICIDAL ACTIVITY; DICYCLOHEXYLCARBODIIMIDE; DRUG SYNTHESIS; STAPHYLOCOCCUS AUREUS;

EID: 0033032405     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-1999-1-212     Document Type: Article

References (17)

1. Baters E., Monroy G. and Ringold H. J. (1961), Steroids CLVII '6-aminoandrostanes. J.Org.Chem. 26, 878-880.
2. Campbell M. M., Craig R. C., Boyd A. C., Gilbert I. M., Logan R. T., Redpath J., Roy R. G., Savage D. S. and Sleigh T. (1979), Aminosteroids. Part 6. Stereospecific syntheses of eight isomeric, steroidal vicinal 2,3-aminoalcohols. J.Chem.Soc.Perkin Trans. I, 2235-2247.
3. Elenkov I., Todorova D., Bankova V. and Milkova Ts. (1995), Synthesis of steryl esters of phenolic acids by heterogeneous Wittig reaction. J.Nat.Prod. 58, 280-283.
4. Galabov A., Nikolaeva L., Todorova D. and Milkova Ts. (1998), Antiviral activity of cholesteryl esters of cinnamic acid derivatives. Z. Naturforsch. 53c, 883-887.
5. Haworth R., Lunts L. and McKenna J. (1955), The constitution of conessine. Part VIII. Reaction of cholesteryl toluene-p-sulphonate with liquid ammonia. J. Chem. Soc., 986-991.
6. Hewett C. L. and Savage D. S. (1968), Aminosteroids Part III. '2 and 3-amino-5α-androstanes. J. Chem. Soc. C, 1134-1140.
7. Ivanova A., Milkova Ts., Galabov A., Nikolaeva L. and Voynova E. (1997), Transformation of cholanic acid derivatives into pharmacologically active esters of phenolic acids by heterogeneous Wittig reaction. Z. Naturforsch., 516-521.
8. Kalichin Zh., Boneva M., Milkova Ts. and Todorova D. (1997), Study on antioxidant activity of cholesteryl esters of some phenolic acids by chemiluminescence. J.Photochem. Photobiol. 41, 109-113.
9. Koenig W. and Geiger R. (1970), Einc neue Methode zur Synthese von Peptiden. Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxybenzotriazolen. Chem. Berichte 103, 788-798.
10. Kong F. and Anderson R. (1993), Polymastiamide A, a novel steroid (amino acid conjugate isolated from the Norwegian marine sponge Polymastia boletiformis (Lamarck, 1815). J. Org. Chem. 58, 6924-6927.
11. Mokotoff M., Zhao Ming, Marshall R., Winslow E., Wong Lan and Liao Qing-Jiang (1990), Peptidyl aminosteroids as potential new antiarrhythmic agents. Steroids, 399-440.
12. Norris J. R. and Ribbons D. W. (eds.) (1972a), Methods in Microbiology, Vol.7B. Academic Press, London and New York, pp. 216-218.
13. Norris J. R. and Ribbons D. W. (eds.) (1972b), Methods in Microbiology, Vol. 7B. Academic Press, London and New York, pp. 224-233.
14. Overbeek G. A. and Bonta I. L. (1964), Steroid that act on the nervous system. Hormonal Steroids 1, 493-500.
15. Patel K. R., Li M. P., Schuh. J. R. and Baldeschwieler J. D. (1985), Modification of vesicle surfaces with amphiphilic sterols. Effect on permeability and in vivo tissue distribution. Biochim.Biophys. Acta 814, 256-264.
16. Pinkus J., Pinkus G. and Cohen T. (1962), A convenient stereospecific synthesis of axial amines in some steroidal, decalyl and cyclohexyl systems. J. Org. Chem. 27, 4356-4360.
17. Waid T. and Taurins A. (1960), Steroids. Part III. Reduction of oximinocholanic acids. Can. J. Chem. 38, 987-992.