Structure-activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 19, 1999, Pages 2875-2880

  Laurin, Patrick ^a   Ferroud, Didier ^a   Schio, Laurent ^a   Klich, Michael ^a   Dupuis Hamelin, Claudine ^b   Mauvais, Pascale ^b   Lassaigne, Patrice ^b   Bonnefoy, Alain ^b   Musicki, Branislav ^a  

^a Medicinal Chemistry   (France)

^b Infectious Disease Group   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); GYRASE INHIBITOR; NOVOBIOCIN;

AMINO ACID SUBSTITUTION; ARTICLE; DNA SUPERCOILING; DRUG INHIBITION; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; COUMARINS; DNA GYRASE; DNA TOPOISOMERASES, TYPE II; DNA, SUPERHELICAL; ENZYME INHIBITORS; ESCHERICHIA COLI; GRAM-POSITIVE BACTERIA; MOLECULAR STRUCTURE; NOVOBIOCIN; PEPTIDES, CYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

ESCHERICHIA COLI; NEGIBACTERIA;

EID: 0033523612     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00492-8     Document Type: Article

References (37)

1. 1. (a) Peng, H.; Marians, K. J. J. Biol. Chem. 1993, 268, 24481-24490. (b) Drlica, K.; Zhao, X. Microbiol. Mol. Biol. Rev. 1997, 61, 377-392. (c) Kidwai, M; Misra, P.; Kumar, R. Curr. Pharm. Des. 1998, 4, 101-118.
2. 1. (a) Peng, H.; Marians, K. J. J. Biol. Chem. 1993, 268, 24481-24490. (b) Drlica, K.; Zhao, X. Microbiol. Mol. Biol. Rev. 1997, 61, 377-392. (c) Kidwai, M; Misra, P.; Kumar, R. Curr. Pharm. Des. 1998, 4, 101-118.
3. 1. (a) Peng, H.; Marians, K. J. J. Biol. Chem. 1993, 268, 24481-24490. (b) Drlica, K.; Zhao, X. Microbiol. Mol. Biol. Rev. 1997, 61, 377-392. (c) Kidwai, M; Misra, P.; Kumar, R. Curr. Pharm. Des. 1998, 4, 101-118.
4. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
5. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
6. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
7. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
8. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
9. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
10. 2. (a) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (b) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1993, 60, 367-380. (c) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (d) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (e) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (f) Nakada, N.; Gmünder, H.; Hirata, T.; Arisawa, M. J. Biol. Chem. 1995, 270, 14286-14291; (g) Yamaji, K.; Masubuchi, M.; Kawahara, F.; Nakamura, Y.; Nishio, A.; Matsukuma, S.; Fujimori, M.; Nakada, N.; Watanabe, J.; Kamiyama, T. J. Antibiotics 1997, 50, 402-411.
11. 3. For the review on structure and mode of action of coumarins on DNA gyrase see: (a) Reece, R. J.; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375. (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43. (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
12. 3. For the review on structure and mode of action of coumarins on DNA gyrase see: (a) Reece, R. J.; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375. (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43. (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
13. 3. For the review on structure and mode of action of coumarins on DNA gyrase see: (a) Reece, R. J.; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375. (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43. (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
14. 3. For the review on structure and mode of action of coumarins on DNA gyrase see: (a) Reece, R. J.; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375. (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43. (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18. (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
15. 4. von Rosenstie, N.; Adam, D. Drugs 1994, 47, 872-901. (b) Hooper, D. C. Drugs 1995, 49 (Suppl. 2), 10-15.
16. 4. von Rosenstie, N.; Adam, D. Drugs 1994, 47, 872-901. (b) Hooper, D. C. Drugs 1995, 49 (Suppl. 2), 10-15.
17. 5. Sung, S. C. Biochim. Biophys. Acta. 1974, 361, 115-117. (b) Dephilip, R. M.; Lynch, W. E.; Liberman, I. Cancer Res. 1977, 37, 702-704. (c) Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707; (d) Castora, F. J.; Vissering, F. F.; Simpson, M. V. Biochim. Biophys. Acta. 1983, 740, 417-427. (e) Downes, C. S.; Ord, M. J.; Mullinger, A. M.; Collins, A. R. S.; Johnson, R. T. Carcinogenesis 1985, 6, 1343-1352.
18. 5. Sung, S. C. Biochim. Biophys. Acta. 1974, 361, 115-117. (b) Dephilip, R. M.; Lynch, W. E.; Liberman, I. Cancer Res. 1977, 37, 702-704. (c) Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707; (d) Castora, F. J.; Vissering, F. F.; Simpson, M. V. Biochim. Biophys. Acta. 1983, 740, 417-427. (e) Downes, C. S.; Ord, M. J.; Mullinger, A. M.; Collins, A. R. S.; Johnson, R. T. Carcinogenesis 1985, 6, 1343-1352.
19. 5. Sung, S. C. Biochim. Biophys. Acta. 1974, 361, 115-117. (b) Dephilip, R. M.; Lynch, W. E.; Liberman, I. Cancer Res. 1977, 37, 702-704. (c) Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707; (d) Castora, F. J.; Vissering, F. F.; Simpson, M. V. Biochim. Biophys. Acta. 1983, 740, 417-427. (e) Downes, C. S.; Ord, M. J.; Mullinger, A. M.; Collins, A. R. S.; Johnson, R. T. Carcinogenesis 1985, 6, 1343-1352.
20. 5. Sung, S. C. Biochim. Biophys. Acta. 1974, 361, 115-117. (b) Dephilip, R. M.; Lynch, W. E.; Liberman, I. Cancer Res. 1977, 37, 702-704. (c) Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707; (d) Castora, F. J.; Vissering, F. F.; Simpson, M. V. Biochim. Biophys. Acta. 1983, 740, 417-427. (e) Downes, C. S.; Ord, M. J.; Mullinger, A. M.; Collins, A. R. S.; Johnson, R. T. Carcinogenesis 1985, 6, 1343-1352.
21. 5. Sung, S. C. Biochim. Biophys. Acta. 1974, 361, 115-117. (b) Dephilip, R. M.; Lynch, W. E.; Liberman, I. Cancer Res. 1977, 37, 702-704. (c) Liu, L. F.; Liu, C. C.; Alberts, B. M. Cell 1980, 19, 697-707; (d) Castora, F. J.; Vissering, F. F.; Simpson, M. V. Biochim. Biophys. Acta. 1983, 740, 417-427. (e) Downes, C. S.; Ord, M. J.; Mullinger, A. M.; Collins, A. R. S.; Johnson, R. T. Carcinogenesis 1985, 6, 1343-1352.
22. 6. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624-629. (b) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Maxwell, A.; Skarzynsky, T.; Wonacott, A. J.; Wigley, D. B. J. Mol. Biol. 1994, 241, 128-130. (c) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420. (d) Tsai, F. T. F.; Singh, O. M. P.; Skarzynski, T.; Wonacott, J. A.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins: Struct. Funct. and Genet. 1997, 28, 41-52.
23. 6. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624-629. (b) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Maxwell, A.; Skarzynsky, T.; Wonacott, A. J.; Wigley, D. B. J. Mol. Biol. 1994, 241, 128-130. (c) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420. (d) Tsai, F. T. F.; Singh, O. M. P.; Skarzynski, T.; Wonacott, J. A.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins: Struct. Funct. and Genet. 1997, 28, 41-52.
24. 6. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624-629. (b) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Maxwell, A.; Skarzynsky, T.; Wonacott, A. J.; Wigley, D. B. J. Mol. Biol. 1994, 241, 128-130. (c) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420. (d) Tsai, F. T. F.; Singh, O. M. P.; Skarzynski, T.; Wonacott, J. A.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins: Struct. Funct. and Genet. 1997, 28, 41-52.
25. 6. (a) Wigley, D. B.; Davies, G. J.; Dodson, E. J.; Maxwell, A.; Dodson, G. Nature 1991, 351, 624-629. (b) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Maxwell, A.; Skarzynsky, T.; Wonacott, A. J.; Wigley, D. B. J. Mol. Biol. 1994, 241, 128-130. (c) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420. (d) Tsai, F. T. F.; Singh, O. M. P.; Skarzynski, T.; Wonacott, J. A.; Weston, S.; Tucker, A.; Pauptit, R. A.; Breeze, A.; Poyser, J. P.; O'Brien, R.; Ladbury, J. E.; Wigley, D. B. Proteins: Struct. Funct. and Genet. 1997, 28, 41-52.
26. 7. We successfully solved X-ray crystal structures of several coumarin derivatives with 24 kDa N-terminal fragment of gyrase B in collaboration with P. Oudet and D. Moras at the University of Louis Pasteur, Illkirch, France, unpublished results.
27. 8. (a) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (b) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. ( c) Poyser, J. P.; Telford, B.; Timms, D.; Block, M. H.; Hales, N. J. WO 9901442, 1999; Chem. Abstr. 1999, 130, 125099. (d) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2079-2084.
28. 8. (a) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (b) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. ( c) Poyser, J. P.; Telford, B.; Timms, D.; Block, M. H.; Hales, N. J. WO 9901442, 1999; Chem. Abstr. 1999, 130, 125099. (d) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2079-2084.
29. 8. (a) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (b) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. ( c) Poyser, J. P.; Telford, B.; Timms, D.; Block, M. H.; Hales, N. J. WO 9901442, 1999; Chem. Abstr. 1999, 130, 125099. (d) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2079-2084.
30. 8. (a) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (b) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. ( c) Poyser, J. P.; Telford, B.; Timms, D.; Block, M. H.; Hales, N. J. WO 9901442, 1999; Chem. Abstr. 1999, 130, 125099. (d) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2079-2084.
31. 8. (a) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (b) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. ( c) Poyser, J. P.; Telford, B.; Timms, D.; Block, M. H.; Hales, N. J. WO 9901442, 1999; Chem. Abstr. 1999, 130, 125099. (d) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2079-2084.
32. 9. Sethna, S.; Phadke, R. In Organic Reactions; John Willey & Sons; New York, 1953; Vol 7, pp 1-58.
33. 10. Anhydride 9 was prepared from 5-methylpyrrole-2-carboxylic acid by self coupling in the presence of p-toluenesulfonyl chloride and triethylamine in acetone at rt. in 76% yield.
34. 11. Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344.
35. 11. Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344.
36. 12. Mitscher, L. A.; Devasthale, P.; Zavod, R. In Quinolone Antimicrobial Agents; Hooper, D. C.; Wolfson, J. S. Ed.; American Chemical Society for Microbiology: Washington D. C., 1993; pp 3-51.
37. 13. The pKa of the 4-OH of the coumarin part of novobiocin was determined as 4.3. Hoeksema, H.; Johnson, J. L.; Hinman, J. W. J. Am. Chem. Soc. 1955, 77, 6710-6711.