D-ring allyl derivatives of 17β- and 17α-estradiols: Chemical synthesis and 13C NMR data

Steroids

Volumn 62, Issue 10, 1997, Pages 674-681

  Dionne, Patricia ^b   Ngatcha, Béatrice Tchédam ^b   Poirier, Donald ^a  

^a LAVAL UNIVERSITY   (Canada)

^b NONE

Author keywords

17 estradiol; 17 estradiol; 13C NMR; Chemical shift; D ring substitution; Magnetic resonance

Indexed keywords

17ALPHA ESTRADIOL; ALLYL COMPOUND; ESTRADIOL; ESTRADIOL DERIVATIVE; ESTRONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ESTROGEN SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; STEREOCHEMISTRY;

ESTRADIOL; ESTRONE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0030806049     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00067-6     Document Type: Article

References (18)

1. von Angerer E (1995). The estrogen receptor as a target for rational drug design. In: Molecular Biology Intelligence Unit. R. G. Landes, Austin, TX, pp. 31-209.
2. Goto G, Yoshioka K, Hiraga K, Miki T (1977). A stereoselective synthesis and nuclear magnetic resonance spectral study of four epimeric 17-hydroxy-16-ethylestranes. Chem Pharm Bull 25:1295-1301.
3. Schneider G, Vass A, Vincze I, Sohar P (1988). Neighbouring group participation in the 16-hydroxymethyl-3-methoxyestra-1,3,5(10)-triene-17β-ol series. Liebigs Ann Chem 267-273.
4. Miyake Y, Kubo Y, Iwabuchi S, Kojima M (1982). Syntheses of 15α- and 15β-carboxymethyltestosterone bovine serum albumin conjugates: Characteristics of the antisera to testosterone. Steroids 40:245-259.
5. 13C nuclear magnetic resonance study of 17α-substituted estradiols. Steroids 60:830-836.
6. Poirier D, Mérand Y, Labrie C, Labrie F (1996). D-ring alkylamide derivatives of estradiol: Effect on ER-binding affinity and antiestrogenic activity. Bioorg Med Chem Lett 6:2537-2542.
7. Bull JR, Loedolff MC (1996). Synthesis of 15,15-dialkylestradiols. J Chem Soc Perkin I 1269-1276.
8. Garrouj ED, Aumelas A, Borgna JL (1993). Steroidal affinity labels of the estrogen receptor. I. 17α-(Bromoacetoxy)alkyl/alkynylestradiols. J Med Chem 36:2973-2983.
9. Sam KM, Auger S, Luu-The V, Poirier D (1995). Steroidal spiro-γ-lactones inhibit 17β-hydroxysteroid dehydrogenase activity in human placental microsomes. J Med Chem 38:4518-4528.
10. Fevig TL, Katzenellenbogen JA (1987). A short, stereoselective route to 16α-(substituted-alkyl) estradiol derivatives. J Org Chem 52:247-251.
11. Pelletier JD, Labrie F, Poirier D (1994). N-butyl, N-methyl, 11-(3′,17′β-dihydroxy-1′,3′,5′(10′) estratriene-16′α-yl)-9-bromo undecanamide: Synthesis, 17β-HSD inhibiting activity, estrogenic activity and antiestrogenic activity. Steroids 551:536-547.
12. Tremblay MR, Auger S, Poirier D (1995). Synthesis of 16-(bromoalkyl)-estradiols having inhibitory effect on human placental estradiol 17β-hydroxysteroid dehydrogenase (17β-HSD type 1). Bioorg Med Chem 3:505-523.
13. Sam KM, Boivin RP, Auger S, Poirier D (1994). 16α-Propyl derivatives of estradiol as inhibitors of 17β-hydroxysteroid dehydrogenase type 1. Bioorg Med Chem Lett 4:2129-2132.
14. Goto G, Yoshioka K, Hiraga K, Masuoka M, Nakayama R, Miki T (1978). Synthesis and antiandrogenic activity of 16β-substituted-17β-hydroxysteroids. Chem Pharm Bull 26:1718-1728.
15. Bojack G, Kunzer H (1994). An oxy-cope rearrangement approach to C(15) α-alkylated derivatives of estradiol. Tetrahedron Lett 35: 9025-9026.
16. Trost BM, Parquette JR (1993). Methyl 2-Pyridinesulfinate. A convenient reagent for sulfinylation-dehydrosulfinylation. J Org Chem 58:1579-1581.
17. Dodge JA, Lugar III CW (1996). Alcohol inversion of 17β-steroids. Bioorg Med Chem Lett 6:1-2.
18. 13C NMR spectra of steroids, a survey and commentary. Org Magn Res 9:439-464.