Antimitotic activity of two macrocyclic bis(bibenzyls), isoplagiochins A and B from the Liverwort Plagiochila fruticosa

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 2, 2009, Pages 493-496

  Morita, Hiroshi ^a   Tomizawa, Yuichiro ^a   Tsuchiya, Tomoe ^a   Hirasawa, Yusuke ^a   Hashimoto, Toshihiro ^b   Asakawa, Yoshinori ^b  

^a HOSHI UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Anti tubulin; Conformation; Isoplagiochin A; Isoplagiochin B; Plagiochila fruticosa; Structure activity relationship

Indexed keywords

ANTIMITOTIC AGENT; AROMATIC COMPOUND; BIBENZYL DERIVATIVE; DIHYDROISOPLAGIOCHIN A; DIHYDROISOPLAGIOCHIN B; ISOPLAGIOCHIN A; ISOPLAGIOCHIN B; MACROCYCLIC COMPOUND; TUBULIN; UNCLASSIFIED DRUG; VINBLASTINE;

ARTICLE; CHEMICAL BOND; DRUG CONFORMATION; DRUG ISOLATION; DRUG POTENCY; IC 50; LIVERWORT; NONHUMAN; POLYMERIZATION; STRUCTURE ACTIVITY RELATION;

HEPATOPHYTA; HYDROGEN BONDING; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MITOSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

PLAGIOCHILA FRUTICOSA; PLAGIOCHILACEAE;

EID: 57749111484     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.036     Document Type: Article

References (23)

1. Iwasaki S. Med. Res. Rev. 13 (1993) 183-198
2. Kavallaris M., Verrills N.M., and Hill B.T. Drug Resist. Updat. 4 (2001) 392-401
3. Some examples. Tinley T.L., R.-Hlubek D.A., Leal R.M., Jackson E.M., Cessac J.W., Quada Jr. J.C., Hemscheidt T.K., and Mooberry S.L. Cancer Res. 63 (2003) 3211-3220
4. Verrills N.M., Flemming C.L., Liu M., Ivery M.T., Cobon G.S., Norris M.D., Haber M., and Kavallaris M. Chem. Biol. 10 (2003) 597-607
5. Hood K.A., West L.M., Rouwé B., Northcote P.T., Berridge M.V., Wakefield J.St., and Miller J.H. Cancer Res. 62 (2002) 3356-3360
6. Hardt I.H., Steinmetz H., Gerth K., Sasse F., Reichenbach H., and Höfle G. J. Nat. Prod. 64 (2001) 847-856
7. Mooberry S.L., Tien G., Hernandez A.H., Plubrukarn A., and Davidson B.S. Cancer Res. 59 (1999) 653-660
8. Hirasawa Y., Izawa E., Matsuno Y., Kawahara N., Goda Y., and Morita H. Bioorg. Med. Chem. Lett. 17 (2007) 5868-5871
9. Morita H., Koyama K., Sugimoto Y., and Kobayashi J. Bioorg. Med. Chem. Lett. 15 (2005) 1051-1054
10. Suzuki H., Morita H., Shiro M., and Kobayashi J. Tetrahedron 60 (2004) 2489-2495
11. Suzuki H., Morita H., Iwasaki S., and Kobayashi J. Tetrahedron 59 (2003) 5307-5315
12. Kobayashi J., Suzuki H., Shimbo K., Takeya K., and Morita H. J. Org. Chem. 66 (2001) 6626-6633
13. Morita H., Shinbo T., Shigemori H., and Kobayashi J. Bioorg. Med. Chem. Lett. 10 (2000) 469-471
14. Kobayashi J., Hosoyama H., Wang X.-X., Shigemori H., Koiso Y., Iwasaki S., Sasaki T., Naito M., and Tsuruo T. Bioorg. Med. Chem. Lett. 7 (1997) 393-398
15. Asakawa Y., Toyota M., Hashimoto T., Tori M., Nagashima F., and Harinantenaina L. Heterocycles 76 (2008) 99-127
16. Harinantenaina L., Quang D.N., Takeshi N., Hashimoto T., Kohchi C., Soma G.I., and Asakawa Y. J. Nat. Prod. 68 (2005) 1779-1781
17. Asakawa Y., Toyota M., Tori M., and Hashimoto T. Spectroscopy 14 (2000) 149-175
18. Hashimoto T., Kanayama S., Fukuyama Y., Takaoke S., Tori M., and Asakawa Y. Tetrahedron Lett. 35 (1994) 911-912
19. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., and Still W.C. J. Comput. Chem. 11 (1990) 440-467
20. Halgren T. J. Am. Chem. Soc. 112 (1990) 4710-4723
21. Molecular modeling experiments employed Macromodel 9.1 equipped with the Maestro 7.5 graphical interface (Schrödinger, LLC, New York, NY, 2005) installed on a Linux Red Hat 9.0 system, and were performed using the MMFF force field.
22. Allerhand A., Doddrell D., and Komoroski R. J. Chem. Phys. 55 (1971) 189
23. Lyerla J.R., and Levy G.C. Topics in Carbon-13 NMR Spectroscopy 1 (1974) 79-148