SYNTHESIS OF α-HYDROXYTAMOXIFEN AND ITS 4-HYDROXY ANALOG

REFERENCES

• Powles , T. J. 1997 . Semin. Oncol. , 24 : 1 (b) D. A. Tonetti, V. C. Jordan, Molec. Med. Today 218 (1996).
   PubMed Web of Science ®Google Scholar
• Brown , P. H. and Lippman , S. M. 2000 . Breast Cancer Res. Treat. , 62 : 1 (b) B. Fisher, J. P. Costantino, C. K. Redmond, E. R. Fisher, D. L. Wickerham and W. M. Cronin, J. Natl. Cancer Inst. 86 527 (1994).
   PubMed Web of Science ®Google Scholar
• Curtis , R. E. , Boice , J. D. Jr. , Shriner , D. A. , Hankey , B. F. and Fraumeni , J. F. Jr. 1996 . J. Natl. Cancer Inst. , 88 : 832 (b) R. E. Cuenca, J. Giachino, M. A. Arrendondo, R. Hempling and S. B. Edge, Cancer 77 2058 (1996).
   PubMed Web of Science ®Google Scholar
• Brown , K. , Heydon , R. T. , Jukes , R. , White , I. N. H. and Martin , E. A. 1999 . Carcinogenesis , 20 : 2011 (b) P. Greaves, R. Goonetilleke, G. Nunn, J. Topham and T. Orton, Cancer Res. 53 3919 (1993).
   PubMed Web of Science ®Google Scholar
• Phillips , D. H. 2001 . Carcinogenesis , 22 : 839
   PubMed Web of Science ®Google Scholar
• Kitagawa , M. , Ravindernath , A. , Suzuki , N. , Rieger , R. , Terashima , I. , Umemoto , A. and Shibutani , S. 2000 . Chem. Res. Toxicol. , 13 : 761 (b) E. A. Martin, R. T. Heydon, K. Brown, J. E. Brown, C. K. Lim, I. N. H. White and L. L. Smith, Carcinogenesis 19 1061 (1998). (c) M. R. Osborne, A. Hewer, I. R. Hardcastle, P. L. Carmichael and D. H. Phillips, Cancer Res. 56 66 (1996). (d) D. H. Phillips, P. L. Carmichael, A. Hewer, K. J. Cole, G. K. Poon, Cancer Res. 54 5518 (1994).
   PubMed Web of Science ®Google Scholar
• Shibutani , S. , Ravindernath , A. , Suzuki , N. , Terashima , I. , Sugarman , S. M. , Grollman , A. P. and Pearl , M. L. 2000 . Carcinogenesis , 21 : 1461 (b) S. Shibutani, N. Suzuki, I. Terashima, S. M. Sugarman, A. P. Grollman and M. L. Pearl, Chem. Res. Toxicol. 12 646 (1999).
   PubMed Web of Science ®Google Scholar
• Davis , W. , Venitt , S. and Phillips , D. H. 1998 . Carcinogenesis , 19 : 861 (b) S. Shibutani and L. Dasaradhi, Biochemistry 36 13010 (1997).
   PubMed Web of Science ®Google Scholar
• Hardcastle , I. R. , Horton , M. N. , Osborne , M. R. , Hewer , A. , Jarman , M. and Phillips , D. H. 1998 . Chem. Res. Toxicol. , 11 : 369
   PubMed Web of Science ®Google Scholar
• Osborne , M. R. , Davis , W. , Hewer , A. J. , Hardcastle , I. R. and Phillips , D. H. 1999 . Chem. Res. Toxicol. , 12 : 151 (b) F. A. Beland, L. P. McDaniel and M. M. Marques, Carcinogenesis 20 471 (1999).
   PubMed Web of Science ®Google Scholar
• Foster , A. B. , Jarman , M. , Leung , O.-T. , McCague , R. , Leclercq , G. and Devleeshouwer , N. 1985 . J. Med. Chem. , 28 : 1491
   PubMed Web of Science ®Google Scholar
• Longfellow , C. F. and Jackson , A. O. 1948 . Chem Abstr. , 42 : 1029 USPN 2,429,556
   Google Scholar
• Osborne , C. K. , Coronado , E. , Allred , D. C. , Weibe , V. and DeGregorio , M. J. 1991 . J. Nat. Cancer Inst. , 83 : 1477
   PubMed Web of Science ®Google Scholar
• Shibutani , S. , Dasaradhi , L. , Terashima , I. , Banoglu , E. and Duffel , M. W. 1998 . Cancer Res. , 58 : 647
   PubMed Web of Science ®Google Scholar
• Bedford , G. R. , Walpole , A. L. and Wright , B. 1974 . J. Med. Chem. , 17 : 1
   PubMed Web of Science ®Google Scholar
• Lashley , M. R. , Niedzinski , E. J. , Rogers , J. M. , Denison , M. S. and Nantz , M. H. 2002 . Bioorganic & Med. Chem. , 10 : 4075
   PubMed Web of Science ®Google Scholar
• Xiao , Z. and Timberlake , J. W. 1998 . Tetrahedron , 54 : 4211 (b) P. R. Carlier, K. M. Lo, M. M.-C. Lo, P. C.-K. Lo and C. W.-S. Lo, J. Org. Chem. 62 6316 (1997). (c) J. J. P. Zhou, B. Zhong and R. B. Silverman, J. Org. Chem. 60 2261 (1995). (d) P. R. Carlier and K. M. Lo, J. Org. Chem. 59 4053 (1994).
   Web of Science ®Google Scholar
• The imines derived from 8 and 9 display diastereomeric methyl singlet signals in their 1H NMR spectra (300 MHz, CDCl3) at δ 2.01, 1.97 and δ 1.99, 1.98, respectively
   Google Scholar
• Luche , J.-L. 1978 . J. Am. Chem. Soc. , 100 : 2226
   Web of Science ®Google Scholar
• Michael acceptors 5b, 6a and 6b appear to be somewhat sensitive to storage at room temperature and are known to equilibrate upon exposure to light. Several attempts to obtain elemental analyses always gave combustion data that were slightly off the acceptable tolerance of 0.30
   Google Scholar