A convenient synthesis of 5?-iodoresiniferatoxin (i-rtx)

Natural Product Communications

Volumn 1, Issue 12, 2006, Pages 1147-1150

  Ech Chahad, Abdellah ^a,b   Bouyazza, Lahboub ^a   Appendino, Giovanni ^b  

^a HASSAN 1ST UNIVERSITY   (Morocco)

^b UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

5' iodoresiniferatoxin; Resiniferatoxin; Resiniferonol orthophenylacetate; TRV1; Vanilloid antagonists

Indexed keywords

EID: 74549211613     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600101215     Document Type: Article

References (19)

1. Ashcroft FM. (2006) From molecule to malady. Nature, 440, 440-447.
2. Clapham DE. (2003) TRP channels as cellular sensors. Nature, 426, 517-524.
3. Appendino G, Muñoz E, Fiebich BL. (2003) TRPV1 (vanilloid receptor, capsaicin receptor) agonists and antagonists. Expert Opinion Therapeutic Patents, 13, 1825-1837.
4. Wahl P, Foged C, Tullin S, Thomsen C. (2001) Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Molecular Pharmacology, 59, 9-15.
5. The K(i) value for I-RTX after two hour incubation with cells transfected with TRPV1 has been estimated to be 4.2 pM (Lazar J, Braun DC, Toth A, Wang Y, Pearce LV, Pavlyukovets VA, Blumberg PM, Garfield SH, Wincovitch S, Choi HK, Lee J. (2006) Kinetics of penetration influence the apparent potency of vanilloids on TRPV1. Molecular Pharmacology, 69, 1166-1173).
6. Trevisani M, Milan A, Gatti Z, Zanasi A, Harrison S, Fontana G, Morice AH, Geppetti P. (2004) Antitussive activity of iodoresiniferatoxin in guinea pigs. Thorax, 59, 769-772.
7. Rigoni M, Trevisani M, Mazzieri D, Nadaletto R, Tognetto M, Creminon C, Davis JB, Campi B, Amatesi S, Geppetti P, Harrisnon S. (2003) Neurogenic responses mediated by vanilloid receptor-1 (TRPV1) are blocked by the high affinity antagonist, iodoresiniferatoxin. British Journal of Pharmacology, 138, 977-985.
8. Appendino G, Daddario N, Minassi A, Schiano Morello A, De Petrocellis L, Di Marzo V. (2005) The taming of capsaicin. Reversal of vanilloid activity of N-acylvanillamines by aromatic iodination. Journal of Medicinal Chemistry, 48, 4663-4669.
9. McDonnel ME, Zhang SP, Dubin AE, Dax SL. (2002) Synthesis and in vitro evaluation of a novel iodinated resiniferatoxin derivative that is an agonist at the human vanilloid VR1 receptor. Bioorganic & Medicinal Chemistry Letters, 12, 1189-1192.
10. Seabrook GR, Sutton KG, Jarolimek W, Hollingworth JH, Teague S, Webb J, Clark N, Boyce S, Kerby J, Lai Z, Chou M, Middleton R, Kaczorowski G, Jones AB. (2002) Functional properties of the high-affinity TRPV1 (VR1) vanilloid receptor antagonist (4-hydroxy-5-iodo-3-methoxyphenylacetate ester) iodo- resiniferatoxin. Journal of Pharmacology and Experimental Therapeutics, 303, 1052-1060.
11. The price of RTX in the 2006 Sigma Catalogue is 280,60 Euro/1mg
12. Fattorusso E, Lanzotti V, Taglialatela-Scafati O, Tron GC, Appendino G. (2002) Bisnorsesquiterpenoids from Euphorbia resinifera Berg. and an expeditious procedure to obtain resiniferatoxin from its fresh latex. European Journal of Organic Chemistry,71-78.
13. Castanet A-S, Colobert F, Broutin P-E. (2002) Mild and regioselective iodination of electron-rich aromatics with Niodosuccinimide and catalytic trifluoroacetic acid. Tetrahedron Letters, 43, 5047-5048
14. Appendino G, Minassi A, Daddario N, Bianchi F, Tron GC. (2002) Chemoselective esterification of phenolic acids and alcohols. Organic Letters, 4, 3839-3841.
15. The price of homovanillic acid in the 2006 Aldrich Catalogue is 12,10 Euro/100mg, while 5-iodovanillin is over 50 times cheaper (12,00 Euro/5 g).
16. Aoyama T, Shioiri T. (1980) Trimethylsilyldiazomethane, a new, stable, and safe reagent for the classical Arndt-Eisert synthesis. Tetrahedron Letters, 21, 4461-4462.
17. Newman MS, Beal PF. (1950) An improved Wolff rearrangement in homogeneous medium. Journal of American Chemical Society, 72, 5163-5165.
18. Anderson NG, Lust DA, Colapret KA, Simpson JH, Malley ME, Gougoutas JZ. (1996) Sulfonation with inversion by Mitsunobu reaction: An improvement on the original conditions. Journal of Organic Chemistry, 61, 7955-7962.
19. Eisenbraun EJ. (1973) Cyclooctanone. Organic Synthesis, Collective Volume 5, 310-312.