Enantioselective total synthesis and structure determination of the mercapturic acid sulfoxide conjugate

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 15, 1997, Pages 2033-2036

  Nakamura, Shizuo ^a   Goto, Kiyoto ^a   Kondo, Mitsuyoshi ^a   Naito, Shinsaku ^a   Tsuda, Yoshiaki ^a   Shishido, Kozo ^b  

^a OTSUKA PHARMACEUTICAL CO LTD   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; ACETYLCYSTEINE DERIVATIVE; DRUG METABOLITE; NONSTEROID ANTIINFLAMMATORY AGENT;

ARTICLE; CHIRALITY; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030744472     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00363-6     Document Type: Article

References (12)

1. Nakamura, S.; Kondo, M.; Goto, K.; Naito, S.; Tsuda, Y.; Shishido, K. Heterocycles 1995, 41, 1131-1134.
2. Nakamura, S.; Kondo, M.; Goto, K.; Nakamura, M.; Tsuda, Y.; Shishido, K. Heterocycles 1996, 43, 2747-2755.
3. Haber, S. B. U.S. Patent 4590205 (Chem. Abstr. 1984, 100, 22571).
4. Copeland, R. A.; Williams, J. M.; Giannaras, J.; Nurnberg, S.; Covington, M.; Pinto, D.; Pick, S.; Trzaskos, J. M. Proc. Natl. Acad. Sci. USA 1994, 91, 11202-11206.
5. The ratio of the metabolite 4 was determined by measuring the peak areas of the product ion chromatograms at m/z 379 and m/z 331 (precursor ion [M-H]-m/z 508), shown below, employing the LC-MS/MS selected ion monitoring technique. (Formula Presented)
6. -. B/E linked scan of m/z 379, fragment ion; m/z 331.
7. Nakamura, S.; Goto, K.; Kondo, M.; Naito, S.; Bando, M.; Kido, M.; Shishido, K. Bioorg. Med. Chem. Lett. 1996, 6, 937-940.
8. For a review, see: Hughes, D. L. Organic React. 1992, 42, 335-656.
9. Ireland, R. E.; Thompson, W. J. Tetrahedron Lett. 1979, 4705-4708.
10. 3: C, 52.25; H, 4.72; N, 2.34. Found: C, 51.92; H, 4.75; N, 2.26.
11. Corey, E. J.; Gras, J. -L.; Ulrich, P. Tetrahedron Lett. 1976, 809-812.
12. 2O: C, 50.95; H, 4.08; N, 2.71. Found: C, 51.23; H, 4.07; N, 2.73.