How to cite this paper
Phatangare, K., Patil, A., Patil, V & Sekar, N. (2012). Synthesis, photophysical properties of novel fluorescent metal complexes from 3-(1,3-benzoxazol-2-yl)naphthalen-2-ol, and their antimicrobial activity.Current Chemistry Letters, 1(1), 47-58.
Refrences
1. Sato Y., Yamada M., Yoshida S., Soneda T., Ishikawa M., Nizato T., Suzuki K., and Konno F. (1998) Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut. J. Med. Chem., 41, 3015-3021.
2. Katz L., (1953) Antituberculous compounds. III. Benzothiazole and benzoxazole derivatives. J. Am. Chem. Soc., 75, 712-714.
3. Devinder K., Jacob M. R., Reynolds M. B., and Kerwin S. M. (2002) Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Biorg. Med. Chem., 10, 3997-4004.
4. Kobayashi J., Madono T., and Shigemori H. (1995) Nakijinol, a novel sesquiterpenoid containing a benzoxazole ring from an Okinawan sponge. Tetrahedron Lett., 36, 5589-5590.
5. Rodriguez A. D., Ramirez C., Rodriguez I. I., and Gonzalez E. (1999) Novel antimycobacterial benzoxazole alkaloids, from the west Indian sea whip Pseudopterogorgia elisabethae. Org. Lett., 1, 527-530.
6. Ertan T., Yildiz I., Tekiner-Gulbas B., Bolelli K., Temiz-Arpaci O., Yalcin I., Aki E., Ozkan S., and Kaynak F. (2009) Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents. Eur. J. Med. Chem., 44, 501-510.
7. Dunwell D. W., and Evans D. (1977) Synthesis and antiinflammatory activity of some 2-aryl-6-benzoxazoleacetic acid derivatives. J. Med. Chem., 20, 797-801.
8. White A. W., Curtin N. J., Eastman B. W., Golding B. T., Hostomsky Z., Kyle S., Li J., Maegley K. A., Skalitzky D. J., Webber S. E., Yu X. H., and Griffin R. J. (2004) Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors. Bioorg. Med. Chem. Lett., 14, 2433-2437.
9. Hong S.-Y., Chung K.-H., You H.-J., Choi I. H., Chae M. J., Han J.-Y., Jung O.-K., Kang S.-J., and Ryu C.-K. (2004) Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation. Bioorg. Med. Chem. Lett., 14, 3563-3566.
10. Sakio S., Miyaoka S., Kaneko S., Fujii T., and Takai T. (2001) Electrophotographic photoreceptor. JP125,292.
11. Shi S.Q. (2000) Organometallic compexes with built-in fluorescent dyes for use in light emitting devices. TW 401,453.
12. Nakamura N., and Miyairi K. (1997) Organic EL device. EP 0,801,518.
13. Ogawa A. K., Abou-Zied O. K., Tsui V., Jimenez R., Case R. A., and Romesberg F. E. (2000) A Phototautomerizable model DNA base Pair. J. Am. Chem. Soc., 122, 9917-9920.
14. Reynolds M. B., DeLuca M. R. and Kerwin S. M. (1999) The novel Bis(benzoxazole) cytotoxic natural product UK-1 is a magnesium ion-dependent DNA binding agent and inhibitor of human Topoisomerase II. Bioorg. Chem., 27, 326-337.
15. Tong Y. P., Zheng S. L., and Chen X. M. (2005) Syntheses, structures, photoluminescence, and theoretical studies of a class of Beryllium (II) compounds of aromatic N, O-chelate ligands. Inorg Chem., 44, 4270-4275.
16. Wu H.-Y., Li H., Zhu B.-L., Wang S.-R., Zhang S.-M., Wu S.-H., and Huang W.-P. (2008) The synthesis and crystal structures of new 2-aminomethylbenzimidazole Zinc (II) complexes exhibiting luminescence. Trans Met. Chem., 33, 9-15.
17. Costa S. P. G., Oliveira E., Lodeiro C., and Raposo M. M. M. (2007) Synthesis, characterization and metal ion detection of novel fluoroionophores based on heterocyclic substituted alanines. Sensors, 7, 2096-2114.
18. Tanaka K., Kumagai T., Aoki h., Deguchi M., and Iwata S. (2001) Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cation. J. Org. Chem., 66, 7328-7333.
19. Zhang X.-B., Peng j., He C.-L., Shen G.-L., and Yu R.-Q. (2006) A highly selective fluorescent sensor for Cu2+ based on 2-(2?-hydroxyphenyl)benzoxazole in a poly(vinyl chloride) matrix. Anal. Chim. Acta, 567, 189-195.
20. Gong Z.-L., Ge F., and Zhao B.-X. (2011) Novel pyrazoline-based selective fluorescent sensor for Zn2+ in aqueous media. Sensor. Actuat. B-Chem., 159,148-153.
21. Ohshima A., Momotake A., and Arai T. (2004) A new fluorescent metal sensor with two binding moieties. Tetrahedron Lett., 45, 9377-9381.
22. Jiang J., Tang X., Dou W., Zhang H., Liu W., Wang C., and Zheng J. (2010) Synthesis and characterization of the ligand based on benzoxazole and its transition metal complexes: DNA-binding and antitumor activity. J. Inorg. Biochem., 104, 583-591.
23. McKee M. L., and Kerwin S. M. (2008) Synthesis, metal ion binding, and biological evaluation of new anticancer 2-(2?-hydroxyphenyl)benzoxazole analogs of UK-1. Bioorg. & Med. Chem., 16, 1775-1783.
24. Braun S., Botzki A., Salmen S., Textor C., Bernhardt B., Dove S., and Buschauer A. (2011) Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase. Eur. J. Med. Chem., 46, 9, 4419-4429.
25. Huang S.-T., Hsei I.-J., and Chen, C. (2006) Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorg. & Med. Chem., 14, 6106-6119.
26. Padalkar V. S., Patil V. S., Gupta V. D., Phatangare K. R., Umape P. G., and Sekar N. (2011) Synthesis, characterization, thermal properties and antimicrobial activities of 5-(diethylamino)-2-(5-nitro-1H-benzimidazol-2-yl)phenol and its transition metal complexes. ISRN Organic Chemistry, accepted for publication, doi:10.5402/2011/738361.
27. Ueno R.; Kitayama Y.; Minami K.; Wakamori H. (2004) Binaphthol derivative and process for producing the same. EP1380564 A1.
28. Padalkar V. S., Tathe A. B., Gupta V. D., Patil V. S., Phatangare K. R., and Sekar N. (2011) Synthesis and photo-physical characteristics of ESIPT inspired 2-Substituted benzimidazole, benzoxazole and benzothiazole fluorescent derivatives. J. Fluoresc., accepted for publication, doi: 10.1007/s10895-011-0962-8.
29. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. (2000) National Committee for Clinical Laboratory Standards, Wayne, PA.
30. Koeth L. M., King A., Knight M. J., Miller P. I., and Poupard J. A. (2000) Comparison of cation-adjusted Mueller–Hinton broth with Iso-Sensitest broth for the NCCLS broth microdilution method. J. Antimicrob. Chemother., 46, 369-376.
31. Sarker S. D., Nahar L., and Kumarasamy Y. (2007) Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods, 42, 321-324.
2. Katz L., (1953) Antituberculous compounds. III. Benzothiazole and benzoxazole derivatives. J. Am. Chem. Soc., 75, 712-714.
3. Devinder K., Jacob M. R., Reynolds M. B., and Kerwin S. M. (2002) Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Biorg. Med. Chem., 10, 3997-4004.
4. Kobayashi J., Madono T., and Shigemori H. (1995) Nakijinol, a novel sesquiterpenoid containing a benzoxazole ring from an Okinawan sponge. Tetrahedron Lett., 36, 5589-5590.
5. Rodriguez A. D., Ramirez C., Rodriguez I. I., and Gonzalez E. (1999) Novel antimycobacterial benzoxazole alkaloids, from the west Indian sea whip Pseudopterogorgia elisabethae. Org. Lett., 1, 527-530.
6. Ertan T., Yildiz I., Tekiner-Gulbas B., Bolelli K., Temiz-Arpaci O., Yalcin I., Aki E., Ozkan S., and Kaynak F. (2009) Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents. Eur. J. Med. Chem., 44, 501-510.
7. Dunwell D. W., and Evans D. (1977) Synthesis and antiinflammatory activity of some 2-aryl-6-benzoxazoleacetic acid derivatives. J. Med. Chem., 20, 797-801.
8. White A. W., Curtin N. J., Eastman B. W., Golding B. T., Hostomsky Z., Kyle S., Li J., Maegley K. A., Skalitzky D. J., Webber S. E., Yu X. H., and Griffin R. J. (2004) Potentiation of cytotoxic drug activity in human tumour cell lines, by amine-substituted 2-arylbenzimidazole-4-carboxamide PARP-1 inhibitors. Bioorg. Med. Chem. Lett., 14, 2433-2437.
9. Hong S.-Y., Chung K.-H., You H.-J., Choi I. H., Chae M. J., Han J.-Y., Jung O.-K., Kang S.-J., and Ryu C.-K. (2004) Synthesis and biological evaluation of benzimidazole-4,7-diones that inhibit vascular smooth muscle cell proliferation. Bioorg. Med. Chem. Lett., 14, 3563-3566.
10. Sakio S., Miyaoka S., Kaneko S., Fujii T., and Takai T. (2001) Electrophotographic photoreceptor. JP125,292.
11. Shi S.Q. (2000) Organometallic compexes with built-in fluorescent dyes for use in light emitting devices. TW 401,453.
12. Nakamura N., and Miyairi K. (1997) Organic EL device. EP 0,801,518.
13. Ogawa A. K., Abou-Zied O. K., Tsui V., Jimenez R., Case R. A., and Romesberg F. E. (2000) A Phototautomerizable model DNA base Pair. J. Am. Chem. Soc., 122, 9917-9920.
14. Reynolds M. B., DeLuca M. R. and Kerwin S. M. (1999) The novel Bis(benzoxazole) cytotoxic natural product UK-1 is a magnesium ion-dependent DNA binding agent and inhibitor of human Topoisomerase II. Bioorg. Chem., 27, 326-337.
15. Tong Y. P., Zheng S. L., and Chen X. M. (2005) Syntheses, structures, photoluminescence, and theoretical studies of a class of Beryllium (II) compounds of aromatic N, O-chelate ligands. Inorg Chem., 44, 4270-4275.
16. Wu H.-Y., Li H., Zhu B.-L., Wang S.-R., Zhang S.-M., Wu S.-H., and Huang W.-P. (2008) The synthesis and crystal structures of new 2-aminomethylbenzimidazole Zinc (II) complexes exhibiting luminescence. Trans Met. Chem., 33, 9-15.
17. Costa S. P. G., Oliveira E., Lodeiro C., and Raposo M. M. M. (2007) Synthesis, characterization and metal ion detection of novel fluoroionophores based on heterocyclic substituted alanines. Sensors, 7, 2096-2114.
18. Tanaka K., Kumagai T., Aoki h., Deguchi M., and Iwata S. (2001) Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cation. J. Org. Chem., 66, 7328-7333.
19. Zhang X.-B., Peng j., He C.-L., Shen G.-L., and Yu R.-Q. (2006) A highly selective fluorescent sensor for Cu2+ based on 2-(2?-hydroxyphenyl)benzoxazole in a poly(vinyl chloride) matrix. Anal. Chim. Acta, 567, 189-195.
20. Gong Z.-L., Ge F., and Zhao B.-X. (2011) Novel pyrazoline-based selective fluorescent sensor for Zn2+ in aqueous media. Sensor. Actuat. B-Chem., 159,148-153.
21. Ohshima A., Momotake A., and Arai T. (2004) A new fluorescent metal sensor with two binding moieties. Tetrahedron Lett., 45, 9377-9381.
22. Jiang J., Tang X., Dou W., Zhang H., Liu W., Wang C., and Zheng J. (2010) Synthesis and characterization of the ligand based on benzoxazole and its transition metal complexes: DNA-binding and antitumor activity. J. Inorg. Biochem., 104, 583-591.
23. McKee M. L., and Kerwin S. M. (2008) Synthesis, metal ion binding, and biological evaluation of new anticancer 2-(2?-hydroxyphenyl)benzoxazole analogs of UK-1. Bioorg. & Med. Chem., 16, 1775-1783.
24. Braun S., Botzki A., Salmen S., Textor C., Bernhardt B., Dove S., and Buschauer A. (2011) Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase. Eur. J. Med. Chem., 46, 9, 4419-4429.
25. Huang S.-T., Hsei I.-J., and Chen, C. (2006) Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorg. & Med. Chem., 14, 6106-6119.
26. Padalkar V. S., Patil V. S., Gupta V. D., Phatangare K. R., Umape P. G., and Sekar N. (2011) Synthesis, characterization, thermal properties and antimicrobial activities of 5-(diethylamino)-2-(5-nitro-1H-benzimidazol-2-yl)phenol and its transition metal complexes. ISRN Organic Chemistry, accepted for publication, doi:10.5402/2011/738361.
27. Ueno R.; Kitayama Y.; Minami K.; Wakamori H. (2004) Binaphthol derivative and process for producing the same. EP1380564 A1.
28. Padalkar V. S., Tathe A. B., Gupta V. D., Patil V. S., Phatangare K. R., and Sekar N. (2011) Synthesis and photo-physical characteristics of ESIPT inspired 2-Substituted benzimidazole, benzoxazole and benzothiazole fluorescent derivatives. J. Fluoresc., accepted for publication, doi: 10.1007/s10895-011-0962-8.
29. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. (2000) National Committee for Clinical Laboratory Standards, Wayne, PA.
30. Koeth L. M., King A., Knight M. J., Miller P. I., and Poupard J. A. (2000) Comparison of cation-adjusted Mueller–Hinton broth with Iso-Sensitest broth for the NCCLS broth microdilution method. J. Antimicrob. Chemother., 46, 369-376.
31. Sarker S. D., Nahar L., and Kumarasamy Y. (2007) Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods, 42, 321-324.