Aminomethylation of the natural isoflavonoid sophoricoside (genistein-4-O-β-D-glucoside) was studied. It was shown that the most convenient method for performing the aminomethylation was the use of aminals. 6,8-bis-Substituted derivatives of sophoricoside were synthesized.
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J.-H. Wang, F.-C. Lou, Y.-L. Wang, and Y.-P. Tang, Phytochemistry, 63(4), 463 (2003).
A. A. Tulaganov and D. T. Gaibnazarova, Khim.-farm. Zh., 35(8), 28 (2001).
Y. Tang, F. Lou, J. Wang, and S. Zhuang, J. Nat. Prod., 64(8), 1107 (2001).
B. Min, S. R. Oh, H.-K. Lee, K. Takatsu, I.-M. Chang, K. R. Min, and Y. Kim, Planta Med., 65, 408 (1999).
V. G. Pivovarenko, A. V. Tuganova, L. F. Osinskaya, and Yu. D. Kholodova, Khim.-farm. Zh., 31(3), 14 (1997).
R. R. Paris, G. Faugeras, and J.-F. Dombremes, Planta Med., 29, 32 (1976).
Y. Katagiri, R. K. Ibrahim, and S. Tahara, Biosci. Biotechnol. Biochem., 64, 1118 (2000).
B. H. Kim, E. Y. Chung, B.-K. Min, S. H. Lee, M.-K. Kim, K. R. Min, and Y. Kim, Planta Med., 69, 474 (2003).
J. Yun, S. R. Oh, H.-K. Lee, I.-M. Chang, K. Takatsu, Y.-P. Yun, K. R. Min, and Y. Kim, Planta Med., 67, 274 (2001).
S.-H. Jung, S.-H. Cho, T. H. Dang, J.-H. Lee, J.-H. Ju, M.-K. Kim, S.-H. Lee, J.-C. Ryu, and Y. Kim, Eur. J. Med. Chem., 38(5), 537 (2003).
M. Shimizu, T. Ito, S. Terashima, T. Hayashi, M. Arisava, N. Morita, S. Kurokawa, K. Ito, and Y. Hashimoto, Phytochemistry 23(9), 1885 (1984).
I. Setnikar, W. Murmann, M. J. Magistretti, P. Da Re, and L. Verlicchi, J. Med. Pharm. Chem., 3, 471 (1961).
P. Da Re, I. Setnikar, and L. Verlicchi, J. Org. Chem., 25(7), 1097 (1960).
T. Liu, Z. Xu, Q. He, Y. Chen, B. Yang, and Y. Hu, Bioorg. Med. Chem. Lett., 17, 278 (2007).
V. A. Bandyukova, Rastit. Resur., 4(1), 97 (1968).
M. Tramontini, Synthesis, 703 (1973).
F. Kallay and G. Janzo, Tetrahedron Lett., 19, 1443 (1978).
S. P. Bondarenko, A. V. Levenets, M. S. Frasinyuk, and V. P. Khilya, Khim. Prir. Soedin., 211 (2003).
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2012, pp. 29–31.
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Bondarenko, S.P., Frasinyuk, M.S. & Khilya, V.P. Synthesis of aminomethyl derivatives of sophoricoside. Chem Nat Compd 48, 26–29 (2012). https://doi.org/10.1007/s10600-012-0151-2
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DOI: https://doi.org/10.1007/s10600-012-0151-2