Synthesis and properties of 11-(3,5-di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid, a new amphiphilic antioxidant

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 6, 2003, Pages 1179-1182

  Lodyato, Vladimir I ^a   Yurkova, Irina L ^a   Sorokin, Viktor L ^a   Shadyro, Oleg I ^a   Dolgopalets, Vladimir I ^b   Kisel, Mikhail A ^b  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

11 (3,5 DI TERT BUTYL 2 HYDROXYPHENYLCARBAMOYL)UNDECANOIC ACID; AMPHOPHILE; ANTIOXIDANT; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; DERIVATIZATION; DRUG DESIGN; DRUG EFFECT; DRUG SYNTHESIS; HYDROPHOBICITY; LIPID PEROXIDATION;

EID: 0037463782     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00041-6     Document Type: Article

References (25)

1. (a) Slater T.F. Biochem. J. 222:1984;1
2. (b) Niki E. Chem. Phys. Lipids. 44:1987;227
3. (c) Gardner H.W. Free Rad. Biol. Med. 7:1989;65.
4. (a) Sies H. Angew. Chem., Int. Ed. Engl. 25:1986;1058 (b) Halliwell B., Gutteridge J.M.C. Free Radicals in Biology and Medicine, 3rd ed. 1999;Oxford University Press, Oxford.
5. Packer L., Cadenas E. Handbook of Synthetic Antioxidants. 1997;Marcel Dekker, New York.
6. Andersson C.-M., Hallberg A., Hogberg T. Adv. Drug. Res. 28:1996;67.
7. (a) Ross D., Mendiratta S., Qu Z.C. Free Rad. Biol. Med. 26:1999;81
8. (b) Tanaka T., Kusano R., Kouno I. Bioorg. Med. Chem. Lett. 8:1998;1801
9. (c) Hino T., Kawanishi S., Yasui H. Biochem. Biophys. Acta. 1425:1998;47.
10. (a) Nagao A., Terao J. Biochem. Biophys. Res. Commun. 172:1990;385
11. (b) Nifant'ev Å. Å., Predvoditelev D.A., Zolotov M.M. Bioorg. Khim. 7:1981;1100.
12. (c) Àkhrem A.A., Dolgopalets V.I., Kisel M.A., Mezen N.I., Timoshchuk V.A., Fedulov A.S., Shadyro O.I. Bioorg. Khim. 21:1995;391. (in Russian).
13. Nihro Y., Miyataka H., Sudo H., Matsumoto H., Satoh T. Med. Chem. 34:1991;2152.
14. Nihro Y., Furukawa H., Sogawa S., Wang T.C., Miyataka H., Matsumoto H., Miki T., Satoh T. Chem. Pharm. Bull. 42:1994;576.
15. Niki E., Iwatsuki M., Komuro E. Bull. Chem. Soc. Jpn. 68:1995;620.
16. Maslovskaya L.A., Petrikevich D.K., Timoshchuk V.A., Shadyro O.I. Zh. Obshch. Khim. 66:1996;1893. (in Russian).
17. Maslovskaya L.A., Petrikevich D.K., Timoshchuk V.A., Shadyro O.I. Zh. Obshch. Khim. 66:1996;1899. (in Russian).
18. Vol'eva V.B., Prokof'eva T.I., Prokof'ev A.I., Belostotskaya I.S., Kommisarova N.L., Ershov V.V. Izv. Akad. Nauk, Ser. Khim. 1995;1789. (in Russian).
19. +, mp 52°C.
20. Zav'yalov S.I., Kravchenko N.E. Izv. Akad. Nauk SSSR, Ser. Khim. 1988;1696. (in Russian).
21. 17 α-Tocopherol (α-T) was used as a reference compound. Two series of runs were performed: in one of them, concentrations of the antioxidants studied and that of α-T were 0.4 mM, while in the other they were 0.1 mM.
22. Bergelson L.D. Lipid Biochemical Preparations. 1980;Elsevier, Amsterdam.
23. Shadyro O.I., Yurkova I.L., Kisel M.A. Int. J. Radiat. Biol. 78:2002;211.
24. Chan H.W.S., Levett G. Lipids. 12:1977;99.
25. Buege J.A., Aust S.D. Methods Enzymol. 52:1978;302.