Synthesis and biological evaluation of coumarincarboxylic acids as inhibitors of gyrase B. L-rhamnose as an effective substitute for L-noviose

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 19, 1999, Pages 2881-2886

  Ferroud, Didier ^a   Collard, Jeannine ^a   Klich, Michel ^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

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

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOASSAY; CHEMICAL MODIFICATION; DNA SUPERCOILING; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CARBOXYLIC ACIDS; COUMARINS; DNA GYRASE; DNA TOPOISOMERASES, TYPE II; DNA, SUPERHELICAL; ENZYME INHIBITORS; ESCHERICHIA COLI; MOLECULAR STRUCTURE; NOVOBIOCIN; RHAMNOSE;

ESCHERICHIA COLI; NEGIBACTERIA;

EID: 0033523720     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00493-X     Document Type: Article

References (28)

1. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
2. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
3. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
4. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
5. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
6. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g)Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
7. 1. For the recent work on novobiocin-like inhibitors of DNA gyrase see: (a) Ueda, Y.; Chuang, J. M; Crast, L. B. Jr.; Partyka, R. A. J. Antibiotics 1989, 42, 1379-1392. (b) Ueda, Y.; Chuang, J. M.; Fung-Tomc, J; Partyka, R. A. Bioorg. Med. Chem. Lett. 1994, 4, 1623-1628. (c) Bell, W.; Block, M. H.; Cook, C.; Grant, A.; Timms, D. J. Chem. Soc., Perkin Trans. 1997, 1, 2789-2801. (d) Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634. (e) Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344. (f) Laurin, P; Ferroud, D.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079-2084. (g) Laurin, P; Ferroud, D.; Schio, L.; Klich, M; Dupuis-Haelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med Chem. Lett. 1999, 9, 2875.
8. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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.
12. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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.
13. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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.
14. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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.
15. 2. For the family of cyclothialidine inhibitors of DNA gyrase see: (a) Arisawa, M.; Gotsshi, E. Kamiyama, T.; Masciadri, R.; Shimada, H.; Watanabe, J.; Hebeisen, P.; Link, H. WO 9218490, 1992; Chem. Abstr. 1992, 119, 117285; (b) Nakada, N.; Shimada, H.; Hirata, T.; Aoki, Y.; Kamiyama, J.; Watanabe, J.; Arisawa, M. Antimicrob. Agents Chemother. 1993, 37, 2656-2661. (c) Goetschi, E.; Angehrn, P.; Gmünder, H; Hebeisen, P.; Link, H.; Masciadri, R.; Nielsen, J. Pharmacol. Ther., 1994, 60, 367. (d) Watanabe, J.; Nakada, N.; Sawaira, S.; Shimada, H.; Ohshima, S.; Kamayma. T.; Arisawa, M. J. Antibiot. 1994, 47, 32-36. (e) Kamiyama, T.; Schimma, N.; Ohtsuka, T; Nakayama, N.; Itezono, Y.; Nakada, N.; Watabane, J.; Yokose, K. J. Antibiot. 1994, 47, 37-45. (f) Nakada, N.; Gmünder, Hirata, T.; Arisawa, M. Antimicrob. Agents Chemother. 1994, 38, 1966-1973. (g) Goschi, E.; Hebeisen, P.; Link, H. Lubbers, T. EP 675122, 1995; Chem. Abstr. 1995, 124, 146213. (h) 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.
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