The synthesis of 10-carbonyl and 10-carboxylic derivatives of para-mentha-1,8-diene-5,6-diol (1) that exhibited high anti-Parkinson’s activity was described. The synthesis of these compounds was an important programmatic component in a study of the metabolism of 1.
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O. V. Ardashov, A. V. Pavlova, I. V. Il’ina, E. A. Morozova, D. V. Korchagina, E. V. Karpova, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, J. Med. Chem., 54 (11), 3866 (2011).
T. G. Tolstikova, A. V. Pavlova, E. A. Morozova, O. V. Ardashov, I. V. Il’ina, K. P. Volcho, N. F. Salakhutdinov, and G. A. Tolstikov, Dokl. Akad. Nauk Fiziol., 435 (5), 708 (2010).
O. V. Ardashov, A. V. Pavlova, D. V. Korchagina, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, Med. Chem., 9 (5), 731 (2013).
W. Engel, J. Agric. Food Chem., 49, 4069 (2001).
T. Ishida, M. Toyota, and Y. Asakawa, Xenobiotica, 19, 843 (1989).
J. W. Regan and L. F. Bjeldanes, J. Agric. Food Chem., 24 (2), 4069 (1976).
M. Yazawa, M. Shindo, and T. Shimada, Drug Metab. Dispos., 30 (5), 602 (2002).
O. V. Ardashov, A. V. Pavlova, D. V. Korchagina, K. P. Volcho, T. G. Tolstikova, and N. F. Salakhutdinov, Bioorg. Med. Chem., 21 (5), 1082 (2013).
O. V. Ardashov, E. V. Khaid, O. S. Mikhal’chenko, D. V. Korchagina, K. P. Volcho, and N. F. Sakakhutdinov, Izv. Akad. Nauk, Ser. Khim., 62 (1), 172 (2013) [O. V. Ardashov, E. V. Khaid, O. S. Mikhal’chenko, D. V. Korchagina, K. P. Volcho, and N. F. Salakhutdinov, Russ. Chem. Bull., 62 (1), 171 (2013)].
O. V. Ardashov, K. P. Volcho, and N. F. Salakhutdinov, Usp. Khim., 83 (4), 281 (2014) [O. V. Ardashov, K. P. Volcho, and N. F. Salakhutdinov, Russ. Chem. Rev., 83 (4), 281 (2014)].
M. von Montavon, H. Lindlar, R. Marbet, R. Ruegg, G. Ryser, G. Saucy, P. Zeller, and O. Isler, Helv. Chim. Acta, 49 (140), 1250 (1957).
E. Vedejs, D. M. Gapinski, and J. P. Hagen, J. Org. Chem., 46, 5452 (1981).
D. Xu, T. M. Penning, I. A. Blair, and R. G. Harvey, J. Org. Chem., 74 (2), 597 (2009).
A. G. Godfrey and B. Ganem, Tetrahedron Lett., 31 (34), 4825 (1990).
M. Miyashita, A. Yoshikoshi, and P. A. Grieco, J. Org. Chem., 42 (23), 3772 (1977).
M. Isobe, H. Iio, T. Kawai, and T. Goto, J. Am. Chem. Soc., 100 (6), 1942 (1978).
T. Mineno, Tetrahedron Lett., 43, 7975 (2002).
I. E. Marco, A. Ates, B. Augustyns, A. Gautier, Y. Quesnel, L. Turet, and M. Wiaux, Tetrahedron Lett., 40, 5613 (1999).
F. A. Gimalova, G. M. Khalikova, S. A. Torosyan, D. Z. Akhmetshina, and M. S. Miftakhov, Zh. Org. Khim., 48 (2), 194 (2012) [F. A. Gimalova, G. M. Khalikova, S. A. Torosyan, D. Z. Akhmetshina, and M. S. Miftakhov, Russ. J. Org. Chem., 48 (2), 180 (2012)].
S. B. Balkrishna, E. C. Wayne, and H. W. Pinnick, Tetrahedron, 37, 2091 (1981).
I. A. Pearl, J. Am. Chem. Soc., 68, 429 (1946).
Q. Wang, S. Y. Fan, H. N. C. Wong, Z. Li, B. M. Fung, R. J. Twieg, and H. T. Nguyen, Tetrahedron, 49 (3), 619 (1993).
M. Kawaguchi, O. Hayashi, N. Sakai, M. Hamada, Y. Yamamoto, and J. Oda, Agric. Biol. Chem., 50 (12), 3107 (1986).
T. Kitahara, A. Horiguchi, and K. Mori, Tetrahedron, 44 (15), 4713 (1988).
X. Cong and Z.-J. Yao, J. Org. Chem., 71, 5365 (2006).
Q. Yang, C. Draghici, J. T. Njardarson, F. Li, B. R. Smith, and P. Das, Org. Biomol. Chem., 12, 330 (2014).
D. Askin, C. Angst, and S. Danishefsky, J. Org. Chem., 52, 622 (1987).
R. R. Gowda and D. Chakraborty, Chin. J. Chem., 29, 2379 (2011).
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We thank the Russian Federation Ministry of Education and Science for financial support.
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2015, pp. 419–423.
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Ardashov, O.V., Korchagina, D.V., Volcho, K.P. et al. Synthesis of 10-Carbonyl and 10-Carboxylic Derivatives of para-Mentha-1,8-Diene-5,6-Diol. Chem Nat Compd 51, 483–487 (2015). https://doi.org/10.1007/s10600-015-1320-x
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DOI: https://doi.org/10.1007/s10600-015-1320-x


