Synthesis of trans-dihydrodiol derivatives of phenanthro[3,4-b]-thiophene and phenanthro[4,3-b]thiophene

Journal of Heterocyclic Chemistry

Volumn 42, Issue 7, 2005, Pages 1345-1355

  Kumar, Subodh ^a   Saravanan, Srinivasan ^a   Reuben, Peter ^a   Kumar, Atul ^a  

^a BUFFALO STATE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6,7 DIHYDROXY 6,7 DIHYDROPHENANTHRO[3,4 B]THIOPHENE; 6,7 DIHYDROXY 6,7 DIHYDROPHENANTHRO[4,3 B]THIOPHENE; 8,9 DIHYDROXY 8,9 DIHYDROPHENANTHRO[3,4 B]THIOPHENE; 8,9 DIHYDROXY 8,9 DIHYDROPHENANTHRO[4,3 B]THIOPHENE; HETEROCYCLIC COMPOUND; PHENANTHRO[3,4 B]THIOPHENE DERIVATIVE; PHENANTHRO[4,3 B]THIOPHENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL CARCINOGENESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; METABOLITE; MUTAGENICITY; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 28244481856     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570420714     Document Type: Conference Paper

References (44)

1. M. L. Lee, M. V. Novotny, and K. D. Bartle, Analytical Chemistry of Polycyclic Aromatic Compounds. Academic Press, New York, 1981
2. M. E. Snook, R. F. Severson, H. C. Higman, R. F. Arrendale, and O. T Chortyk,. in Polynuclear Aromatic Hydrocarbons, P.W. Jones and P. Leber, eds, Ann Arbor Science Publishers Inc, Ann Arbor, Michigan, 1979, pp 231-260.
3. J. Jacob, Sulfur analogues of PAHs (Thiaarenes). Cambridge University Press, Cambridge, 1990, and references therein.
4. J. Schneyder, Faschliche Mitt. Osterr. Tobakregie, 26 (1957).
5. J. Chouteau and M. B. Peyrissac, Ann Inst. Exptl. Tobac. Bergerac., 3, 789 (1961).
6. A. D. Horton and M. R. Guerin, J. Chromatography, 90, 63 (1974).
7. E. R. Schmid, G. Bachlechner, K. Varmuza and H. Klus, Fresenius Z. Anal. Chem., 322, 213 (1985).
8. S. V. Bhide, U. S. Murdial, J. Nair, Cancer Lett., 24, 89 (1984).
9. P. J. Groenen and I. J. van Gemert, J. Chromatography, 57, 239 (1971).
10. G. Becker, A. Colmsjo and C. Ostman, Environ. Sci. Technol., 33, 1321 (1999).
11. M. Ogata, Y. Miyake, K. Fujisawa, S. Kira and Y. Yoshida, Butt. Environ. Contam. Toxicol, 25, 130 (1980).
12. th International Symposium, M. Cooks, A. J. Dennis and G. L. Fisher, eds, Battelle Press. Columbus, Ohio, 1982, pp 845-7
13. A. Croisy, J. Mispelter, J. M. Lhoste, F. Zajdela and P. Jacqignon, J. Heterocyclic Chem., 21, 353 (1984).
14. B. D. Tilak, Tetrahedron, 9, 76 (1960).
15. E. Sinsheimer,; B. H. Hooberman.S. K. Das, P. M. Savla A. J. Ashe III, Environ. Mol. Mutagen., 19, 259 (1992).
16. R. A. Pelroy, D. L. Steward, Y. Tominaga, M. Iwao, R. N. Castle and M. L. Lee, Mutation Res., 117, 31 (1983).
17. The prototype of a bay-region is the hindered region between C10 and C11 of benzo[a]pyrene. The fjord-region is defined as a sterically hindered region in PAHs as exemplified by the region enclosed between positions 1 and 12 of benzo[c]phenanthrene. The K-region is defined as the double bond, typified by the 4,5-bond of benzo[a]pyrene or 5,6-bond of benzo[c]phenanthrene, which is formed by angular fusion of two aromatic rings on a benzene ring.
18. R. E. Lehr, S. Kumar, W. Levin, A. W. Wood, R. L. Chang, A. H. Conney, H. Yagi, J. M. Sayer and D. M. Jerina, In Polycyclic Aromatic Hydrocarbons and Carcinogenesis, ACS symposium series 283, R. G. Harvey, ed. ACS, Washington, D. C., 1985, pp 63-84.
19. R. G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, U.K., 1990.
20. B. Misra and S. Amin, Chem. Res. Toxicol., 3, 93 (1990).
21. S. Kumar, J. Chem. Soc. Perkin Trans. 1, 1018 (2001).
22. S. E. Murphy, S. Amin, K. Coletta and D. Hoffmann, Chem. Res. Toxicol. 5, 491 (1992).
23. Z.-X. Yuan, H. C. Sikka, S. Munir, A. Kumar, A. V. Muruganandam and S. Kumar, Chem Res. Toxicol. 16, 1581 (2003).
24. S. Kumar, J.-M. Lin, J. Whysner, H. C. Sikka and S. Amin, Muation. Res. 545, 11 (2004).
25. A. W. Wood, R. L. Chang, W. Levin, D. E. Ryan, P. E. Thomas, M. Croisy-Delcey, Y Ittah, H. Yagi, D. M. Jerina and A. H. Conney, Cancer Res. 40, 2876 (1980).
26. A. W. Wood, R. L. Chang, W. Levin, D. E. Ryan, P E. Thomas, H. D. Mah, J. M. Karle, H. Yagi, D. M. Jerina and A. H. Conney, Cancer ACT, 39, 4069 (1979).
27. M. Iwao, M. L. Lee, and R. N. Castle, J. Het. Chem. 17, 1259 (1980).
28. B. Misra and S. Amin, J. Org. Chem., 55, 4478 (1990).
29. J. Krzeminski, J.-M. Lin, S. Amin and S. S. Hecht, Chem. Res. Toxicol., 7, 125 (1994).
30. A. S. Kiselyov, H. Lee and R. G. Harvey, J. Org. Chem. 60, 6123 (1995).
31. N. Miyayura and A. Suzuki, Chem. Rev., 95, 2457 (1995).
32. S. Kumar and T. Y. Kim, J. Org. Chem., 65, 3883 (2000).
33. S. Kumar, J. Org. Chem., 67, 8842 (2002).
34. S. Kumar, J. Org. Chem., 62, 8535 (1997).
35. T. T. Upadhya, S. Gurunath and A. Sudalai, Tetrahedron: Asymmetry, 10, 2899 (1999).
36. K. L. Platt, and F. Oesch, Synthesis, 459 (1982).
37. R. S. Bodine, M. Hylarides, G. H. Daub, and D. L. VanderJagt, J. Org. Chem., 43, 4025 (1978).
38. W. E. Bachmann and R. B. Ness, J. Am. Chem. Soc., 64, 536 (1942).
39. W. Baker, J. F. W. McOmie and T.L.V. Ulbricht, J. Chem. Soc., 1825 (1952).
40. J. Cheng, F. Wang; J.-H. Xu,; Y. Pan and Z. Zhang, Tetrahedron Lett., 44, 7095 (2003).
41. A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc., 122, 4020 (2000).
42. T. R. Kasturi and T. Arunachalam, Can. J. Chem., 46, 3625 (1968).
43. K. Rabindran and B. D. Tilak, Curr. Sci., 8, 205 (1951).
44. J. Szmuszkovicz and E. J. Modes, J. Am. Chem. Soc., 72, 571 (1950).