Synthesis and antibacterial study of 10, 15, 20-triphenyl-5-{4-hydroxy-3-(trimethylammonium)methyl}phenylporphyrin as models for combination of porphyrin and alkylating agent

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 6, 2003, Pages 1097-1100

  Zhang, Jiangye ^a   Wu, Xiaojun ^a   Cao, Xiaoping ^c   Yang, Fan ^a   Wang, Jiangfeng ^a   Zhou, Xiang ^a   Zhang, Xiao Lian ^b  

^a WUHAN UNIVERSITY   (China)

^b WUHAN UNIVERSITY   (China)

^c LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

10,15,20 TRIPHENYL 5 [4 HYDROXY 3 (DIMETHYLAMINE)METHYL]PHENYLPORPHYRIN; 10,15,20 TRIPHENYL 5 [4 HYDROXY 3 (TRIMETHYLAMMONIUM)METHYL]PHENYLPORPHYRIN; 10,15,20 TRIPHENYL 5 [4 METHOXY 3 (TRIMETHYLAMMONIUM)METHYL]PHENYLPORPHYRIN; PORPHYRIN DERIVATIVE; QUINONE DERIVATIVE; SINGLET OXYGEN; UNCLASSIFIED DRUG; ZINC COMPLEX;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; INHIBITION KINETICS; NONHUMAN; PHOTODYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; STAPHYLOCOCCUS AUREUS;

EID: 0037463774     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00053-2     Document Type: Article

References (31)

1. (a) Peter M.G. Angew. Chem., Int. Ed. Engl. 28:1989;555.
2. (b) Myers J.K., Cohen J.D., Wildlanski T.S. J. Am. Chem. Soc. 117:1995;11049.
3. (c) Cabaret D., Adedrian S.A., Garcia Gonzales M.J., Pratt R.F., Wakselman M. J. Org. Chem. 64:1999;713.
4. (a) Bolton J., Pisha L.E., Zhang F., Qiu S. Chem. Res. Toxicol. 11:1998;1113.
5. (b) Wan P., Barker B., Diao L., Fischer M., Shi Y., Yang C. Can. J. Chem. 74:1996;465.
6. (a) Pande P., Shearer J., Yang J., Greenberg W.A., Rokita S.E. J. Am. Chem. Soc. 121:1999;6773.
7. (b) Nakatani K., Higashida N., Saito I. Tetrahedron Lett. 38:1997;5005.
8. (c) Zhou Q., Turnbull K.D. J. Org. Chem. 65:2000;2022.
9. Brousmiche D., Wan P. Chem. Commun. 1998;491.
10. Modica E., Zanaletti R., Freccero M., Mella M. J. Org. Chem. 66:2001;41.
11. Chiang Y., Kresge A.J., Zhu Y. J. Am. Chem. Soc. 123:2001;8089.
12. (a) Sternberg E.D., Dolphin D. Tetrahedron. 54:1998;4151.
13. (b) Dougherty T.J. J. Natl. Cancer Inst. 90:1998;889.
14. (c) Pandey, R. K.; Zheng, G. In Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: Boston, 2000, Vol 6, pp 157.
15. (d) Bonnett R., Martinez G. Tetrahedron. 57:2001;9513.
16. (a) Villanueva A., Jori G. Cancer Lett. 73:1993;59.
17. (b) Villanueva A., Caggiari L., Jori G., Milanesi C. J. Photochem. Photobiol. B. 23:1994;49.
18. O'Brien P.M., Sliskovic D.R., Blankley C.J., Roth B.D., Wilson M.W., Hamelehle K.L., Krause B.R., Stanfield R.L. J. Med. Chem. 37:1994;1810.
19. Groves J.T., Matsunage A. Bioorg. Med. Chem. Lett. 6:1996;1595.
20. Pandey R.K., Shiau F.-Y., Smith N.W., Dougherty T.J., Smith K.M. Tetrahedron. 36:1992;7591.
21. Kai S., Hiramitsu S., Suzuki M., Masaki Y. Bioorg. Med. Chem. Lett. 11:2001;363.
22. (a) Youngblood W.J., Gryko D.T., Lammi R.K., Bocian D.F., Holten D., Lindsey J.S. J. Org. Chem. 67:2002;2111.
23. (b) Zhou X., Tse M.K., Zhou Z., Mak T.C.W., Chan K.S. J. Org. Chem. 61:1996;3590.
24. Williams D.H., Fleming I. Spectroscopic Methods in Organic Chemistry. 3rd ed. 1980;McGraw-Hill Book Company, UK.
25. +-I] 702.3227, found 702.3217.
26. (a) Michelsen M., Kliesch H., Wohrle D. Photochem. Photobiol. 64:1996;694.
27. (b) Kochevar I.E., Redmond R.W. Methods Enzymol. 319:2000;20.
28. (c) Oda K., Ogura S., Okura I. J. Photochem. Photobiol., B. 59:2000;20.
29. Gillman I.G., Yezek J.M., Manderville R.A. Chem. Commun. 1998;647.
30. Nakatani K., Higashida N., Saito I. Tetrahedron Lett. 38:1997;5005.
31. Difco Bacto Trytone (16 g/L), Difco Bacto Yeast extract (10 g/L) and NaCl (5 g/L).