Methyl hypofluorite in the synthesis of 16-methoxyestradiol stereoisomers

Steroids

Volumn 63, Issue 9, 1998, Pages 470-478

  Jonson, Stephanie D ^a,b   D'Avignon, D André ^b   Katzenellenbogen, John A ^c   Welch, Michael J ^a,b  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b WASHINGTON UNIVERSITY   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

16 methoxyestradiol; HMQC TOCSY; Methyl hypofiuorite; NOESY

Indexed keywords

16 METHOXYESTRADIOL; ESTRADIOL; ESTRADIOL DERIVATIVE; ESTRIOL; ESTROGEN RECEPTOR; FLUORINE DERIVATIVE; LIGAND; METHYL HYPOFLUORITE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM;

ESTERS; ESTRADIOL; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROTEIN BINDING; RECEPTORS, ESTROGEN; STEREOISOMERISM; TOMOGRAPHY, EMISSION-COMPUTED;

EID: 0031851686     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(98)00051-8     Document Type: Article

References (30)

1. Dehdashti F, Mortimer JE, Siegel BA, Griffeth LK, Dobkin JA, Bonasera TA, Fusselman MJ, Detert DD, Cutler PD, Katzenellenbogen JA, Welch MJ (1995). Positron tomographic assessment of estrogen receptors in breast cancer: comparison with FDG-PET and in vitro receptor assays. J Nucl Med 36:1766-1774.
2. 18F] fluoro-17β-estradiol uptake in metastatic breast carcinoma. J Nucl Med 32:1526-1531.
3. Mintun MA, Welch MJ, Siegel BA, Mathias CJ, Brodack JW, McGuire AH, Katzenellenbogen JA (1988). Breast cancer: PET imaging of estrogen receptors. Radiology 169:45-48.
4. 18F]fluoroestradiols: selective receptor-based PET imaging agents. Nucl Med Biol 19:363-374.
5. 18F]Fluoro)estrogens: systematic investigation of a new series of fluorine-18-labeled estrogens as potential imaging agents for estrogen-receptor-positive breast tumors. J Med Chem 36:1619-1629.
6. 18F]Fluoromoxestrol: a potent, metabolically stable Positron Emission Tomography imaging agent for estrogen receptor positive human breast tumors. Life Sci 53:811-819.
7. VanBrocklin HF, Liu A, Welch MJ, O'Neil JP, Katzenellenbogen JA (1994). The synthesis of 7α-methyl-substituted estrogens labeled with fluorine-18: potential breast tumor imaging agents. Steroids 59:34-45.
8. French AN, Wilson SR, Welch MJ, Katzenellenbogen JA (1993). A synthesis of 7α-substituted estradiols: synthesis and biological evaluation of a 7α-pentyl-substituted BODIPY fluorescent conjugate and a fluorine-18-labeled 7α-pentylestradiol analog. Steroids 58:157-169.
9. French AN, Napolitano E, VanBrocklin HF, Hanson RN, Welch MJ, Katzenellenbogen JA (1993). Synthesis, radiolabeling and tissue distribution of 11β-fluoroalkyl- and 11β-fluoroalkoxy-substituted estrogens: target tisue uptake selectivity and defluorination of a homologous series of fluorine-18-labeled estrogens. Nucl Med Biol 20:31-47.
10. Pomper MG, VanBrocklin HF, Thieme AM, Thomas RD, Kiesewetter DO, Carlson KE, Mathias CJ, Welch MJ, Katzenellenbogen JA (1990). 11β-Methoxy-, 11β-ethyl- and 17α-ethynyl-substituted 16α-fluoroestradiols: receptor-based imaging agents with enhanced uptake efficiency and selectivity. J Med Chem 33:3143-3155.
11. Dence CS, Napolitano E, Katzenellenbogen JA, Welch MJ (1996). Carbon-11 labeled estrogens as potential imaging agents for breast tumors. Nucl Med Biol 23:491-496.
12. Långström BR (1990). Synthesis of novel carbon-11 precursors. Acta Chem Scan 147:8374.
13. 11C labelled methyl hypofluorite. J Chem Soc Chem Commun 6:561-562.
14. 2). J Am Chem Soc 114:7643-7645.
15. Rozen S, Mishani E, Kol M, Ben-David I (1994). The chemistry of methyl hypofluorite: its reactions with various unsaturated centers. J Org Chem 59:4281-4284.
16. Kol M, Rozen S, Appelman E (1991). Isolation and characterization of methyl hypofluorite. J Am Chem Soc 113:2648-2651.
17. Corey EJ, Knapp S (1976). α-Functionalization of ketones via N,N,-dimethylhydrazones. Tetrahedron Lett 51:4687-4690.
18. Moriarty RM, Prakash O, Duncan MP, Vaid RK (1987). Hypervalent iodine oxidation of silyl enol ethers under Lewis acid conditions in methanol. A general route to α-methoxy ketones. J Org Chem 52: 150-153.
19. Katzenellenbogen JA (1996). Estrogen and progestin radiopharmaceuticals for imaging breast cancer. In: Moudgil VK (ed), Estrogens, Progestins, and their Antagonists. Birkhäuser, Boston, pp. 197-242.
20. Fevig T, Mao M, Katzenellenbogen J (1988). Estrogen receptor binding tolerance of 16α-substituted estradiol derivatives. Steroids 51: 471-497.
21. Anstead G, Carlson K, Katzenellenbogen J (1997). The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 62: 268-303.
22. Arunachalam T, Longcope C, Caspi E (1979). Iodoestrogens, syntheses, and interactions with uterine receptors. J Biol Chem 254:5900-5905.
23. Zeng B, Pollack R, Summers M (1990). Conformational analysis via heteronuclear correlation NMR spectroscopy. J Org Chem 55:2534-2536.
24. Braunschweiler L, Ernst RR (1983). Coherence transfer by Isotropic mixing: application to proton correlation spectroscopy. J Mag Res 53:521-528.
25. Vyplel H (1985). Präparative fluorierungen mit molekularem fluor. Chimia 39:305.
26. Kiesewetter DO, Katzenellenbogen JA, Kilbourn MR, Welch MJ (1984). Synthesis of 16-fluoroestrogens by unusually facile fluoride ion displacement reactions: prospects for the preparation of fluorine-18 labeled estrogens. J Org Chem 49:4900-4905.
27. Cazeau P, Duboudin F, Moulines F, Babot O, Dunogues J (1987). A new practical synthesis of silyl enol ethers. Part I. From simple aldehydes and ketones. Tetrahedron 43:2075-2088.
28. Katzenellenbogen JA, Johnson Jr. HJ, Myers HN (1973). Photoaffinity labels for estrogen binding proteins of rat uterus. Biochemistry 12: 4085-4092.
29. Cotton FA, Wilkinson G (1988). Advanced Inorganic Chemistry. John Wiley & Sons, New York, p. 108.
30. Numazawa M, Nagaoka M, Tsuji M (1983). Novel and efficient synthesis of estriol and its 16-glucuronide via 2,4,16α-tribromoestrone. J Chem Soc Perkin Trans 7:121-125.