Reaction of the antitumor antibiotic olivomycin I with aryl diazonium salts. Synthesis, cytotoxic and antiretroviral potency of 5-aryldiazenyl-6-O-deglycosyl derivatives of olivomycin I

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 14, 2009, Pages 4961-4967

  Tevyashova, Anna N ^a   Olsufyeva, Eugenia N ^a   Turchin, Konstantin F ^a   Balzarini, Jan ^b   Bykov, Eugenyi E ^a   Dezhenkova, Lyubov G ^a   Shtil, Alexander A ^c   Preobrazhenskaya, Maria N ^a  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c N N BLOKHIN RUSSIAN CANCER RESEARCH CENTER   (Russian Federation)

Author keywords

Antiretroviral activity; Antitumor antibiotic; Arylazo coupling reaction; Olivomycin I

Indexed keywords

DIAZONIUM COMPOUND; OLIVOMYCIN; OLIVOMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; BORIC ACIDS; CELL LINE, TUMOR; CELL PROLIFERATION; DIAZONIUM COMPOUNDS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; OLIVOMYCINS; VIRUSES;

EID: 67650077275     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.076     Document Type: Article

References (19)

1. Lombo F., Menendez N., Salas J.A., and Mendez C. Appl. Microbiol. Biotechnol. 73 (2006) 1
2. Berlin Y.A., Kiseleva O.A., Kolosov M.N., Shemyakin M.M., Soifer V.S., Vasina I.V., and Yartseva I.V. Nature 218 (1968) 193
3. Simonova V.S., Samusenko A.V., Filippova N.A., Tevyashova A.N., Lyniv L.S., Kulik G.I., Chekhun V.F., and Shtil A.A. Bull. Exp. Biol. Med. 139 (2005) 455
4. Remsing L.L., Gonzalez A.M., Nur-e-Alam M., Fernandez-Lozano M.J., Brana A.F., Rix U., Oliveira M.A., Mendez C., Salas J.A., and Rohr J. J. Am. Chem. Soc. 125 (2003) 5745
5. Remsing L.L., Garcia-Bernardo J., Gonzalez A., Kuzel E., Rix U., Brana A.F., Bearden D.W., Mendez C., Salas J.A., and Rohr J. J. Am. Chem. Soc. 124 (2002) 1601
6. Kumar V., and Remers W.A. J. Med. Chem. 23 (1980) 376
7. Tevyashova A.N., Olsufyeva E.N., Balzarini J., Shtil A.A., Dezhenkova L.G., Bukhman V.M., Zbarsky V.B., and Preobrazhenskaya M.N. J. Antibiot. 63 (2009) 37
8. Thiem J., and Meyer B. Tetrahedron 37 (1981) 551
9. Yoshimura, Y.; Koenuma, M.; Matsumoto, K.; Tori, K.; Terui, Y. J. Antibiot., 1988, XLI, 53.
10. Brito-Arias M. Hydrolysis of Glycosides in Book: Synthesis and Characterization of Glycosides (2007), Springer, US
11. Hou M.H., Lu W.J., Lin H.Y., and Yuann J.M. Biochemistry 47 (2008) 5493
12. Menendez N., Nur-E-Alam M., Fischer C., Brana A.F., Salas J.A., Rohr J., and Mendez C. Appl. Environ. Microbiol. 72 (2006) 167
13. Keniry M.A., Owen E.A., and Shafer R.H. Biopolymers 54 (2000) 104
14. Hou M.H., Robinson H., Gao Y.G., and Wang A.H. Nucleic Acids Res. 32 (2004) 2214
15. Pindur U., Jansen M., and Lemster T. Curr. Med. Chem. 12 (2005) 2805
16. Pommier Y., and Marchand C. Curr. Med. Chem. Anticancer Agents 5 (2005) 421
17. Koelsch, F. C. Org. Synth. 1955, 3, 132.
18. Balzarini J., Pannecouque C., De Clercq E., Pavlov A.Y., Printsevskaya S.S., Miroshnikova O.V., Reznikova M.I., and Preobrazhenskaya M.N. J. Med. Chem. 46 (2003) 2755
19. Balzarini J., Keyaerts E., Vijgen H., De Clerq E., Ranst M.V., Printsevskaya S.S., Olsufyeva E.N., Solovieva S.E., and Preobrazhenskaya M.N. Antiviral Res. 72 (2006) 20