Stereochemistry of 1,5-benzothiazepin-4-one S-oxide: Insight into the stereogenic elements at the sulfur atom and axis

Journal of Organic Chemistry

Volumn 78, Issue 12, 2013, Pages 6264-6270

  Tabata, Hidetsugu ^a   Yoneda, Tetsuya ^a   Oshitari, Tetsuta ^a   Takahashi, Hideyo ^a   Natsugari, Hideaki ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY;

DIASTEREOMERS; EQUILIBRIUM RATIOS; INTERCONVERSIONS; S OXIDES; STEREOGENIC AXIS; SULFUR ATOMS;

ORGANIC COMPOUNDS;

1,5 BENZOTHIAZEPIN 4 ONE SULFOXIDE; BENZOTHIAZEPINE DERIVATIVE; SULFONE; SULFOXIDE; SULFUR OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; OXIDATION; STEREOCHEMISTRY;

EID: 84879367869     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401020y     Document Type: Article

References (35)

1. Kugita, H.; Inoue, H.; Ikezaki, M.; Konda, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595-602
2. Bariwal, J. B.; Upadhyay, K. D.; Manvar, A. T.; Trivedi, J. C.; Singh, J. S.; Jain, K. S.; Shah, A. K. Eur. J. Med. Chem. 2008, 43, 2279-2290
3. Krapcho, J.; Spitzmiller, E. R.; Turk, C. F. J. Med. Chem. 1963, 6, 544-546
4. Krapcho, J.; Turk, C. F. J. Med. Chem. 1966, 9, 191-195
5. Krapcho, J.; Turk, C. F.; Piala, J. J. J. Med. Chem. 1968, 11, 361-364
6. DeVita, R. J.; Schoen, W. R.; Doldouras, G. A.; Fisher, M. H.; Wyvratt, M. J.; Cheng, K.; Chan, W. W.-S.; Butler, B. S.; Smith, R. G. Bioorg. Med. Chem. Lett. 1995, 5, 1281-1286
7. Slade, J.; Stanton, J. L.; Ben-David, D.; Mazzenga, G. C. J. Med. Chem. 1985, 28, 1517-1521
8. Itoh, K.; Kori, M.; Inada, Y.; Nishikawa, K.; Kawamatsu, Y.; Sugihara, H. Chem. Pharm. Bull. 1986, 34, 1128-1147
9. Skiles, J. W.; Sorcek, R.; Jacober, S.; Miao, C.; Mui, P. W.; McNeil, D.; Rosenthal, A. S. Bioorg. Med. Chem. Lett. 1993, 3, 773-778
10. Campiani, G.; Nacci, V.; Fiorini, I.; De Filippis, M. P.; Garofalo, A.; Greco, G.; Novellino, E.; Altamura, S.; Di Renzo, L. J. Med. Chem. 1996, 39, 2672-2680
11. Natsugari, H.; Ikeura, Y.; Kamo, I.; Ishimaru, T.; Ishichi, Y.; Fujishima, A.; Tanaka, T.; Kasahara, F.; Kawada, M.; Doi, T. J. Med. Chem. 1999, 42, 3982-3993
12. Albert, J. S.; Aharony, D.; Andisik, D.; Barthlow, H.; Bernstein, P. R.; Bialecki, R. A.; Dedinas, R.; Dembofsky, B. T.; Hill, D.; Kirkland, K.; Koether, G. M.; Kosmider, B. J.; Ohnmacht, C.; Palmer, W.; Potts, W.; Rumsey, W.; Shen, L.; Shenvi, A.; Sherwood, S.; Warwick, P. J.; Russell, K. J. Med. Chem. 2002, 45, 3972-3983
13. Clayden, J. Tetrahedron 2004, 60, 4335
14. Guile, S. D.; Bantick, J. R.; Cooper, M. E.; Donald, D. K.; Eyssade, C.; Ingall, A. H.; Lewis, R. J.; Martin, B. P.; Mohammed, R. T.; Potter, T. J.; Reynolds, R. H.; St-Gallay, S. A.; Wright, A. D. J. Med. Chem. 2007, 50, 254-263
15. Lee, S.; Kamide, T.; Tabata, H.; Takahashi, H.; Shiro, M.; Natsugari, H. Bioorg. Med. Chem. 2008, 16, 9519-9523
16. Tabata, H.; Akiba, K.; Lee, S.; Takahashi, H.; Natsugari, H. Org. Lett. 2008, 10, 4871-4874
17. Porter, J.; Payne, A.; Whitcombe, I.; de Candole, B.; Ford, D.; Garlish, R.; Hold, A.; Hutchinson, B.; Trevitt, G.; Turner, J.; Edwards, C.; Watkins, C.; Davis, J.; Stubberfield, C. Bioorg. Med. Chem. Lett. 2009, 19, 1767-1772
18. Clayden, J.; Moran, W. J.; Edwards, P. J.; LaPlante, S. R. Angew. Chem., Int. Ed. 2009, 48, 6398-6401
19. LaPlante, S. R.; Edwards, P. J.; Fader, L. D.; Jakalian, A.; Hucke, O. Chem. Med. Chem 2011, 6, 505-513
20. Takahashi, H.; Wakamatsu, S.; Tabata, H.; Oshitari, T.; Harada, A.; Inoue, K.; Natsugari, H. Org. Lett. 2011, 13, 760-763
21. Tabata, H.; Nakagomi, J.; Morizono, D.; Oshitari, T.; Takahashi, H.; Natsugari, H. Angew. Chem., Int. Ed. 2011, 50, 3075-3079
22. Tabata, H.; Wada, N.; Takada, Y.; Oshitari, T.; Takahashi, H.; Natsugari, H. J. Org. Chem. 2011, 76, 5123-5131
23. Tabata, H.; Wada, N.; Takada, Y.; Nakagomi, J.; Miike, T.; Shirahase, H.; Oshitari, T.; Takahashi, H.; Natsugari, H. Chem.-Eur. J. 2012, 18, 1572-1576
24. Breitschuh, R.; Seebach, D. Synthesis 1992, 1170-1178
25. 2 axis at Ar-N(C=O), which exists in the latent form and is moving together like a gear with the stereochemistry specified by the two chiral centers at 1 S and 2 C
26. 1H chemical shifts in NMR for sulfoxides and sulfones in general, see: Abraham, R. J.; Byrne, J. J.; Griffiths, L. Magn. Reson. Chem. 2008, 46, 667-675
27. 3 J) correspond well with those estimated from the torsion angles by the Karplus equation. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870-2871
28. Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48-76
29. Jeffrey, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: Oxford, U.K., 1997.
30. Axelrod, M.; Bickart, P.; Jacobus, J.; Green, M. M.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4835-4842
31. Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K.; Rayner, D. R.; Gordon, A. J.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4854-4860
32. Miller, E. G.; Rayner, D. R.; Thomas, H. T.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4861-4868
33. Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869-4876
34. ⧧ values, see: Petit, M.; Lapierre, A. J. B.; Curran, D. P. J. Am. Chem. Soc. 2005, 127, 14994-14995
35. For an informative study on the correlation of absolute configuration and the chiroptical properties of alkyl aryl sulfoxides, see: Rosini, C.; Donnoli, M. I.; Superchi, S. Chem.-Eur. J, 2001, 7, 72-79