Regioselective Bromination of a Thymine–Acridine Conjugate by N-Bromosuccinimide

REFERENCES

• Podgorsek , A. ; Stavber , S. ; Zupan , M. ; Iskra , J. Visible light induced “on water” benzylic bromination with N-bromosuccinimide . Tetrahedron Lett. 2006 , 47 , 1097 – 1099 .
   Google Scholar
• Djerassi , C. Brominations with N-bromosuccinimide and related compounds: The Wohl–Ziegler reaction . Chem. Rev. 1948 , 43 , 271 – 317 .
   PubMed Web of Science ®Google Scholar
• Al Hariri , M. ; Galley , O. ; Pautet , F. ; Fillion , H. Selective bromination of 4,5-dimethylthiazole with N-bromosuccinimide . Eur. J. Org. Chem. 1998 , 4 , 593 – 594 .
   Google Scholar
• Bovonsombat , P. ; McNelis , E. Ring halogenations of polyalkylbenzenes with N-halosuccinimide and acidic catalysts . Synthesis 1993 , 237 – 241 .
   Google Scholar
• Pizey , J. S. Synthetic Reagents ; Wiley & Sons : New York , 1974 .
   Google Scholar
• Kim , K. N. ; Lee , J. ; Kim , D. H. ; Yoo , J.-S. ; Kwon , H. J. A new synthetic analogue of thymidine, 7-(3-bromo-phenoxy)-thymidine, inhibits the proliferation of tumor cells . Bioorg. Med. Chem. Lett. 2005 , 15 , 77 – 79 .
   PubMedGoogle Scholar
• Grover , R. K. ; Pond , S. J. K. ; Cui , Q. ; Subramaniam , P. ; Case , D. A. ; Millar , D. P. ; Wentworth , P. J. O-Glycoside orientation is an essential aspect of base J recognition by the kinetoplastid DNA-binding protein JBP1. Angew. Chem. Int. Ed. 2007, 46, 2839–2843.
   PubMedGoogle Scholar
• Binkley , R. W. ; Goewey , G. S. ; Johnston , J. C. Regioselective ring opening of selected benzylidene acetals: A photochemically initiated reaction for partial deprotection of carbohydrates . J. Org. Chem. 1984 , 49 , 992 – 996 .
   Google Scholar
• Sugaya , T. ; Mimura , Y. ; Shida , Y. ; Osawa , Y. ; Matsukuma , I. ; Ikeda , S. ; Akinaga , S. ; Morimoto , M. ; Ashizawa , T. ; Okabe , M. ; Ohno , H. ; Gomi , K. ; Kasai , M. 6H-Pyrazolo[4,5,1-de]acridin-6-ones as a novel class of antitumor agents: Synthesis; and biological activity . J. Med. Chem. 1994 , 37 , 1028 – 1032 .
   PubMed Web of Science ®Google Scholar
• Amat , M. ; Hadida , A. M. ; Sathyanarayana , S. ; Bosch , J. Regioselective synthesis of 3-substituted indoles: 3-Ethylindole . Org. Synth. 1997 , 74 , 248 – 256 .
   Google Scholar
• Schmid , H. ; Leutenegger , W. E. The action of N-bromosuccinimide on acridine, III . Helv. Chim. Acta 1947 , 30 , 1965 – 1975 .
   PubMedGoogle Scholar
• Gruter , G.-J. M. ; Akkerman , O. S. ; Bickelhaupt , F. Nuclear versus side-chain bromination of methyl-substituted anisoles by N-bromosuccinimide . J. Org. Chem. 1994 , 59 , 4473 – 4481 .
   Web of Science ®Google Scholar
• Mitchell , R. H. ; Lai , Y. H. ; Williams , R. V. N-Bromosuccinimide–dimethylformamide: A mild, selective nuclear monobromination reagent for reactive aromatic compounds . J. Org. Chem. 1979 , 44 , 4733 – 4735 .
   Web of Science ®Google Scholar
• Goldberg , Y. ; Bensimon , C. ; Alper , H. Highly regioselective bromination of 2,3-dimethylanisole with N-bromosuccinimide . J. Org. Chem. 1992 , 57 , 6374 – 6376 .
   Google Scholar
• Berube , G. ; Rabouin , D. ; Perron , V. ; N'Zemba , B. ; Gaudreault , R.-C. ; Parent , S. ; Asselin , E. Synthesis of unique 17-β-estradiol homo-dimers, estrogen receptors' binding affinity evaluation and cytocidal activity on breast, intestinal, and skin cancer cell lines . Steroids 2006 , 71 , 911 – 921 .
   PubMedGoogle Scholar