Synthesis and Evaluation of Benzoxazolinonic Imidazoles and Derivatives as Non-steroidal Aromatase Inhibitors

References

• Simpson, E.R., Mahendroo, M.S., Means, G.D., Kilgore, M.W., Hinshelwood, M.M., Graham-Lorence, S., Amarneh, B., Ito, Y., Fisher, C.R., Michael, M.D., et al. (1994) “Aromatase cytochrome P450, the enzyme responsible for estrogen biosynthesis”, Endocr. Rev. 15, 342–355.
   PubMed Web of Science ®Google Scholar
• Bulun, S.E., Mahendroo, M.S. and Simpson, E.R. (1994) “Aromatase gene expression in adipose tissue: relationship to breast cancer”, J. Steroid Biochem. Mol. Biol. 49, 319–326.
   PubMed Web of Science ®Google Scholar
• Lu, Q., Nakmura, J., Savinov, A., Yue, W., Weisz, J., Dabbs, D.J., Wolz, G. and Brodie, A. (1996) “Expression of aromatase protein and messenger ribonucleic acid in tumor epithelial cells and evidence of functional significance of locally produced estrogen in human breast cancers”, Endocrinol. 137, 3061–3068.
   PubMed Web of Science ®Google Scholar
• Bulun, S.E., Rosenthal, I.M., Brodie, A.M., Inkster, S.E., Zeller, W.P., DiGeorge, A.M., Frasier, S.D., Kilgore, M.W. and Simpson, E.R. (1994) “Use of tissue-specific promoters in the regulation of aromatase cytochrome P450 gene expression in human testicular and ovarian sex cord tumors, as well as in normal fetal and adult gonads”, J. Clin. Endocrinol. Metab. 78, 1616–1621.
   PubMed Web of Science ®Google Scholar
• Harada, M., Nemoto, R., Uchida, K., Akaza, H., Koiso, K. and Mostofi, F.K. (1993) “Histopathological comparison of prostatic adenocarcinoma in Japan and the United States”, Nippon Hinyokika Gakkai Zasshi 84, 1110–1118.
   PubMedGoogle Scholar
• Brodie, A.M. (1994) “Aromatase inhibitors in the treatment of breast cancer”, J. Steroid Biochem. Mol. Biol. 49, 281–287.
   PubMed Web of Science ®Google Scholar
• Se´ralini, G.-E. and Moslemi, S. (2001) “Aromatase inhibitors: past, present and future”, Mol. Cell. Endocrinol. 178, 117–131.
   PubMed Web of Science ®Google Scholar
• Santen, R.J. and Misbin, R.I. (1981) “Aminoglutethimide: review of pharmacology and clinical use”, Pharmacotherapy 1, 95–120.
   PubMed Web of Science ®Google Scholar
• Marsh, D.A., Brodie, H.J., Garrett, W., Tsai-Morris, C.H. and Brodie, A.M. (1985) “Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives”, J. Med. Chem. 28, 788–795.
   PubMed Web of Science ®Google Scholar
• Brodie, A.M., Garrett, W.M., Hendrickson, J.R., Tsai-Morris, C.H., Marcotte, P.A. and Robinson, C.H. (1981) “Inactivation of aromatase in vitro by 4-hydroxy-4-androstene-3,17-dione and 4-acetoxy-4-androstene-3,17-dione and sustained effects in vivo”, Steroids 38, 693–702.
   PubMed Web of Science ®Google Scholar
• Lonning, P.E. (1996) “Aromatase inhibition for breast cancer treatment”, Acta Oncol. 35(Suppl. 5), 38–43.
   Google Scholar
• Auvray, P., Sourdaine, P., Moslemi, S., Seralini, G.E., Sonnet, P., Enguehard, C., Guillon, J., Dallemagne, P., Bureau, R. and Rault, S. (1999) “MR 20492 and MR 20494: two indolizinone derivatives that strongly inhibit human aromatase”, J. Steroid Biochem. Mol. Biol. 70, 59–71.
   PubMed Web of Science ®Google Scholar
• Sonnet, P., Dallemagne, P., Guillon, J., Enguehard, C., Stiebing, S., Tanguy, J., Bureau, R., Rault, S., Auvray, P., Moslemi, S., Sourdaine, P. and Seralini, G.-E. (2000) “New aromatase inhibitors. Synthesis and biological activity of aryl- substituted pyrrolizine and indolizine derivatives”, Bioorg. Med. Chem. 8, 945–955.
   PubMed Web of Science ®Google Scholar
• Graham-Lorence, S., Amarneh, B., White, R.E., Peterson, J.A. and Simpson, E.R. (1995) “A three-dimensional model of aromatase cytochrome P450”, Protein Sci. 4, 1065–1080.
   PubMed Web of Science ®Google Scholar
• Gaillard, J.L. and Silberzahn, P. (1987) “Aromatization of 19-norandrogens by equine testicular microsomes”, J. Biol. Chem. 262, 5717–5722.
   PubMed Web of Science ®Google Scholar
• Moslemi, S. and Seralini, G.-E. (1997) “Inhibition and inactivation of equine aromatase by steroidal and non- steroidal compounds. A comparison with human aromatase inhibition”, J. Enz. Inhib. 12, 241–254.
   Google Scholar
• Se´ralini, G.-E., Tomilin, A., Auvray, P., Nativelle-Serpentini, C., Souradaine, P. and Moslemi, S. (2003) “Molecular characterization and expression of equine testicular cyto- chrome P450 aromatase”, Biochem. Biophys. Acta Gene Struct. Expr. 1625, 229–238.
   PubMed Web of Science ®Google Scholar
• Auvray, P., Moslemi, S., Sourdiane, P., Galopin, S., Seralini, G.E., Sonnet, P., Guillon, J., Enguehard, C., Dallemagne, P., Bureau, R. and Rault, S. (1998) “Design and synthesis of a new type of non steroidal human aromatase inhibitors”, Bioorg. Med. Chem. Lett. 8, 1041–1044.
   PubMed Web of Science ®Google Scholar
• Le Borgne, M., Marchand, P., Delevoye-Seiller, B., Robert, J.M., Le Baut, G., Hartmann, R.W. and Palzer, M. (1999) “New selective nonsteroidal aromatase inhibitors: synthesis and inhibitory activity of 2,3 or 5-(alpha-azolylbenzyl)-1H- indoles”, Bioorg. Med. Chem. Lett. 9, 333–336.
   PubMed Web of Science ®Google Scholar
• Marchand, P., Le Borgne, M., Palzer, M., Le Baut, G. and Hartmann, R.W. (2003) “Preparation and pharmacological profile of 7-(alpha-Azolylbenzyl)-1H-indoles and indolines as new aromatase inhibitors”, Bioorg. Med. Chem. Lett. 13, 1553–1555.
   PubMed Web of Science ®Google Scholar
• A¨ıchaoui, H., Poupaert, J.H., Lesieur, D. and He´nichart, J.P. (1991) “Regioselectivity in the C-acylation of 2(3H)-benzox- azolones”, Tetrahedron 47, 6649–6654.
   Web of Science ®Google Scholar
• A¨ıchaoui, H., Lesieur, D. and He´ nichart, J.P. (1992) “A convenient and efficient method for the preparation of 6-Acyl-2(3H)-benzoxazolones”, J. Heterocyclic Chem. 29, 171–175.
   Google Scholar
• Moussavi, Z., Lesieur, D., Lespagnol, C., Sauziere, J. and Olivier, P. (1989) “Acyl-7 dihydro-2,3 benzoxazin-1,4 ones-3 et proprietes normolipemiantes”, Eur. J. Med. Chem. Chim. Ther. 24, 55–60.
   Web of Science ®Google Scholar
• Moussavi, Z., Depreux, P., Lesieur, I. and Sauziere, J. (1991) “Synthesis of conformationally restrained analogs of 7-n-butyryl-2,3-dihydro-3-oxo(1,4)-benzoxazinone a nor- molipemic pharmacophoric pattern”, Heterocycles 32, 2119–2125.
   Web of Science ®Google Scholar
• Yous, S., Poupaert, J.H., Lesieur, I., Depreux, P. and Lesieur, D. (1994) “AlCl3-DMF reagent in the Friedel-Crafts reaction. Application to the acylation reaction of 2(3H)-benzothiazo- lone”, J. Org. Chem. 59, 1574–1576.
   Web of Science ®Google Scholar
• Dintinger, T., Gaillard, J.L., Moslemi, S., Zwain, I. and Silberzahn, P. (1989) “Androgen and 19-norandrogen aroma- tization by equine and human placental microsomes”, J. Steroid Biochem. 33, 949–954.
   PubMedGoogle Scholar
• Bradford, M.M. (1976) “A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding”, Anal. Biochem. 72, 248– 254.
   PubMed Web of Science ®Google Scholar
• Thompson, E.A., Jr. and Siiteri, P.K. (1974) “The involvement of human placental microsomal cytochrome P-450 in aromatization”, J. Biol. Chem. 249, 5373–5378.
   PubMed Web of Science ®Google Scholar
• Mosmann, T. (1983) “Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays”, J. Immunol. Meth. 65, 55–63.
   PubMed Web of Science ®Google Scholar
• Brodie, A.M. and Longcope, C. (1980) “Inhibition of peripheral aromatization by aromatase inhibitors, 4-hydroxy- and 4-acetoxy-androstene-3,17-dione”, Endocrinol. 106, 19–21.
   PubMed Web of Science ®Google Scholar
• Santen, R.J., Langecker, P., Santner, S.J., Sikka, S., Rajfer, J. and Swerdloff, R. (1990) “Potency and specificity of CGS-16949A as an aromatase inhibitor”, Endocr. Res. 16, 77–91.
   PubMed Web of Science ®Google Scholar
• Peterson, J.A. and Griffin, B.W. (1972) “Carbon monoxide binding by Pseudomonas putida cytochrome P-450”, Arch. Biochem. Biophys. 151, 427–433.
   PubMed Web of Science ®Google Scholar
• Covey, D.F. and Hood, W.F. (1982) “A new hypothesis based on suicide substrate inhibitor studies for the mechanism of action of aromatase”, Cancer Res. 42(8 Suppl.), 3327s-3333s.
   Google Scholar
• Schenkman, J.B. (1970) “Studies on the nature of the type I and type II spectral changes in liver microsomes”, Bio- chemistry 9, 2081–2091.
   Google Scholar
• Wright, J.L., Slatcher, M. and Akhtar, M. (1991) “‘Slow- binding’ sixth-ligand inhibitors of cytochrome P-450 aromatase. Studies with 19-thiomethyl- and 19-azido- androstenedione”, Biochem. J. 273, 533–539.
   PubMed Web of Science ®Google Scholar
• Hartmann, R.W., Bayer, H., Grun, G., Sergejew, T., Bartz, U. and Mitrenga, M. (1995) “Pyridyl-substituted tetrahydro- cyclopropa(a)naphthalenes: highly active and selective inhibitors of P450arom”, J. Med. Chem. 38, 2103–2111.
   PubMed Web of Science ®Google Scholar