The reaction of allyl and benzylarsonic acids with thiols: Mechanistic aspects and implications for dioxygen activation by trivalent arsenic compounds

Journal of Inorganic Biochemistry

Volumn 97, Issue 4, 2003, Pages 331-339

  Lala, Maria A ^a   Ioannou, Panayiotis V ^a  

^a UNIVERSITY OF PATRAS   (Greece)

Author keywords

Arsonic acids; Nucleophilic and electrophilic allylic rearrangements; Reactive oxygen species; Thiols

Indexed keywords

4 NITROTHIOPHENOL; ALLYL COMPOUND; ARSENIC DERIVATIVE; ARSONIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; DISULFIDE; OXYGEN; PENICILLAMINE; PENICILLAMINE DERIVATIVE; REACTIVE OXYGEN METABOLITE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; DECOMPOSITION; OXIDATION; REACTION ANALYSIS;

EID: 0142089802     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0162-0134(03)00264-2     Document Type: Article

References (53)

1. Dixon H.B.F. Adv. Inorg. Chem. 44:1997;191.
2. Engel R. Chem. Rev. 77:1977;349.
3. (a) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;41 Wiley, New York, (b) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;25 Wiley, New York, (c) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;68 Wiley, New York, (d) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;66 Wiley, New York.
4. (a) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;41 Wiley, New York, (b) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;25 Wiley, New York, (c) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;68 Wiley, New York, (d) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;66 Wiley, New York.
5. (a) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;41 Wiley, New York, (b) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;25 Wiley, New York, (c) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;68 Wiley, New York, (d) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;66 Wiley, New York.
6. (a) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;41 Wiley, New York, (b) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;25 Wiley, New York, (c) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;68 Wiley, New York, (d) Doak G.O., Freedman L.D. Organometallic Compounds of Arsenic, Antimony, and Bismuth. 1970;66 Wiley, New York.
7. Tsivgoulis G.M., Sotiropoulos D.N., Ioannou P.V. Phosphorus, Sulfur, and Silicon. 55:1991;165.
8. Ioannou P.V. Appl. Organometal. Chem. 14:2000;261.
9. Ioannou P.V., Siskos M.G. Appl. Organometal. Chem. 15:2001;511.
10. Ioannou P.V., Afroudakis P.A., Siskos M.G. Phosphorus, Sulfur, and Silicon. 177:2002;2773.
11. Ali B.R.S., Dixon H.B.F. Eur. J. Biochem. 215:1993;161.
12. Mutenda E.K., Sparkes M.J., Dixon H.B.F. Biochem. J. 310:1995;983.
13. Quinn P.J., McMullan G. Microbiology. 141:1995;721.
14. Cullen W.R., Reimer K.J. Chem. Rev. 89:1989;713.
15. H.J. Barber, J. Chem. Soc. (1929) 1020.
16. H.J. Barber, J. Chem. Soc. (1929) 1024.
17. Serves S.V., Sotiropoulos D.N., Ioannou P.V., Jain M.K. Phosphorus, Sulfur, and Silicon. 81:1993;181.
18. Terzis A., Ioannou P.V. Chem. Phys. Lipids. 117:2002;53.
19. Kordalis N.L., Ioannou P.V. Appl. Organomet. Chem. 14:2000;273.
20. Ioannou P.V. Chem. Phys. Lipids. 117:2002;7.
21. A. von Döllen, H. Strasdeit, Eur. J. Inorg. Chem. (1998) 61.
22. Serves S.V., Charalambidis Y.C., Sotiropoulos D.N., Ioannou P.V. Phosphorus, Sulfur, and Silicon. 105:1995;109.
23. Scott N., Hatlelid K.M., MacKenzie N.E., Carter D.E. Chem. Res. Toxicol. 6:1993;102.
24. Delnomdedieu M., Basti M.M., Otvos J.D., Thomas D.J. Chem.-Biol. Int. 90:1994;139.
25. Harvey S.C. Goodman L.S., Gilman A. The Pharmacological Basis of Therapeutics. 5th Edition: 1975;924-928 Macmillan, New York.
26. Ni Dhubhghaill O.M., Sadler P.J. Struct. Bonding (Berlin). 78:1991;129.
27. Quick A.J., Adams R. J. Am. Chem. Soc. 44:1922;805.
28. 1H FT-NMR Spectra, vol. I, Aldrich, Milwaukee, WI, 1993, Spectrum 118 B.
29. Piffl M., Weston J., Günther W., Anders E. J. Org. Chem. 65:2000;5942.
30. Rabenstein D.L., Theriault Y. Can. J. Chem. 62:1984;1672.
31. Jackman L.M., Sternhell S. Applications of Nuclear Magnetic Resonance in Organic Chemistry. 2nd Edition: 1969;181-183 Pergamon Press, Oxford.
32. (a) March J. Advanced Organic Chemistry. 3rd Edition: 1985;287-290 Wiley-Interscience, New York, (b) March J. Advanced Organic Chemistry. 3rd Edition: 1985;520-521 Wiley-Interscience, New York, (c) March J. Advanced Organic Chemistry. 3rd Edition: 1985;633-635 Wiley-Interscience, New York.
33. (a) March J. Advanced Organic Chemistry. 3rd Edition: 1985;287-290 Wiley-Interscience, New York, (b) March J. Advanced Organic Chemistry. 3rd Edition: 1985;520-521 Wiley-Interscience, New York, (c) March J. Advanced Organic Chemistry. 3rd Edition: 1985;633-635 Wiley-Interscience, New York.
34. (a) March J. Advanced Organic Chemistry. 3rd Edition: 1985;287-290 Wiley-Interscience, New York, (b) March J. Advanced Organic Chemistry. 3rd Edition: 1985;520-521 Wiley-Interscience, New York, (c) March J. Advanced Organic Chemistry. 3rd Edition: 1985;633-635 Wiley-Interscience, New York.
35. A. Cohen, H. King, W.I. Strangeways, J. Chem. Soc. (1931) 3043.
36. (a) Kamai G., Chadaeva N.A. Proc. Acad. Sci. USSR. 115:1957;717 (b) G. Kamai, N.A. Chadaeva, Izv. Kazansk. Filiala Akad. Nauk SSSR, Ser. Khim. Nauk (1957) 69; Chem. Abstr. 54 (1960) 6521c.
37. (a) Kamai G., Chadaeva N.A. Proc. Acad. Sci. USSR. 115:1957;717 (b) G. Kamai, N.A. Chadaeva, Izv. Kazansk. Filiala Akad. Nauk SSSR, Ser. Khim. Nauk (1957) 69; Chem. Abstr. 54 (1960) 6521c.
38. Cullen W.R., McBride B.C., Reglinski J. J. Inorg. Biochem. 21:1984;179.
39. Walace T.J., Schriesheim A., Bartok W. J. Org. Chem. 28:1963;1311.
40. D.Ya. Evdokimov, Med. Prom. S.S.S.R. (1957) 39; Chem. Abstr. 52 (1957) 6723b.
41. D.Ya. Evdokimov, Med. Prom. S.S.S.R. (1957) 39; Chem. Abstr. 52 (1957) 6723b.
42. Hudson R.F. Structure and Mechanism in Organo-Phosphorus Chemistry. 1965;291-292 Academic Press, London.
43. Alcock N.W. Boding and Structure. 1990;221-223 Ellis Horwood, New York.
44. Michaelis A., Paetow U. Justus Liebigs Ann. Chem. 233:1886;60.
45. Tsivgoulis G.M., Sotiropoulos D.N., Ioannou P.V. Phosphorus, Sulfur, and Silicon. 141:1998;97.
46. Soignet S.L., Maslak P., Wang Z.-G., Jhanwar S., Calleja E., Dardashti L.J., Corso D., DeBlasio A., Gabrilove J., Scheinberg D.A., Pandofli P.P., Warrell R.P. New Engl. J. Med. 339:1998;1341.
47. Bode A.M., Dong Z. Crit. Rev. Oncol. Hematol. 42:2002;5.
48. Kitchin K.T. Toxicol. Appl. Pharmacol. 172:2001;249.
49. Thomas D.J., Styblo M., Lin S. Toxicol. Appl. Pharmacol. 176:2001;127.
50. Kitchin K.T., Ahmad S. Toxicol. Lett. 137:2003;3.
51. (a) Yamanaka K., Hoshino M., Okamoto M., Sawamura R., Hasegawa A., Okada S. Biochem. Biophys. Res. Commun. 168:1990;58 (b) Yamanaka K., Okada S. Environ. Health Perspect. 102:(Suppl. 3):1994;37.
52. (a) Yamanaka K., Hoshino M., Okamoto M., Sawamura R., Hasegawa A., Okada S. Biochem. Biophys. Res. Commun. 168:1990;58 (b) Yamanaka K., Okada S. Environ. Health Perspect. 102:(Suppl. 3):1994;37.
53. Yamanaka K., Hasegawa A., Sawamura R., Okada S. Biochem. Biophys. Res. Commun. 165:1988;43.