Starting materials of phosphasugars, 1-phenyl-2-phospholene 1-oxides, were prepared from dienes and phenylphosphonous dichloride (dichlorophenylphosphine). Several substituted novel phosphasugars (3- or 4-halo-substituted)-1-phenyl-2-phospholene 1-oxides as well as 1-phenyl-2-phospholane 1-oxides were prepared from 2-phospholenes. The synthesized compounds were evaluated for their antitumor activities against the leukemia cell lines (U937 and K562) by in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. 2,3,4-Tribromo-3-methyl-1-phenylphospholane 1-oxide showed superior antitumor activity against U937 and K562 cell lines in a comparative evaluation with Glivec. The analysis by flow cytometry implied that 2,3-dibromo-3-methyl-1-phenylphospholane 1-oxide induced apoptosis to leukemia cell lines.
Conference
European Carbohydrate Symposium (Eurocarb-16), 16th, Sorrento, Italy, 2011-07-03–2011-07-07
References
1 S. Inouye, T. Tsuruoka, T. Ito, T. Niida. Tetrahedron24, 212 (1968).10.1016/0040-4020(68)88115-3Search in Google Scholar
2 10.1039/a809398i, H. Seto, T. Kuzuyama. Nat. Prod. Rep.16, 589 (1999).Search in Google Scholar
3 10.1126/science.166.3901.122, D. Hendlin, D. O. Stapley, M. Jackson, H. Wallick, A. K. Miller, F. J. Wolf, T. W. Miller, L. Chaiet, F. M. Kahan, E. L. Foltz, H. B. Woodruff, S. Mochales. Science166, 122 (1969).Search in Google Scholar
4 H. Nakashita, K. Watanabe, O. Hara, T. Hidaka, H. Seto. J. Antibiot.50, 212 (1997).10.7164/antibiotics.50.212Search in Google Scholar
5 10.1021/ol801106r, M. Shan, G. A. O’Doherty. Org. Lett.10, 3381 (2008).Search in Google Scholar
6 10.1002/ejoc.200800649, M. A. Alam, A. Kumar, Y. D. Vankar. Eur. J. Org. Chem.29, 4972 (2008).Search in Google Scholar
7 10.1021/ol016970o, B. G. Davis, M. A. Maughan, T. M. Chapman, R. Villard, S. Courtney. Org. Lett.4, 103 (2002).Search in Google Scholar
8 10.1021/jo00893a021, M. Chmielewski, R. L. Whistler. J. Org. Chem.40, 639 (1975).Search in Google Scholar
9 10.1021/jo9812330, P. Wang, L. A. Agrofoglio, M. G. Newton, C. K. Chu. J. Org. Chem.64, 4173 (1999).Search in Google Scholar
10 10.1016/0008-6215(84)85084-3, G. Legler, E. Julich. Carbohydr. Res.128, 61 (1984).Search in Google Scholar
11 10.1021/jo00086a032, J. Braanalt, I. Kvarnstroem, G. Niklasson, S. C. T. Svensson, B. Classon, B. Samuelsson. J. Org. Chem.59, 1783 (1994).Search in Google Scholar
12 M. Yamashita, Y. Kato, K. Suzuki, T. Oshikawa. Heterocycl. Commun.4, 411 (1998).Search in Google Scholar
13 10.1021/jo00219a018, H. Yamamoto, T. Hanaya, H. Kawamoto, S. Inokawa, M. Yamashita, M. A. Armour, T. T. Nakashima. J. Org. Chem.50, 3516 (1985).Search in Google Scholar
14 10.1016/j.tetlet.2004.01.139, V. K. Reddy, B. Haritha, T. Oshikawa, M. Yamashita. Tetrahedron Lett.45, 2851 (2004).Search in Google Scholar
15 10.1021/jo01276a033, R. L. Whistler, C. C. Wang. J. Org. Chem.33, 4455 (1968).Search in Google Scholar
16 10.1016/S0008-6215(00)83321-2, M. Yamashita, Y. Nakatsukasa, M. Yoshikane, H. Yoshida, T. Ogata, S. Inokawa. Carbohydr. Res.59, 12 (1977).Search in Google Scholar
17 10.1007/s10637-009-9255-3, S. Nakamura, M. Yamashita, D. Yokota, I. Hirano, T. Ono, M. Fujie, K. Shibata, T. Niimi, T. Suyama, K. Maddali, K. Asai, J. Yamashita, Y. Iguchi, K. Ohnishi. Invest. New Drugs28, 381 (2010).Search in Google Scholar PubMed
18 10.1158/0008-5472.CAN-06-1199, M. Puttini, A. L. Coluccia, F. Boschelli, L. Cleris, E. Marchesi, A. Donella-Deana, S. Ahmed, S. Redaelli, R. Piazza, V. Magistroni. Cancer Res.66, 11314 (2006).Search in Google Scholar PubMed
19 M. Yamada, K. Asai, J. Yamashita, T. Suyama, T. Niimi, K. Maddali, M. Fujie, S. Nakamura, M. Kimura, Y. Tanaka, M. Toda, M. Yamashita. Heterocycl. Commun.16, 173 (2010).10.1515/HC.2010.16.2-3.173Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston