Antitumor studies. Part 3: Design, synthesis, antitumor activity, and molecular docking study of novel 2-methylthio-, 2-amino-, and 2-(N-substituted amino)-10-alkyl-2-deoxo-5-deazaflavins

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 19, 2007, Pages 6336-6352

  Ali, Hamed I ^a   Ashida, Noriyuki ^b   Nagamatsu, Tomohisa ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b YAMASA CORPORATION   (Japan)

Author keywords

5 Deazaflavin; Antitumor activity; AutoDock; Protein tyrosine kinase

Indexed keywords

2 DEOXO 2 METHYLTHIO 5 DEAZAFLAVIN DERIVATIVE; 2 METHYLTHIOPYRIMIDIN 4(3H) ONE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTARABINE; PYRIMIDINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG; VILSMEIER REAGENT;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROLYSIS; MOLECULAR DOCKING; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

AMINO ACIDS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BINDING SITES; CELL LINE, TUMOR; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; FLAVINS; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 2;

EID: 34547666800     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.06.058     Document Type: Article

References (30)

1. Ali H.I., Tomita K., Akaho E., Kambara H., Miura S., Hayakawa H., Ashida N., Kawashima Y., Yamagishi T., Ikeya H., Yoneda F., and Nagamatsu T. Biorg. Med. Chem. 15 (2007) 242
2. Sakuma Y., Nagamatsu T., and Yoneda F. J. Chem. Soc. Chem. Comm. (1975) 977
3. Sakuma Y., Matsumoto S., Nagamatsu T., and Yoneda F. Chem. Pharm. Bull. 24 (1976) 338
4. Nagamatsu T., Yamato H., Ono M., Takarada S., and Yoneda F. J. Chem. Soc. Perkin Trans 1. (1992) 2101
5. Nagamatsu T., Kuroda K., Mimura N., Yanada R., and Yoneda F. J. Chem. Soc. Perkin Trans 1. (1994) 1125
6. Nagamatsu T., Yamada H., and Shiromoto K. Heterocycles 63 (2004) 9
7. Kimachi T., Yoneda F., and Sasaki T. J. Heterocycl. Chem. 29 (1992) 763
8. Wilson J.M., Henderson G., Black F., Sutherland A., Ludwig R.L., Vousden K.H., and Robins D. J. Biorg. Med. Chem. 15 (2007) 77
9. Sarhan A.A.O., Hozien Z.A., and El-Sherief H.A.H. Biorg. Med. Chem. 9 (2001) 2993
10. Paul M.K., and Mukhopadhyay A.K. Int. J. Med. Sci. 1 (2004) 101
11. Wang R., Wang Y., and Lu S. J. Med. Chem. 46 (2003) 2287
12. Vaque M., Arola A., Aliagas C., and Pujadas G. Bioinformatics 22 (2006) 1803
13. Baker B.R., Joseph B.R., and Schaub R.E. J. Org. Chem. 19 (1954) 631
14. Israel M., Protopapa H.K., Schlein H.N., and Modest E.J. J. Med. Chem. 7 (1964) 5
15. Atri G., Gomarasca P., Resnati G., Tronoconi G., Scolastico C., and Sirtori C.R. J. Med. Chem. 27 (1984) 1621
16. Wheeler H.L., and Jamieson G.S. Am. Chem. J. 32 (1904) 342
17. Koppel H.C., Springer R.H., Robins R.K., and Cheng C.C. J. Org. Chem. 26 (1961) 793
18. Coppola G.M., and Schuster H.F. J. Heterocycl. Chem. 26 (1989) 957
19. Curran W.V., and Angier R.B. J. Org. Chem. 28 (1963) 2672
20. Hübsch W., and Pfleiderer W. Helv. Chim. Acta 71 (1988) 1379
21. Machida H., Sakata S., Kuninaka A., Yoshino H., Saneyoshi M., and Nakayama C. Antimicrob. Agents Chemother. 16 (1979) 158
22. Machida H., Sakata S., Kuninaka A., and Yoshino H. Antimicrob. Agents Chemother. 20 (1981) 47
23. Ali, H.I. Ph.D. thesis, Okayama University, 2007; Okayama, Japan.
24. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
25. Mol C.D., Dougan D.R., Schneider T.R., Skene R.J., Kraus M.L., Scheibe D.N., Snell G.P., Zou H., Sang B.C., and Wilson K.P. J. Biol. Chem. 279 (2004) 31655
26. Ayoagi T., Yanada R., Bessho K., Yoneda F., and Armarego W.L.F. J. Heterocycl. Chem. 28 (1991) 1537
27. Yoneda F., Sakuma Y., Mizumoto S., and Ito R. J. Chem. Soc. Perkin Trans 1. (1976) 1805
28. Miura S., Yoshimura Y., Endo M., Machida H., Matsuda A., Tanaka M., and Sasaki T. Cancer Lett. 129 (1998) 103
29. Taylor R., and Kennard O. J. Am. Chem. Soc. 104 (1982) 5063
30. Taylor R., and Kennard O. Acc. Chem. Res. 17 (1984) 320