Synthesis of 17-oxoandrosta-3,5-dien-3-methyl sulfonate as stable analog of dehydroepiandrosterone sulfate

Steroids

Volumn 63, Issue 4, 1998, Pages 214-217

  Chu, Guo Hua ^a   Jagannathan, Sharada ^a   Li, Pui Kai ^a  

^a DUQUESNE UNIVERSITY   (United States)

Author keywords

Dehydroepiandrosterone sulfate; Memory enhancement; Steroid sulfatase

Indexed keywords

17 OXOANDROSTA 3,5 DIEN 3 METHYL SULFONATE; DRUG ANALOG; NEUROSTEROID; PRASTERONE; PRASTERONE SULFATE; STERYL SULFATASE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG MECHANISM; DRUG SYNTHESIS; MASS SPECTROMETRY; MEMORY; NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

ANDROSTENEDIONE; DEHYDROEPIANDROSTERONE SULFATE; MAGNETIC RESONANCE SPECTROSCOPY; MEMORY; MODELS, CHEMICAL;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032055392     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00006-3     Document Type: Article

References (13)

1. 1. Flood JF, Morley JE, Robert E (1992). Memory-enhancement effects in male mice of pregnenolone and steroids metabolically derived from it. Proc Natl Acad Sci USA 89:1567-1571.
2. 2. Flood JF, Robert E (1988). Dehydroepiandrosterone sulfate improves memory in aging mice. Brain Res 448:178-181.
3. A receptor. Mechanism of action and physiological significance. Prog Neurobiol 38:379-395.
4. 4. Mellon SH (1994). Neurosteroids: biochemistry, modes of action and clinical relevance. J Clin Endocrinol Metab 78:1003-1008.
5. 5. Li PK, Rhodes ME, Jagannathan S and Johnson DA (1995). Reversal of scopolamine induced amnesia in rats by the steroid sulfatase inhibitor estrone-3-O-sulfamate. Cognit Brain Res 2:251-254.
6. 6. Li PK, Rhodes ME, Burke AM and Johnson DA (1997). Memory enhancement mediated by the steroid sulfatase inhibitor (p-O-sulfamoyl)-N-tetradecanoyl tyramine. Life Sci 60:45-51.
7. 7. Chu GH, Li PK (1997). Synthesis of sodium androst-5-ene-17-one-3β-methylene sulfonate. Steroids 62:543-545.
8. 8. Williams JR and Boehm J (1995). The synthesis and reactivity of 3β-(2-alkynylsulfonyl)-and 3β-(2-alkynylsulfonylmethyl) androst-5-en-17-ones as inhibitors of glucose-6-phosphate dehydrogenase. Steroids 60:699-708.
9. 9. Snoody AO (1963). 4-Hydroxy-1-butanesulfonic acid sultone. Org Synth Collect Vol. IV:529-531.
10. 10. Holt DA, Levy MA, Ladd DL, Oh H, Erb JM, Heaslip JI, Brandt M, Metcalf BW (1990). Inhibition of steroid 5-alpha reductase by unsaturated 3-carboxysteroids. J Med Chem 33:937-942.
11. 11. Cacchi S, Morera E, Ortar G (1985). Palladium-catalyzed carbonylation of enol triflates. A novel method for one-carbon homologation of ketones to α,β-unsaturated carboxylic acid derivatives. Tetrahedron Lett. 26:1109-1112.
12. 12. Yadav JS, Mysorekar SV, Sudha V (1989). A facile conversion of tertiary alcohols to olefins. Synth Commun 19:1057-1060.
13. 13. D'Onofrio F, Scettri A (1985). P-toluenesulfonic acid adsorbed on silica gel: An efficient dehydrating agent of alcohols. Synthesis 1159-1161.