Structural assignment of stilbenethiols and chalconethiols and differentiation of their isomeric derivatives by means of1H- and 13C-NMR spectroscopy

Spectroscopy Letters

Volumn 38, Issue 4-5, 2005, Pages 477-485

  Nowakowska, Zdzisława ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

13C NMR; 1H NMR; Chalcone; Correlation techniques (COSY, HETCOR); Coupling constant; Stilbene

Indexed keywords

EID: 23044456219     PISSN: 00387010     EISSN: None     Source Type: Journal    
DOI: 10.1081/SL-200062816     Document Type: Article

References (21)

1. Opletalova, V. Chalcones and their heterocyclic analogs as potential therapeutic agents in bacterial diseases. Ceska Slov. Farm. 2000, 49 (6), 278-284.
2. Ballesteros, J. F.; Sanz, M. J.; Ubeda, A.; Miranda, M. A.; Iborra, S.; Paya, M.; Alcaraz, M. J. Synthesis and pharmacological evaluation of 2′-hydroxychalcones and flavones as inhibitors of inflammatory mediators generation. J. Med. Chem. 1995, 38 (14), 2794-2797.
3. Dimmock, J.; Elias, D.; Beazely, M.; Kandepu, N. Bioactivities of chalcones. Curr. Med. Chem. 1999, 6 (12), 1125-1149.
4. Mukherjee, S.; Kumar, V.; Prasad, A.; Raj, H.; Bracke, M.; Olsen, C.; Jain, S.; Parmar, V. Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones. Bioorg. Med. Chem. 2001, 9 (2), 337-345.
5. Yoshikawa, M.; Shimada, H.; Yagi, N.; Murakami, N.; Shimoda, H. Development of bioactive functions in Hydrangeae Dulcis Folium. VI. Syntheses of thunberginols A and F and their 3′-deoxy-derivatives using regiospecific lactonization of stilbene carboxylic acid: structures and inhibitory activity on histamine release. Chem. Pharm. Bull. 1996, 44 (10), 1890-1898.
6. Schultz, T. P.; Cheng, Q.; Boldin, W. D.; Hubbard, T.; F. Jin, L.; Fisher, T. H.; Nicholas, D. D. Comparision of the fungicidal activities of (E)-4-hydroxylated stilbenes and related bibenzyls. Phytochemisiry 1991, 30 (9), 2939-2945.
7. Kikumoto, R.; Tobe, A.; Fukami, H.; Ninomiya, K.; Egawa, M. Substituted (ω-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants. J. Med. Chem. 1984, 27 (5), 645-649.
8. Marinella, R.; Pizzirani, D.; Simoni, D.; Rondanin, R.; Baruchello, R.; Bonora, C.; Buscemi, F.; Grimaudo, S.; Tolomeo, M. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 2003, 46(16), 3546-3554.
9. Ali, M. A.; Kondo, K.; Tsuda, Y. Synthesis and nematocidal activity of hydroxystilbenes. Chem. Pharm. Bull. 1992, 40 (5), 1130-1136.
10. 13C study of some (E)-3′- and 4′-substituted stilben-4-ols. Magn. Reson. Chem. 1991, 29 (9), 966-968.
11. 13C NMR spectra of resveratrol derivatives. Magn. Reson. Chem. 2001, 39 (12), 768-770.
12. Wyrzykiewicz, E.; Łapucha, A.; Sylwestrzak, U. Carbon-13 chemical shift assignment of E-hydroxyazastilbenes. Org. Magn. Reson. 1984, 22 (4), 272-273.
13. Güsten, H.; Salzwedel, M. Die Kemmagnetischen Resonanzspektren Substituierter trans-Stilbene. Tetrahedron 1967, 23, 173-191.
14. 13C NMR spectra of trans-stilbene. Org. Magn. Reson. 1984, 22 (4), 237-244.
15. 13C NMR spectra of 4,4′-substituted chalcones. Magn. Reson. Chem. 1989, 27 (9), 899-904.
16. 13C nuclear magnetic resonance studies on 1,3-diphenylprop-2-enones. Magn. Reson. Chem. 1990, 28 (5), 470-474.
17. 13C n.m.r. spectroscopy. Org. Magn. Reson. 1976, 8 (9), 439-443.
18. 1H NMR spectra of chalcones. Org. Magn. Reson. 1980, 14 (2), 138-140.
19. Silva, A. M.; Tavares, H. R.; Barros, A. I.; Cavaleiro, J. A. NMR and structural and conformational features of 2′-hydroxychalcones and flavones. Spectrosc. Lett. 1997, 30(8), 1655-1667.
20. Nowakowska, Z. New method of the synthesis of chalconethiols and stilbenethiols, In Proceedings of the XLV Congress of the Polish Chemical Society; Kraków, Poland, Sept. 9-13, 2002, Polish Chemical Society: Kraków, 196-197.
21. Newman, M. S.; Karnes, H. A. The conversion of phenols to thiophenols via Dialkylthiocarbamates. J. Org. Chem. 1966, 31 (12), 3980-3984.