Synthesis, physical properties, and cytotoxicity of Nitroxyl-Aziridine hybrid

Helvetica Chimica Acta

Volumn 93, Issue 11, 2010, Pages 2109-2114

  Kumamoto, Takuya ^a   Suzuki, Kazuya ^a   Kim, Sang Kook ^a   Hoshino, Katsuyoshi ^a   Takahashi, Masahiro ^a   Sato, Hiromi ^a   Iwata, Hiroki ^a   Ueno, Koichi ^a   Fukuzumi, Masahiro ^a   Ishikawa, Tsutomu ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Aziridine; Cyclic voltammetry; Cytotoxicity; Electron spin resonance (ESR); Nitroxyl

Indexed keywords

ANTICANCER DRUG; AZIRIDINES; CANCER CELL LINES; CHIRAL GUANIDINIUM; CYCLIC VOLTAMMOGRAMS; DIASTEREO-SELECTIVITY; DIASTEREOISOMERS; ELECTRON SPIN RESONANCE; ELECTRON SPIN RESONANCE (ESR); FORMATION REACTION; GUANIDINIUM; NITROXYL; OPTICALLY ACTIVE; REDOX POTENTIALS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ALDEHYDES; CELL CULTURE; CYTOTOXICITY; ELECTRONS; MAGNETIC RESONANCE IMAGING; REDOX REACTIONS; RESONANCE; SPIN DYNAMICS; SYNTHESIS (CHEMICAL);

CYCLIC VOLTAMMETRY;

3 ALKENYLAZIRIDINE 2 CARBOXYLATE DERIVATIVE; 3 ARYLAZIRIDINE 2 CARBOXYLATE DERIVATIVE; 3 FORMYL 2,5 DIHYDRO 2,2,5,5 TETRAMETHYL 1H PYRROL 1 YLOXYL; [3 [1 BENZYL 3 [(TERT BUTOXY)CARBONYL]AZIRIDIN 2 YL] 2,2,5,5 TETRAMETHYL 2,5 DIHYDRO 1H PYRROL 1 YL]OXIDANYL; ALDEHYDE; AZIRIDINE; AZIRIDINE DERIVATIVE; GUANIDINE; GUANIDINIUM YLIDE; TEMPOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIC POTENTIOMETRY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; NUCLEAR MAGNETIC RESONANCE IMAGING; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 78549292799     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000076     Document Type: Article

References (25)

1. O. H. Griffith, A. S. Waggoner, Acc. Chem. Res. 1969, 2, 17.
2. A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4983
3. V. W. Bowry, K. U. Ingold, J. Am. Chem. Soc. 1992, 114, 4992.
4. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051.
5. M. C. Krishna, W. DeGraff, O. H. Hankovszky, C. P. Sár, T. Kálai, J. Jeko, A. Russo, J. B. Mitchell, K. Hideg, J. Med. Chem. 1998, 41, 3477.
6. C. S. Winalski, S. Shortkroff, R. V. Mulkern, E. Schneider, G. M. Rosen, Magn. Reson. Med. 2002, 48, 965.
7. P. M. Blagoeva, Z. D. Raikov, I. Chernozemsky, I. Nikolov, N. D. Yordanov, Cancer Biochem. Biophys. 1979, 3, 169.
8. A. M. Zheleva, V. G. Gadjeva, Int. J. Pharm. 2001, 212, 257.
9. K.-K. Lu, Y.-G. Wang, Y.-Z. Chen, Synth. Commun. 1997, 27, 1963.
10. Z. Zhelev, R. Bakalova, I. Aoki, K.-I. Matsumoto, V. Gadjeva, K. Anzai, I. Kanno, Mol. Pharmaceutics 2009, 6, 504.
11. M. P. Sykes, D. A. Karnofsky, F. S. Philips, J. H. Burchenal, Cancer 1953, 6, 142.
12. T. Hata, T. Hoshi, K. Kanamori, A. Matsumae, Y. Sano, T. Shima, R. Sugawara, J. Antibiot. 1956, 9, 141
13. S. Wakaki, H. Marumo, K. Tomioka, G. Shimizu, E. Kato, H. Kamada, S. Kudo, Y. Fujimoto, Antibiot. Chemother. 1958, 8, 228.
14. K. Hada, T. Watanabe, T. Isobe, T. Ishikawa, J. Am. Chem. Soc. 2001, 123, 7705
15. T. Haga, T. Ishikawa, Tetrahedron 2005, 61, 2857
16. W. Disadee, T. Ishikawa, J. Org. Chem. 2005, 70, 9399
17. W. Disadee, T. Ishikawa, M. Kawahata, K. Yamaguchi, J. Org. Chem. 2006, 71, 6600
18. T. Manaka, S. Nagayama, W. Desadee, N. Yajima, T. Kumamoto, T. Watanabe, T. Ishikawa, M. Kawahata, K. Yamaguchi, Helv. Chim. Acta 2007, 90, 128
19. T. Kumamoto, S. Nagayama, Y. Hayashi, H. Kojima, D. Lemin, W. Nakanishi, T. Ishikawa, Heterocycles 2008, 76, 1155.
20. S. W. Stork, M. W. Makinen, Synthesis 1999, 1309.
21. J. P. Blinco, J. L. Hodgson, B. J. Morrow, J. R. Walker, G. D. Will, M. L. Coote, S. E. Bottle, J. Org. Chem. 2008, 73, 6763.
22. A. Rockenbauer, M. Györ, K. Hideg, H. O. Hankovszky, J. Chem. Soc., Chem. Commun. 1985, 1651.
23. S. D. Rychnovsky, T. L. McLernon, H. Rajapakse, J. Org. Chem. 1996, 61, 1194
24. Y. Kashiwagi, F. Kurashima, C. Kikuchi, J.-I. Anzai, T. Osa, J. M. Bobbitt, Tetrahedron Lett. 1999, 40, 6469
25. M. Tomizawa, M. Shibuya, Y. Iwabuchi, Org. Lett. 2009, 11, 1829.