Collect. Czech. Chem. Commun. 2006, 71, 709-722
https://doi.org/10.1135/cccc20060709

Preparation of 1-Adamantyl Ketones: Structure, Mechanism of Formation and Biological Activity of Potential By-Products

Robert Víchaa, Marek Nečasb and Milan Potáčekc,*

a Department of Food Engineering and Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Náměstí T.G.M. 275, 762 72 Zlín, Czech Republic
b Department of Inorganic Chemistry, Faculty of Science, Masaryk University Brno, Kotlářská 2, 611 37 Brno, Czech Republic
c Department of Organic Chemistry, Faculty of Science, Masaryk University Brno, Kotlářská 2, 611 37 Brno, Czech Republic

References

1. Aldrich P. A., Hermann E. C., Meier W. E., Paulshock M., Prichard W. W., Snyder J. A., Watts J. C.: J. Med. Chem. 1971, 14, 535. <https://doi.org/10.1021/jm00288a019>
2. Davies W. L., Grunert R. R., Haff R. F., Paulshock J., Walts J. C., Word T. R., Hermann E. C., Hoffmann C. E.: Science 1964, 144, 862. <https://doi.org/10.1126/science.144.3620.862>
3. Oker-Blom N., Anderson A. L.: Eur. J. Cancer 1966, 2, 9. <https://doi.org/10.1016/0014-2964(66)90084-3>
4. Lundahl K., Schut J., Schlatmann J. L. M. A., Paerels G. B., Peters A.: J. Med. Chem. 1972, 15, 129. <https://doi.org/10.1021/jm00272a003>
5. Lasek W., Switaj T., Sienko J., Kasprzycka M., Basak G., Miklaszewicz P., Maj M., Nowis D., Grzela T., Golab J., Mlynarczuk I., Jalili A., Kaminska B., Dziembowska M., Czajkowski K., Nowaczyk M., Gorska A., Kazimierczuk Z.: Cancer Chemother. Pharm. 2002, 50, 213. <https://doi.org/10.1007/s00280-002-0496-5>
6. El-Sherbeny M. A.: Med. Chem. Res. 2002, 11, 74.
7. Gerzon K., Krumkalns E. V., Brindle R. L., Marshall F. J., Root M. A.: J. Med. Chem. 1963, 6, 760. <https://doi.org/10.1021/jm00342a029>
8. Rogóż Z., Dlaboga M., Dziedzicka-Wasylewska M.: J. Physiol. Pharmacol. 2003, 54, 257.
9. Chakrabarti J. K., Foulis M. J., Hotten T. M., Szinai S. S., Todd A.: J. Med. Chem. 1974, 17, 602. <https://doi.org/10.1021/jm00252a007>
10. Orzeszko A., Kamińska B., Starościak B.: Farmaco 2002, 57, 619. <https://doi.org/10.1016/S0014-827X(02)01199-0>
11. Ilies M. A., Masereel B., Rolin S., Scozzafava A., Câmpeanu G., Cîmpeanu V., Supuran C. T.: Bioorg. Med. Chem. 2004, 12, 2717. <https://doi.org/10.1016/j.bmc.2004.03.008>
12. Spasov A. A., Khamidova T. V., Bugaeva L. I., Morozov I. S.: Khim.-Farm. Zh. 2000, 34, 3.
13. Kato N., Eggers H.: Virology 1969, 37, 632. <https://doi.org/10.1016/0042-6822(69)90281-5>
14. Kiselev O. I., Blinov V. M., Kozeletskaya K. N., Ilenko V. I., Platonov V. G., Chupakhin O. N., Stukova M. A., Karginov V. A.: Vestn. Ross. Akad. Med. Nauk 1993, 1015.
15. Sasaki T., Simizu K.: Chem. Pharm. Bull. 1984, 4, 1433. <https://doi.org/10.1248/cpb.32.1433>
16. Cahiez G., Laboue B.: Tetrahedron Lett. 1992, 33, 4439. <https://doi.org/10.1016/S0040-4039(00)60104-1>
17. Vícha R., Potáček M.: Tetrahedron 2005, 61, 83. <https://doi.org/10.1016/j.tet.2004.10.059>
18. Hatano M., Matsumura T., Ishihara K.: Org. Lett. 2005, 7, 573. <https://doi.org/10.1021/ol047685i>
19. Tuulmets A., Sassian M.: J. Organomet. Chem. 1999, 586, 145. <https://doi.org/10.1016/S0022-328X(99)00254-5>
20. Ashby E. C., Goel A. B.: J. Am. Chem. Soc. 1981, 103, 4983. <https://doi.org/10.1021/ja00406a070>
21. Greene J. L., Abraham D., Zook H. D.: J. Org. Chem. 1959, 24, 132. <https://doi.org/10.1021/jo01083a624>
22. Whitmore F. C., Wheeler W. R.: J. Am. Chem. Soc. 1938, 60, 2899. <https://doi.org/10.1021/ja01279a018>
23. Alper H., Huang C.-C.: J. Org. Chem. 1973, 38, 64. <https://doi.org/10.1021/jo00941a012>
24. Ganem B., Small V. R.: J. Org. Chem. 1974, 39, 3728. <https://doi.org/10.1021/jo00939a026>
25. Green L., Hemeon I., Singer R. D.: Tetrahedron Lett. 2000, 41, 1343. <https://doi.org/10.1016/S0040-4039(99)02289-3>
26. Porter C. W., Steel C.: J. Am. Chem. Soc. 1920, 42, 2650. <https://doi.org/10.1021/ja01457a024>
27. Goebel M. T., Marvel C. S.: J. Am. Chem. Soc. 1933, 55, 1693. <https://doi.org/10.1021/ja01331a065>
28. Marchand A. P., Xing D., Bott S. G.: Tetrahedron 1996, 52, 825. <https://doi.org/10.1016/0040-4020(95)00934-5>
29. Reith B. A., Strating J., Van Leusen A. M.: J. Org. Chem. 1974, 39, 2728. <https://doi.org/10.1021/jo00932a013>
30. Shiner V. J., Neumann T. E.: Croat. Chem. Acta 1996, 69, 1405.
31. Dua S., Bowie J. H.: J. Chem. Soc., Perkin Trans. 2 1998, 1443. <https://doi.org/10.1039/a708654g>
32. Hoffmann H. M. R., Haase K.: Synthesis 1981, 715. <https://doi.org/10.1055/s-1981-29573>
33. Novakov C. P., Feierman D., Cederbaum A. I., Stoyanovsky D. A.: Chem. Res. Toxicol. 2001, 14, 1239. <https://doi.org/10.1021/tx015507h>
34. Gilman H., Wilkinson P. D., Fishel W. P., Meyers C. H.: J. Am. Chem. Soc. 1923, 45, 150. <https://doi.org/10.1021/ja01654a022>
35. Grava I. Ya., Polis Ya. Yu., Lubak M. Yu., Lieninsh E. E., Shamc V. D., Dipan I. V., Gavars M. P., Cekacis I. P.: Zh. Org. Khim. 1981, 17, 778.
36. Kraus G. A., Siclovan T. M.: J. Org. Chem. 1994, 59, 922. <https://doi.org/10.1021/jo00083a038>
37. Lednicer D., Heyd W. E., Emmert D. E., TenBrink R. E., Schurr P. E., Day C. E.: J. Med. Chem. 1979, 22, 69. <https://doi.org/10.1021/jm00187a016>
38. Rieke R. D., Hanson M. V., Brown J. D., Nium Q. J.: J. Org. Chem. 1996, 61, 2726. <https://doi.org/10.1021/jo952104b>
39. Stetter H., Rauscher E.: Chem. Ber. 1960, 93, 1161. <https://doi.org/10.1002/cber.19600930527>
40. Molle G., Briand S., Bauer P., Dubois J.-E.: Tetrahedron 1984, 40, 5113. <https://doi.org/10.1016/S0040-4020(01)91260-8>