Synthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1674-1677

  Morera, Enrico ^a   De Petrocellis, Luciano ^b   Morera, Ludovica ^a   Moriello, Aniello Schiano ^b   Nalli, Marianna ^a   Di Marzo, Vincenzo ^b   Ortar, Giorgio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CNR   (Italy)

Author keywords

Gingerol analogues; Shogaol analogues; TRP channels; TRPV1; TRPA1

Indexed keywords

(6) GINGEROL; ALLYL ISOTHIOCYANATE; CAPSAICIN; SHOGAOL; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1; TRANSIENT RECEPTOR POTENTIAL CHANNEL A1 AGONIST; TRANSIENT RECEPTOR POTENTIAL CHANNEL AFFECTING AGENT; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR AGONIST;

ALDOL REACTION; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; LIPOPHILICITY; STRUCTURE ACTIVITY RELATION;

EID: 84856677167     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.113     Document Type: Article

References (36)

1. (a) Tapsell, L. C.; Hemphill, I.; Cobiac, L.; Patch, C. S.; Sullivan, D. R.; Fenech, M.; Roodenrys, S.; Keogh, J. B.; Clifton, P. M.; Williams, P. G.; Fazio, V. A.; Inge, K. E. Med. J. Aust. 2006, 185, S4
2. (b) Chrubasik, S.; Pittler, M. H.; Roufogalis, B. D. Phytomedicine 2005, 12, 684
3. (c) Wang, W. H.; Wang, Z. M. Zhongguo Zhong Yao Za Zhi 2005, 30, 1569.
4. (a) Butt, M. S.; Sultan, M. T. Crit. Rev. Food Sc. Nutr. 2011, 51, 383
5. (b) Ali, B. H.; Blunden, G.; Tanira, M. O.; Nemmar, A. Food Chem. Toxicol. 2008, 46, 409.
6. Lee, H. S.; Seo, E. Y.; Kang, N. E.; Kim, W. K. J. Nutr. Biochem. 2008, 19, 313.
7. Rhode, J.; Fogoros, S.; Zick, S.; Wahl, H.; Griffith, K. A.; Huang, J.; Liu, J. R. BMC Complement. Altern Med. 2007, 7, 44.
8. Kiuchi, F.; Iwakami, S.; Shibuya, M.; Hanaoka, F.; Sankawa, U. Chem. Pharm. Bull. 1992, 40, 387.
9. Yasuka Isa, Y.; Miyakawa, Y.; Yanagisawa, M.; Goto, T.; Kang, M.-S.; Kawada, T. Biochem. Biophys. Res. Commun. 2008, 373, 429.
10. (a) Iwasaki, Y.; Morita, A.; Iwasawa, T.; Kobata, K.; Sekiwa, Y.; Morimitsu, Y.; Kubota, K.; Watanabe, T. Nutr. Neurosci. 2006, 9, 169
11. (b) Dedov, V. N.; Tran, V. H.; Duke, C. C.; Connor, M.; Christie, M. J.; Mandadi, S.; Roufogalis, B. D. Br. J. Pharmacol. 2002, 137, 793.
12. Bandell, M.; Story, G. M.; Hwang, S. W.; Viswanath, V.; Eid, S. R.; Petrus, M. J.; Earley, T. J.; Patapoutian, A. Neuron 2004, 41, 849.
13. (a) Li, M.; Yu, Y.; Yang, J. Adv. Exp. Med. Biol. 2011, 704, 1
14. (b) Vennekens, R.; Owsianik, G.; Nilius, B. Curr. Pharm. Des. 2008, 14, 18
15. (c) Appendino, G.; Minassi, A.; Pagani, A.; Ech-Chahad, A. Curr. Pharm. Des. 2008, 14, 2
16. (d) Venkatachalam, K.; Montell, C. Annu. Rev. Biochem. 2007, 76, 387
17. (e) Gharat, L.; Szallasi, A. Drug Develop. Res. 2007, 68, 477
18. (f) Minke, B. Cell Calcium 2006, 40, 261.
19. (a) Moran, M. M.; McAlexander, M. A.; Bíró, T.; Szallasi, A. Nat. Rev. Drug Discov. 2011, 10, 601;
20. (b) Baraldi, P. G.; Preti, D.; Materazzi, S.; Geppetti, P. J. Med. Chem. 2010, 53, 5085
21. (c) Di Marzo, V.; De Petrocellis, L. Curr. Med. Chem. 2010, 17, 1430
22. (d) Vay, L.; Gu, C.; McNaughton, P. A. Expert Rev. Clin. Pharmacol. 2010, 3, 687
23. (e) Trevisani, M.; Szallasi, A. Open Drug Discov. J. 2010, 2, 37
24. (f) Cortright, D. N.; Szallasi, A. Curr. Pharm. Des. 2009, 15, 1736
25. (g) Patapoutian, A.; Tate, S.; Woolf, C. J. Nat. Rev. Drug Discov. 2009, 8, 55
26. (h) Gunthorpe, M. J.; Szallasi, A. Curr. Pharm. Des. 2008, 14, 32
27. (i) Westaway, S. M. J. Med. Chem. 2007, 50, 2589.
28. Lee, S. P.; Buber, M. T.; Yang, Q.; Cerne, R.; Cortes, R. Y.; Sprous, D. G.; Bryant, R. W. Br. J. Pharmacol. 2008, 153, 1739.
29. Oyagbemi, A. A.; Saba, A. B.; Azeez, O. I. BioFactors 2010, 36, 169.
30. Morita, A.; Iwasaki, Y.; Kobata, H.; Yokogoshi, H.; Watanabe, T. Biosci. Biotechnol. Biochem. 2007, 71, 2304.
31. (a) Walpole, C. S. J.; Wrigglesworth, R.; Bevan, S.; Campbell, E. A.; Dray, A.; James, I. F.; Perkins, M. N.; Reid, D. J.; Winter, J. J. Med. Chem. 1993, 36, 2362
32. (b) Walpole, C. S. J.; Wrigglesworth, R.; Bevan, S.; Campbell, E. A.; Dray, A.; James, I. F.; Masdin, K. J.; Perkins, M. N.; Winter, J. J. Med. Chem. 1993, 36, 2373
33. (c) Walpole, C. S. J.; Wrigglesworth, R.; Bevan, S.; Campbell, E. A.; Dray, A.; James, I. F.; Masdin, K. J.; Perkins, M. N.; Winter, J. J. Med. Chem. 1993, 36, 2381.
34. McNamara, F. N.; Randall, A.; Gunthorpe, M. J. Br. J. Pharm. 2005, 144, 781.
35. Denniff, P.; Macleod, I.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1980, 82.
36. Correa, E. A.; Högestätt, E. D.; Sterner, O.; Echeverri, F.; Zygmunt, P. M. Bioorg. Med. Chem. 2010, 18, 3299.