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Volumn 41, Issue 21, 1998, Pages 4080-4100

Synthesis and antibacterial activity of ketolides (6-O-methyl-3- oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and -susceptible respiratory pathogens

Author keywords

[No Author keywords available]

Indexed keywords

11,12 DIDEOXY 3 DESCLADINOSYL 6 O METHYL 3 OXO 12,11 (OXYCARBONYL(2 (3 (4 QUINOLINYL)PROPYL)HYDRAZONO))ERYTHROMYCIN; 3 O DESCLADINOSYL 6 O METHYL 3 OXOERYTHROMYCIN 9 O (3 PIPERIDINYL)OXIME; 6 O METHYL 3 OXOERYTHROMYCIN DERIVATIVE; A 66321; ANTIBIOTIC AGENT; AZITHROMYCIN; CLARITHROMYCIN; ERYTHROMYCIN; ERYTHROMYCIN DERIVATIVE; HMR 3004; MACROLIDE; NARBOMYCIN; PIKROMYCIN; ROXITHROMYCIN; UNCLASSIFIED DRUG;

EID: 15644366975     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980240d     Document Type: Article
Times cited : (219)

References (103)
  • 3
    • 0022552513 scopus 로고
    • The renaissance of erythromycin
    • (a) Malmborg, A.-S. The renaissance of erythromycin. J. Antimicrob. Chemother. 1986, 18, 293-299.
    • (1986) J. Antimicrob. Chemother. , vol.18 , pp. 293-299
    • Malmborg, A.-S.1
  • 5
    • 0015225196 scopus 로고
    • Acid Degradation of Erythromycin A and Erythromycin B
    • (a) Kurath, P.; Jones, P. H.; Egan, R. S.; Perun, T. J. Acid Degradation of Erythromycin A and Erythromycin B. Experentia 1971, 27, 362.
    • (1971) Experentia , vol.27 , pp. 362
    • Kurath, P.1    Jones, P.H.2    Egan, R.S.3    Perun, T.J.4
  • 6
    • 0015811357 scopus 로고
    • Chemical modifications of erythromycins I. 8,9-anhydro-6,9-hemiketal of erythromycin A
    • (b) Krowicki, K.; Zamojski, A. Chemical modifications of erythromycins I. 8,9-anhydro-6,9-hemiketal of erythromycin A. J. Antibiot. 1974, 26, 569-574.
    • (1974) J. Antibiot. , vol.26 , pp. 569-574
    • Krowicki, K.1    Zamojski, A.2
  • 7
    • 0022641835 scopus 로고
    • Antibacterial activity of roxithromycin: A laboratory evaluation
    • (a) Chantot, J.-F.; Bryskier, A.; Gase, J.-C. Antibacterial activity of roxithromycin: a laboratory evaluation. J. Antibiot. 1986, 39, 660-668.
    • (1986) J. Antibiot. , vol.39 , pp. 660-668
    • Chantot, J.-F.1    Bryskier, A.2    Gase, J.-C.3
  • 8
    • 0026021209 scopus 로고
    • New ether oxime of erythromycin A a structure activity relationship study
    • (b) Gasc, J. C.; Gouin d'Ambrières, S.; Lutz, A.; Chantot, J. F. New ether oxime of erythromycin A a structure activity relationship study. J. Antibiot. 1991, 44, 313-330.
    • (1991) J. Antibiot. , vol.44 , pp. 313-330
    • Gasc, J.C.1    Gouin D'Ambrières, S.2    Lutz, A.3    Chantot, J.F.4
  • 9
    • 0021329213 scopus 로고
    • Chemical modifications of erythromycins I. Synthesis and antibacterial activity of 6-O-methylerythromycin A
    • Morimoto, S.; Takahashi, Y.; Watanabe, Y.; Omura, S. Chemical modifications of erythromycins I. Synthesis and antibacterial activity of 6-O-methylerythromycin A. J. Antibiot. 1984, 37, 187-189.
    • (1984) J. Antibiot. , vol.37 , pp. 187-189
    • Morimoto, S.1    Takahashi, Y.2    Watanabe, Y.3    Omura, S.4
  • 11
    • 33847583368 scopus 로고
    • Clinical Epidemiology of Resistance to Macrolides
    • Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds.; Marcel Dekker: New York
    • (a) Acar, J. F.; Goldstein, F. W. Clinical Epidemiology of Resistance to Macrolides. In New Macrolides, Azalides, and Streptogramins in Clinical Practice; Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds.; Marcel Dekker: New York, 1995; pp 41-49.
    • (1995) New Macrolides, Azalides, and Streptogramins in Clinical Practice , pp. 41-49
    • Acar, J.F.1    Goldstein, F.W.2
  • 12
    • 0008932941 scopus 로고
    • Epidemiology of resistance to macrolide antibiotics
    • Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris
    • (b) Shah, P. M.; Bryskier, A. Epidemiology of resistance to macrolide antibiotics. In Macrolides: Chemistry, Pharmacology and Clinical Uses; Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris, 1993; pp 143-166.
    • (1993) Macrolides: Chemistry, Pharmacology and Clinical Uses , pp. 143-166
    • Shah, P.M.1    Bryskier, A.2
  • 13
    • 0026760182 scopus 로고
    • The Crisis in Antibiotic Resistance
    • (a) Neu, H. C. The Crisis in Antibiotic Resistance. Science 1992, 257, 1064-1073.
    • (1992) Science , vol.257 , pp. 1064-1073
    • Neu, H.C.1
  • 14
    • 0026702093 scopus 로고
    • Antimicrobial resistance in streptococcus pneumoniae: An overview
    • (b) Appelbaum, P. C. Antimicrobial resistance in streptococcus pneumoniae: an overview. Clin. Infect. Dis. 1992, 15, 77-83.
    • (1992) Clin. Infect. Dis. , vol.15 , pp. 77-83
    • Appelbaum, P.C.1
  • 15
    • 0027956204 scopus 로고
    • Managment of infections caused by antibiotic-resistant Streptococcus Pneumoniae
    • (c) Friedland, I. R.; McCracken, G. H. Managment of infections caused by antibiotic-resistant Streptococcus pneumoniae. N. Engl. J. Med. 1994, 331, 377-382.
    • (1994) N. Engl. J. Med. , vol.331 , pp. 377-382
    • Friedland, I.R.1    McCracken, G.H.2
  • 16
    • 0030179960 scopus 로고    scopus 로고
    • Alexender Project Collaborative Group, Antimicrobial resistance among lower respiratory tract isolates of Streptococcus pneumoniae: Results of a 1992-93 western europe and USA collaborative surveillance study
    • (d) Goldstein, F. W.; Acar, J. F. Alexender Project Collaborative Group, Antimicrobial resistance among lower respiratory tract isolates of Streptococcus pneumoniae: results of a 1992-93 western europe and USA collaborative surveillance study. J. Antimicrob. Chemother. 1998, 38, 71-84.
    • (1998) J. Antimicrob. Chemother. , vol.38 , pp. 71-84
    • Goldstein, F.W.1    Acar, J.F.2
  • 17
    • 0003110965 scopus 로고
    • Mechanism of action of the macrolide and streptogramin antibiotics
    • Bryskier, A. J., Butzler, J.-P., Neu, H.C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris
    • (a) Aumercier, M.; Le Goffic, F. Mechanism of action of the macrolide and streptogramin antibiotics. In Macrolides: Chemistry, Pharmacology and Clinical Uses; Bryskier, A. J., Butzler, J.-P., Neu, H.C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris, 1993; pp 115-123.
    • (1993) Macrolides: Chemistry, Pharmacology and Clinical Uses , pp. 115-123
    • Aumercier, M.1    Le Goffic, F.2
  • 18
    • 2142688768 scopus 로고
    • Mode of Action and Resistance Mechanisms of Macrolides
    • Omura, S., Ed.; Academic Press: Orlando
    • (b) Corcoran, J. W. Mode of Action and Resistance Mechanisms of Macrolides. In Macrolide Antibiotics, Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: Orlando, 1984; pp 232-255.
    • (1984) Macrolide Antibiotics, Chemistry, Biology, and Practice , pp. 232-255
    • Corcoran, J.W.1
  • 19
    • 15644378340 scopus 로고
    • Recognition sites for antibiotics in rRNA
    • Hill, W. E., Dahlberg, A., Garrett, R. A., Moore, P. B., Schlessinger, D., Waener, J. R., Eds.; ASM Publications
    • (c) Cundliffe, E. Recognition sites for antibiotics in rRNA. In The Ribosome; Hill, W. E., Dahlberg, A., Garrett, R. A., Moore, P. B., Schlessinger, D., Waener, J. R., Eds.; ASM Publications: 1990; pp 482-483.
    • (1990) The Ribosome , pp. 482-483
    • Cundliffe, E.1
  • 20
    • 0002901629 scopus 로고
    • Mechanisms of resistance to macrolides and functionally related antibiotics
    • Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris
    • (a) Leclerq, R.; Courvalin, P. Mechanisms of resistance to macrolides and functionally related antibiotics. In Macrolides: Chemistry, Pharmacology and Clinical Uses; Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris, 1993; pp 125-141.
    • (1993) Macrolides: Chemistry, Pharmacology and Clinical Uses , pp. 125-141
    • Leclerq, R.1    Courvalin, P.2
  • 21
    • 15644362730 scopus 로고
    • Resistance to Macrolides, Azalides, and Streptogramins
    • Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds.; Marcel Dekker: New York
    • (b) Leclerq, R.; Courvalin, P. Resistance to Macrolides, Azalides, and Streptogramins. In New Macrolides, Azalides, and Streptogramins in Clinical Practice; Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds.; Marcel Dekker: New York, 1995; pp 31-40.
    • (1995) New Macrolides, Azalides, and Streptogramins in Clinical Practice , pp. 31-40
    • Leclerq, R.1    Courvalin, P.2
  • 22
    • 0028963496 scopus 로고
    • Erythromycin resistance by ribosome modification
    • (c) Weisblum, B.; Erythromycin resistance by ribosome modification. Antimicrob. Agents Chemother. 1995, 39, 577-585.
    • (1995) Antimicrob. Agents Chemother. , vol.39 , pp. 577-585
    • Weisblum, B.1
  • 23
    • 0029849428 scopus 로고    scopus 로고
    • Streptococcus pneumoniae and Streptococcus pyogenes Resistant to Macrolides but Sensitive to Clindamycin: A Common Resistance Pattern Mediated by an Efflux System
    • (a) Sutcliffe, J.; Tait-Kamradt, A.; Wondrack, L. Streptococcus pneumoniae and Streptococcus pyogenes Resistant to Macrolides but Sensitive to Clindamycin: a Common Resistance Pattern Mediated by an Efflux System. Antimicrob. Agents Chemother. 1996, 40, 1817-1824.
    • (1996) Antimicrob. Agents Chemother. , vol.40 , pp. 1817-1824
    • Sutcliffe, J.1    Tait-Kamradt, A.2    Wondrack, L.3
  • 24
    • 0029986588 scopus 로고    scopus 로고
    • Clinical strain of Staphylococcus aureus inactivates and causes efflux of macrolides
    • (b) Wondrack, L.; Massa, M.; Yang, B. V.; Sutcliffe, J. Clinical strain of Staphylococcus aureus inactivates and causes efflux of macrolides. Antimicrob. Agents Chemother. 1996, 40, 992-998.
    • (1996) Antimicrob. Agents Chemother. , vol.40 , pp. 992-998
    • Wondrack, L.1    Massa, M.2    Yang, B.V.3    Sutcliffe, J.4
  • 25
    • 0029796373 scopus 로고    scopus 로고
    • New directions in Antibacterial Research
    • Chu, D. T. W.; Plattner, J. J.; Katz, L. New directions in Antibacterial Research. J. Med. Chem. 1996, 39, 3853-3874.
    • (1996) J. Med. Chem. , vol.39 , pp. 3853-3874
    • Chu, D.T.W.1    Plattner, J.J.2    Katz, L.3
  • 26
    • 0040304811 scopus 로고
    • Chemical Modification and Structure-Activity Relationship of Macrolides
    • Omura, S., Ed.; Academic Press: Orlando
    • (a) Sakakibara, H.; Omura, S. Chemical Modification and Structure-Activity Relationship of Macrolides. In Macrolide Antibiotics, Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: Orlando, 1984; pp 85-119.
    • (1984) Macrolide Antibiotics, Chemistry, Biology, and Practice , pp. 85-119
    • Sakakibara, H.1    Omura, S.2
  • 27
    • 0038143816 scopus 로고
    • Structure-activity relationship of macrolides
    • Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris
    • (b) Gase, J.-C.; Bryskier, A. Structure-activity relationship of macrolides. In Macrolides: Chemistry, Pharmacology and Clinical Uses; Bryskier, A. J., Butzler, J.-P., Neu, H. C., Tulkens, P. M., Eds.; Arnette Blackwell: Paris, 1993; pp 67-82.
    • (1993) Macrolides: Chemistry, Pharmacology and Clinical Uses , pp. 67-82
    • Gase, J.-C.1    Bryskier, A.2
  • 28
    • 0002493783 scopus 로고
    • New Insights into the Structure-Activity Relationship of Macrolides and Azalides
    • Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds,; Marcel Dekker: New York
    • (c) Bryskier, A.; Agouridas, C.; Chantot, J.-F. New Insights into the Structure-Activity Relationship of Macrolides and Azalides. In New Macrolides, Azalides, and Streptogramins in Clinical Practice; Neu, H. C., Young, L. S., Zinner, S. H., Acar, J. F., Eds,; Marcel Dekker: New York, 1995; pp 3-30.
    • (1995) New Macrolides, Azalides, and Streptogramins in Clinical Practice , pp. 3-30
    • Bryskier, A.1    Agouridas, C.2    Chantot, J.-F.3
  • 29
    • 0031984970 scopus 로고    scopus 로고
    • Recent developments with macrolide antibiotics
    • (d) Kirst, H. A. Recent developments with macrolide antibiotics. Exp. Opin. Ther. Patents 1998, 8, 111-120.
    • (1998) Exp. Opin. Ther. Patents , vol.8 , pp. 111-120
    • Kirst, H.A.1
  • 30
    • 0017684039 scopus 로고
    • Macrolide resistance in Staphylococcus aureus: Inducers of macrolide resistance
    • Allen, N. Macrolide resistance in Staphylococcus aureus: inducers of macrolide resistance. Antimicrob. Agents Chemother. 1977, 11, 669-674.
    • (1977) Antimicrob. Agents Chemother. , vol.11 , pp. 669-674
    • Allen, N.1
  • 31
    • 84924648049 scopus 로고
    • The Synthesis of New Erythromycins
    • (a) Clark, R. K.; Freifelder, M. The Synthesis of New Erythromycins. Antibiot. Chemother. 1957, 7, 483-486.
    • (1957) Antibiot. Chemother. , vol.7 , pp. 483-486
    • Clark, R.K.1    Freifelder, M.2
  • 32
    • 0014651210 scopus 로고
    • Chemical Modifications of Erythromycin Antibiotics II. Synthesis of 4′-Hydroxyerythromycin A
    • (b) Jones, P. H.; Iyer, K. S.; Grundy, W. E. Chemical Modifications of Erythromycin Antibiotics II. Synthesis of 4′-Hydroxyerythromycin A. Antimicrob. Agents Chemother. 1969, 123-130.
    • (1969) Antimicrob. Agents Chemother. , pp. 123-130
    • Jones, P.H.1    Iyer, K.S.2    Grundy, W.E.3
  • 39
    • 0027243664 scopus 로고
    • The synthesis of novel 8a-aza-erythromycin derivatives via the Beckmann rearrangement of (9Z)-erythromycin A oxime
    • (b) Wilkening, R. R.; Ratcliffe, R. W.; Doss, G. A.; Bartizal, K. F.; Graham, A. C.; Herbert, C. M. The synthesis of novel 8a-aza-erythromycin derivatives via the Beckmann rearrangement of (9Z)-erythromycin A oxime. Bioorg. Med. Chem. Lett. 1993, 3, 1287-1292.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1287-1292
    • Wilkening, R.R.1    Ratcliffe, R.W.2    Doss, G.A.3    Bartizal, K.F.4    Graham, A.C.5    Herbert, C.M.6
  • 40
    • 0025233766 scopus 로고
    • Chemical modifications of erythromycins II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A
    • Morimoto, S.; Misawa, Y.; Adachi, T.; Nagate, T.; Watanabe, Y.; Omura, S. Chemical modifications of erythromycins II. Synthesis and antibacterial activity of O-alkyl derivatives of erythromycin A. J. Antibiot. 1990, 43, 286-294.
    • (1990) J. Antibiot. , vol.43 , pp. 286-294
    • Morimoto, S.1    Misawa, Y.2    Adachi, T.3    Nagate, T.4    Watanabe, Y.5    Omura, S.6
  • 42
    • 0021051559 scopus 로고
    • New fluorinated erythromycins obtained by mutasynthesis
    • (b) Toscano, L.; Fiorielo, G. New fluorinated erythromycins obtained by mutasynthesis. J. Antibiot. 1983, 36, 1439-1450.
    • (1983) J. Antibiot. , vol.36 , pp. 1439-1450
    • Toscano, L.1    Fiorielo, G.2
  • 45
    • 0027092577 scopus 로고
    • The in vitro profile of selected 14-membered azalides
    • (a) Jones, A. B.; Herbert, C. M. The in vitro profile of selected 14-membered azalides. J. Antibiot. 1992, 45, 1785-1791.
    • (1992) J. Antibiot. , vol.45 , pp. 1785-1791
    • Jones, A.B.1    Herbert, C.M.2
  • 46
    • 0026733824 scopus 로고
    • New Macrolides Antibiotics: Synthesis of a 14-Membered Azalide
    • (b) Jones, A. B. New Macrolides Antibiotics: Synthesis of a 14-Membered Azalide. J. Org. Chem. 1992, 57, 4361-4367.
    • (1992) J. Org. Chem. , vol.57 , pp. 4361-4367
    • Jones, A.B.1
  • 47
    • 0026340679 scopus 로고
    • Synthesis and antibacterial activities of C-21 functionalized derivatives of (9R)-9-amino-9-deoxoerythromycins A and B
    • (a) Lartey, P. A.; DeNinno, S. L.; Faghih, R.; Hardy, D. J.; Clement, J. J.; Plattner, J. J.; Stephens, R. L. Synthesis and antibacterial activities of C-21 functionalized derivatives of (9R)-9-amino-9-deoxoerythromycins A and B. J. Med. Chem. 1991, 34, 3390-3395.
    • (1991) J. Med. Chem. , vol.34 , pp. 3390-3395
    • Lartey, P.A.1    DeNinno, S.L.2    Faghih, R.3    Hardy, D.J.4    Clement, J.J.5    Plattner, J.J.6    Stephens, R.L.7
  • 48
    • 0023901653 scopus 로고
    • Modifications of macrolide antibiotics. Synthesis of 11-deoxy-11-(carboxyamino)-6-O-methylerythrornycin A 11,12-(cyclic esters) via intramolecular Michael reaction of O-carbamates with an α,β-unsaturated ketone
    • (a) Baker, W. R.; Clark, J. D.; Stephens, R. L.; Kim, K. H. Modifications of macrolide antibiotics. Synthesis of 11-deoxy-11-(carboxyamino)-6-O-methylerythrornycin A 11,12-(cyclic esters) via intramolecular Michael reaction of O-carbamates with an α,β-unsaturated ketone. J. Org. Chem. 1988, 53, 2340-2345.
    • (1988) J. Org. Chem. , vol.53 , pp. 2340-2345
    • Baker, W.R.1    Clark, J.D.2    Stephens, R.L.3    Kim, K.H.4
  • 49
    • 0024590644 scopus 로고
    • New macrolides active against streptococcus pyogenes with inducible or constitutive type of macrolidelincosamide-streptogramin B resistance
    • (b) Fernandes, P. B.; Baker, W. R.; Freiberg, L. A.; Hardy, D. J.; McDonald, E. J. New macrolides active against streptococcus pyogenes with inducible or constitutive type of macrolidelincosamide-streptogramin B resistance. Antimicrob. Agents Chemother. 1989, 33, 78-81.
    • (1989) Antimicrob. Agents Chemother. , vol.33 , pp. 78-81
    • Fernandes, P.B.1    Baker, W.R.2    Freiberg, L.A.3    Hardy, D.J.4    McDonald, E.J.5
  • 55
    • 0016224043 scopus 로고
    • Glycoside cleavage reactions on erythromycin A. Preparation of erythronolide A
    • (a) LeMahieu, R.; Carson, M.; Kierstead, R. W.; Fern, L. M.; Grunberg, D. E. Glycoside cleavage reactions on erythromycin A. Preparation of erythronolide A. J. Med. Chem. 1974, 17, 953-956.
    • (1974) J. Med. Chem. , vol.17 , pp. 953-956
    • LeMahieu, R.1    Carson, M.2    Kierstead, R.W.3    Fern, L.M.4    Grunberg, D.E.5
  • 58
    • 0003788982 scopus 로고
    • 14C]chloramphenicol binding to Escherichia coli. ribosomes by erythromycin derivatives
    • 14C]chloramphenicol binding to Escherichia coli. ribosomes by erythromycin derivatives. Antimicrob. Agents Chemother. 1974, 6, 39-45.
    • (1974) Antimicrob. Agents Chemother. , vol.6 , pp. 39-45
    • Pestka, S.1    LeMahieu, R.2
  • 60
    • 84981750002 scopus 로고
    • Pikromycin, ein bitter schmeckendes Antibioticum aus Actinomyceten
    • Brockmann, H.; Henkel, W. Pikromycin, ein bitter schmeckendes Antibioticum aus Actinomyceten. Chem. Ber. 1951, 84, 284-288.
    • (1951) Chem. Ber. , vol.84 , pp. 284-288
    • Brockmann, H.1    Henkel, W.2
  • 61
    • 36849026730 scopus 로고
    • Studies on compounds related to Auxin-a and Auxin-b. Part III
    • (a) Brown, J. B.; Henberst, H. B.; Jones, E. R. H. Studies on compounds related to Auxin-a and Auxin-b. Part III. J. Chem. Soc. 1950, 3634-3641.
    • (1950) J. Chem. Soc. , pp. 3634-3641
    • Brown, J.B.1    Henberst, H.B.2    Jones, E.R.H.3
  • 62
  • 63
    • 0023483280 scopus 로고
    • Roxithromycin: A pharmocokinetic review of a macrolide
    • Puri, S. K.; Lassman, H. B. Roxithromycin: a pharmocokinetic review of a macrolide. J. Antimicrob. Chemother. 1987, 20, 89-100.
    • (1987) J. Antimicrob. Chemother. , vol.20 , pp. 89-100
    • Puri, S.K.1    Lassman, H.B.2
  • 64
    • 33947487590 scopus 로고
    • Sulfoxide-Carbodiimide Reactions. I. A Facile Oxidation of Alcohols
    • Pfitzner, K. E.; Moffatt, J. G. Sulfoxide-Carbodiimide Reactions. I. A Facile Oxidation of Alcohols. J. Am. Chem. Soc. 1965, 87, 5661.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 5661
    • Pfitzner, K.E.1    Moffatt, J.G.2
  • 65
    • 84989040145 scopus 로고
    • Structural and Conformational Analysis of (E)-erythromycin A Oxime
    • McGill, J. M.; Johnson, R. Structural and Conformational Analysis of (E)-erythromycin A Oxime. Magn. Reson. Chem. 1993, 31, 273-277.
    • (1993) Magn. Reson. Chem. , vol.31 , pp. 273-277
    • McGill, J.M.1    Johnson, R.2
  • 66
    • 0001028784 scopus 로고
    • S-[ω-(aminooxy)alkyl]isothiuronium salts, ω,ω′-bis(aminooxy)alkanes and related compounds
    • Bauer, L.; Suresh, K. S. S-[ω-(aminooxy)alkyl]isothiuronium salts, ω,ω′-bis(aminooxy)alkanes and related compounds. J. Org. Chem. 1963, 28, 1604-1608.
    • (1963) J. Org. Chem. , vol.28 , pp. 1604-1608
    • Bauer, L.1    Suresh, K.S.2
  • 67
    • 15644380445 scopus 로고
    • A new reagent for the synthesis of N-monoalkylated hydroxyl-amines; N-tosyl-O-2,4,6-trimethylbenzylhydroxylamine
    • Isowa, Y.; Kurita, H. A new reagent for the synthesis of N-monoalkylated hydroxyl-amines; N-tosyl-O-2,4,6-trimethylbenzylhydroxylamine. Bull. Chem. Soc. Jpn. 1974, 47, 720-722.
    • (1974) Bull. Chem. Soc. Jpn. , vol.47 , pp. 720-722
    • Isowa, Y.1    Kurita, H.2
  • 68
    • 0020361036 scopus 로고
    • O-Sulfated β-Lactam Hydroxamic Acids (Monosulfactams). Novel Monocyclic β-Lactam Antibiotics of Synthetic Origin
    • Gordon, E. M.; Ondetti, M. A.; Pluscec, J.; Cimarusti, C. M.; Bonner, D. P.; Sykes, R. B. O-Sulfated β-Lactam Hydroxamic Acids (Monosulfactams). Novel Monocyclic β-Lactam Antibiotics of Synthetic Origin. J. Am. Chem. Soc. 1982, 104, 6053-6060.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 6053-6060
    • Gordon, E.M.1    Ondetti, M.A.2    Pluscec, J.3    Cimarusti, C.M.4    Bonner, D.P.5    Sykes, R.B.6
  • 69
    • 0003047929 scopus 로고
    • Contribution à l'étude des hydroxylamines O-substituées. (Contribution to the study of O-substituted hydroxylamines.)
    • Winternitz, F.; Lachazette, R. Contribution à l'étude des hydroxylamines O-substituées. (Contribution to the study of O-substituted hydroxylamines.) Bull. Soc. Chim. Fr. 1958, 664-667.
    • (1958) Bull. Soc. Chim. Fr. , pp. 664-667
    • Winternitz, F.1    Lachazette, R.2
  • 70
    • 0000172059 scopus 로고
    • Reactions of β-substituted amines IV
    • Hammer, C, F.; Weber, J. D. Reactions of β-substituted amines IV. Tetrahedron 1981, 37, 2173-2180.
    • (1981) Tetrahedron , vol.37 , pp. 2173-2180
    • Hammer, C.F.1    Weber, J.D.2
  • 71
    • 0025027166 scopus 로고
    • The biosynthesis of Sceletium alkaloids in Sceletium subvelutinium L. Bolus
    • Herbert, R. B.; Abdullah, E. The biosynthesis of Sceletium alkaloids in Sceletium subvelutinium L. Bolus. Tetrahedron 1990, 46, 7105-7118.
    • (1990) Tetrahedron , vol.46 , pp. 7105-7118
    • Herbert, R.B.1    Abdullah, E.2
  • 73
    • 85011124318 scopus 로고
    • Synthesis of (3-aminopropyl)guanidine derivatives
    • Ueda, T.; Ishizaki, K. Synthesis of (3-aminopropyl)guanidine derivatives. Chem. Pharm. Bull. 1967, 15, 228-232.
    • (1967) Chem. Pharm. Bull. , vol.15 , pp. 228-232
    • Ueda, T.1    Ishizaki, K.2
  • 74
    • 85023355171 scopus 로고
    • Selective reduction of azides. Improved preparation of α,α-disubstituted benzylamines
    • Balderman, D.; Kalir, A. Selective reduction of azides. Improved preparation of α,α-disubstituted benzylamines. Synthesis 1978, 24-26.
    • (1978) Synthesis , pp. 24-26
    • Balderman, D.1    Kalir, A.2
  • 75
    • 0013808475 scopus 로고
    • Azioni farmacologiche di nuovi derivati chimicamente correlati con la guanetidina
    • Pasini, C.; Coda, S.; Colo, V.; Ferrini, R.; Glässer, A. Azioni farmacologiche di nuovi derivati chimicamente correlati con la guanetidina. Farmaco Ed. Sci. 1965, 20, 673-685.
    • (1965) Farmaco Ed. Sci. , vol.20 , pp. 673-685
    • Pasini, C.1    Coda, S.2    Colo, V.3    Ferrini, R.4    Glässer, A.5
  • 76
    • 0342297460 scopus 로고
    • Ketolides, A New Distinct Semi-synthetic Class of Macrolides
    • Abstr. No. F-164
    • Previous works concerning the ketolides were presented during the following meetings and papers: (a) Agouridas, C.; Benedetti, Y.; Denis, A.; Fromentin, C.; Gouin d'Ambrieres, S.; Le Martret, O.; Chantot, J.-F. Ketolides, A New Distinct Semi-synthetic Class of Macrolides. 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1994; Abstr. No. F-164. (b) Agouridas, C.; Benedetti, Y.; Denis, A.; Le Martret, O.; Chantot, J.-F. Ketolides: A New Distinct Class of Macrolide Antibacterials. Synthesis and Structural Characteristics of RU 004. 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1995; Abstr. No. F-157.
    • (1994) 34th Interscience Conference on Antimicrobial Agents and Chemotherapy
    • Agouridas, C.1    Benedetti, Y.2    Denis, A.3    Fromentin, C.4    Gouin D'Ambrieres, S.5    Le Martret, O.6    Chantot, J.-F.7
  • 77
    • 0003259907 scopus 로고
    • Ketolides: A New Distinct Class of Macrolide Antibacterials. Synthesis and Structural Characteristics of RU 004
    • Abstr. No. F-157
    • Previous works concerning the ketolides were presented during the following meetings and papers: (a) Agouridas, C.; Benedetti, Y.; Denis, A.; Fromentin, C.; Gouin d'Ambrieres, S.; Le Martret, O.; Chantot, J.-F. Ketolides, A New Distinct Semi-synthetic Class of Macrolides. 34th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1994; Abstr. No. F-164. (b) Agouridas, C.; Benedetti, Y.; Denis, A.; Le Martret, O.; Chantot, J.-F. Ketolides: A New Distinct Class of Macrolide Antibacterials. Synthesis and Structural Characteristics of RU 004. 35th Interscience Conference on Antimicrobial Agents and Chemotherapy, 1995; Abstr. No. F-157.
    • (1995) 35th Interscience Conference on Antimicrobial Agents and Chemotherapy
    • Agouridas, C.1    Benedetti, Y.2    Denis, A.3    Le Martret, O.4    Chantot, J.-F.5
  • 83
    • 0030827227 scopus 로고    scopus 로고
    • Antibacterial Activity of RU 64004 (HMR 3004), a Novel Ketolide derivative Active Against Respiratory Pathogens
    • (a) Agouridas, C.; Bonnefoy, A.; Chantot, J.-F. Antibacterial Activity of RU 64004 (HMR 3004), a Novel Ketolide derivative Active Against Respiratory Pathogens. Antimicrob. Agents Chemother. 1997, 41, 2149-2158.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 2149-2158
    • Agouridas, C.1    Bonnefoy, A.2    Chantot, J.-F.3
  • 84
    • 0031053885 scopus 로고    scopus 로고
    • In Vitro Evaluation of a Novel Ketolide Antimicrobial Agent, RU 64004
    • (b) Jamjian, C.; Biedenbach, D. J.; Jones, R. N. In Vitro Evaluation of a Novel Ketolide Antimicrobial Agent, RU 64004. Antimicrob. Agents Chemother. 1997, 41, 454-459.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 454-459
    • Jamjian, C.1    Biedenbach, D.J.2    Jones, R.N.3
  • 85
    • 0030956596 scopus 로고    scopus 로고
    • Susceptibilities of 228 Penicillin and Erythromycin Susceptible and Resistant Pneumococci to RU 64004, a new Ketolide, Compared with Susceptibilities to 16 other Agents
    • (c) Ednie, L. M.; Spangler, S. K.; Jacobs, M. R.; Appelbaum, P. C. Susceptibilities of 228 Penicillin and Erythromycin Susceptible and Resistant Pneumococci to RU 64004, a new Ketolide, Compared with Susceptibilities to 16 other Agents. Antimicrob. Agents Chemother. 1997, 41, 1033-1036.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 1033-1036
    • Ednie, L.M.1    Spangler, S.K.2    Jacobs, M.R.3    Appelbaum, P.C.4
  • 95
    • 0002679069 scopus 로고
    • Procedures and theoretical considerations for testing antimicrobial agents in agar media
    • Lorian, V., Ed.; Williams and Wilkins: Baltimore, MD
    • (a) Barry, A. Procedures and theoretical considerations for testing antimicrobial agents in agar media. In Antibiotics in Laboratory Medicine; Lorian, V., Ed.; Williams and Wilkins: Baltimore, MD, 1991; pp 1-16.
    • (1991) Antibiotics in Laboratory Medicine , pp. 1-16
    • Barry, A.1
  • 96
    • 0001994881 scopus 로고
    • Susceptibility testing of antimicrobials in liquid media
    • Lorian, V., Ed.; Williams and Wilkins: Baltimore, MD
    • (b) Amsterdam, D. Susceptibility testing of antimicrobials in liquid media. In Antibiotics in Laboratory Medicine; Lorian, V., Ed.; Williams and Wilkins: Baltimore, MD, 1991; pp 53-105.
    • (1991) Antibiotics in Laboratory Medicine , pp. 53-105
    • Amsterdam, D.1
  • 97
    • 0002132354 scopus 로고
    • Evaluation of new antimicrobials in vitro and in experimental animal infections
    • Lorian, V., Ed.; Williams and Wilkins; Baltimore, MD
    • (c) Cleeland, R.; Squires, E. Evaluation of new antimicrobials in vitro and in experimental animal infections. In Antibiotics in Laboratory Medicine; Lorian, V., Ed.; Williams and Wilkins; Baltimore, MD, 1991; pp 739-786.
    • (1991) Antibiotics in Laboratory Medicine , pp. 739-786
    • Cleeland, R.1    Squires, E.2
  • 98
    • 84951384024 scopus 로고
    • A simplified method of evaluating dose-effect experiments
    • (d) Litchfield, J. T.; Wilcoxon, F. A simplified method of evaluating dose-effect experiments. J. Pharmacol. Exp. Ther. 1949, 96, 99-113.
    • (1949) J. Pharmacol. Exp. Ther. , vol.96 , pp. 99-113
    • Litchfield, J.T.1    Wilcoxon, F.2
  • 99
    • 0023634930 scopus 로고
    • Improved medium for antimicrobial susceptibility testing of Haemophilus influenzae
    • (e) Jorgensen, J. H.; Redding, J. S.; Maher. L. A.; Howell, A. W. Improved medium for antimicrobial susceptibility testing of Haemophilus influenzae. J. Clin. Microbiol. 1987, 25, 2105-2113.
    • (1987) J. Clin. Microbiol. , vol.25 , pp. 2105-2113
    • Jorgensen, J.H.1    Redding, J.S.2    Maher, L.A.3    Howell, A.W.4
  • 100
    • 0027245634 scopus 로고
    • pH-Metric log P. II: Reffinement of partition coefficients and ionization constants of multiprotic substances
    • (a) Avdeef, A. pH-Metric log P. II: Reffinement of partition coefficients and ionization constants of multiprotic substances. J. Pharrn. Sci. 1993, 82, 183-190.
    • (1993) J. Pharrn. Sci. , vol.82 , pp. 183-190
    • Avdeef, A.1
  • 101
    • 0027071736 scopus 로고
    • pH-Metric log P. I: Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances
    • (b) Avdeef, A. pH-Metric log P. I: Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances. Quant. Struct.-Act. Relat. 1992, 11, 510-517.
    • (1992) Quant. Struct.-Act. Relat. , vol.11 , pp. 510-517
    • Avdeef, A.1


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