메뉴 건너뛰기




Volumn 24, Issue 1, 2005, Pages 19-39

New carbohydrate derivatives of norfloxacin

Author keywords

Glycosylamine; Glycosylthiosemicarbazide; Glycosylthiourea; Glycosylurea; Norfloxacin

Indexed keywords


EID: 27844491140     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1081/CAR-200049410     Document Type: Article
Times cited : (6)

References (51)
  • 1
    • 0038750674 scopus 로고    scopus 로고
    • Glycosylation of 4-aryl-1-thioxo[1,2,4]-triazolo[4,3-a]quinazolin-5(4H)- one
    • (a) Saleh, M.A.; Abdel-Megeed, M.F. Glycosylation of 4-aryl-1-thioxo[1,2, 4]-triazolo[4,3-a]quinazolin-5(4H)-one. J. Carbohydr. Chem. 2003, 22, 79-94;
    • (2003) J. Carbohydr. Chem. , vol.22 , pp. 79-94
    • Saleh, M.A.1    Abdel-Megeed, M.F.2
  • 2
    • 0029564692 scopus 로고
    • Synthesis, conformational and configurational studies of some new acetylated glycosides of 2-thio-3-aryl-4(3H)-quinazolinones, their thiono and 3,1-benzothiazine-2,4-dithione
    • (b) Abdel-Megeed, M.F.; Saleh, M.A.; Aly, Y.A.; Abdo, I.M. Synthesis, conformational and configurational studies of some new acetylated glycosides of 2-thio-3-aryl-4(3H)-quinazolinones, their thiono and 3,1-benzothiazine-2,4- dithione. Nucleosides, Nucleotides Nucleic Acids 1995, 14, 1985-1996;
    • (1995) Nucleosides, Nucleotides Nucleic Acids , vol.14 , pp. 1985-1996
    • Abdel-Megeed, M.F.1    Saleh, M.A.2    Aly, Y.A.3    Abdo, I.M.4
  • 3
    • 0034753080 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of N-glycosides derived from 6-amino-3-aryl-2-methyl-4(3H)-quinazolinones
    • (c) Saleh, M.A.; Abbas, Y.A.; Abdel-Hai, F.E.; Youssef, S.A. Synthesis and antiviral evaluation of N-glycosides derived from 6-amino-3-aryl-2-methyl- 4(3H)-quinazolinones. Nucleosides, Nucleotides Nucleic Acids 2001, 20 (10&11), 1891-1902;
    • (2001) Nucleosides, Nucleotides Nucleic Acids , vol.20 , Issue.10-11 , pp. 1891-1902
    • Saleh, M.A.1    Abbas, Y.A.2    Abdel-Hai, F.E.3    Youssef, S.A.4
  • 4
    • 0036010563 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of some new glycosyl thioureas containing a quinazolinone nucleus
    • (d) Saleh, M.A.; Abdel-Megeed, M.F.; Abdo, M.A.; Shokr, A.M. Synthesis and antiviral evaluation of some new glycosyl thioureas containing a quinazolinone nucleus. Nucleosides, Nucleotides Nucleic Acids 2002, 21 (1), 93-106.
    • (2002) Nucleosides, Nucleotides Nucleic Acids , vol.21 , Issue.1 , pp. 93-106
    • Saleh, M.A.1    Abdel-Megeed, M.F.2    Abdo, M.A.3    Shokr, A.M.4
  • 5
    • 27844551399 scopus 로고
    • Quinoline carboxylic acid derivatives
    • Belg. Pat. 863,429, 16 May, 1978
    • (a) Irikura, T. Quinoline carboxylic acid derivatives. Belg. Pat. 863,429, 16 May, 1978 (Chem. Abstr. 1978, 89, 180050k);
    • (1978) Chem. Abstr. , vol.89
    • Irikura, T.1
  • 6
    • 4243194183 scopus 로고
    • 7-Dialkylamino-6-halo-4-oxo-1,4-dihydro-3-quinolinecarboxylic acids
    • Ger. Offen. 2,840,910, 5 April, 1979
    • (b) Pesson, M. 7-Dialkylamino-6-halo-4-oxo-1,4-dihydro-3- quinolinecarboxylic acids. Ger. Offen. 2,840,910, 5 April, 1979 (Chem. Abstr. 1979, 91, 20344x);
    • (1979) Chem. Abstr. , vol.91
    • Pesson, M.1
  • 7
    • 0019252702 scopus 로고
    • Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids
    • (c) Koga, H.; Itoh, A.; Murayama, S.; Suzue, S.; Irikura, T. Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. J. Med. Chem. 1980, 23, 1358-1363;
    • (1980) J. Med. Chem. , vol.23 , pp. 1358-1363
    • Koga, H.1    Itoh, A.2    Murayama, S.3    Suzue, S.4    Irikura, T.5
  • 8
  • 10
    • 0023130703 scopus 로고
    • Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]benzothiazine-6-carboxylic acids
    • (a) Cecchetti, V.; Fravolini, A.; Fringuelli, R.; Mascellani, G.; Pagella, P.; Palmioli, M.; Segre, G.; Terni, P. Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de] benzothiazine-6-carboxylic acids. J. Med. Chem. 1987, 30, 465-473;
    • (1987) J. Med. Chem. , vol.30 , pp. 465-473
    • Cecchetti, V.1    Fravolini, A.2    Fringuelli, R.3    Mascellani, G.4    Pagella, P.5    Palmioli, M.6    Segre, G.7    Terni, P.8
  • 11
    • 0024596116 scopus 로고
    • Studies on prodrugs. Synthesis and antimicrobial activity of N-[(4-methyl-5-methylene-2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin
    • (b) Kondo, H.; Sakamoto, F.; Uno, T.; Kawahata, Y.; Tsukamoto, G. Studies on prodrugs. Synthesis and antimicrobial activity of N-[(4-methyl-5-methylene- 2-oxo-1,3-dioxolan-4-yl)oxy]norfloxacin. J. Med. Chem. 1989, 32, 671-674;
    • (1989) J. Med. Chem. , vol.32 , pp. 671-674
    • Kondo, H.1    Sakamoto, F.2    Uno, T.3    Kawahata, Y.4    Tsukamoto, G.5
  • 13
    • 0025057986 scopus 로고
    • New quinolone antibacterial agents. Synthesis and biological activity of 7-(3,3- or 3,4-disubstituted-1-pyrrolidinyl)-quinoline-3-carboxylic acids
    • (d) Hagen, S.E.; Domagala, J.M.; Heifetz, C.L.; Sanchez, J.P.; Solomon, M. New quinolone antibacterial agents. Synthesis and biological activity of 7-(3,3- or 3,4-disubstituted-1-pyrrolidinyl)-quinoline-3-carboxylic acids. J. Med. Chem. 1990, 33, 849-854;
    • (1990) J. Med. Chem. , vol.33 , pp. 849-854
    • Hagen, S.E.1    Domagala, J.M.2    Heifetz, C.L.3    Sanchez, J.P.4    Solomon, M.5
  • 14
    • 0025050739 scopus 로고
    • Synthesis of antimicrobial agents. 3. Syntheses and antibacterial activities of 7-(4-hydroxypiperazin-1-yl)-quinolones
    • (e) Uno, T.; Kondo, H.; Inoue, Y.; Kawahata, Y.; Sotomura, M.; Iuchi, K.; Tsukamoto, G. Synthesis of antimicrobial agents. 3. Syntheses and antibacterial activities of 7-(4-hydroxypiperazin-1-yl)-quinolones. J. Med. Chem. 1990, 33, 2929-2932;
    • (1990) J. Med. Chem. , vol.33 , pp. 2929-2932
    • Uno, T.1    Kondo, H.2    Inoue, Y.3    Kawahata, Y.4    Sotomura, M.5    Iuchi, K.6    Tsukamoto, G.7
  • 15
    • 0026034731 scopus 로고
    • Fluoronaphthyridines and -quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1,1-dimethyl-2- fluoroethyl), 1-[1-methyl-1-(fluoromethyl)-2-fluoroethyl], and 1-[1,1-(difluoromethyl)-2-fluoroethyl] substituted derivatives
    • (f) Remuzon, P.; Bouzard, D.; Di Cesare, P.; Essiz, M.; Jacquet, J.P.; Kiechel, J.R.; Ledoussal, B.; Kessler, R.E.; Fung-Tomc, J. Fluoronaphthyridines and -quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1,1-dimethyl-2-fluoroethyl), 1-[1-methyl-1- (fluoromethyl)-2-fluoroethyl], and 1-[1,1-(difluoromethyl)-2-fluoroethyl] substituted derivatives. J. Med. Chem. 1991, 34, 29-37;
    • (1991) J. Med. Chem. , vol.34 , pp. 29-37
    • Remuzon, P.1    Bouzard, D.2    Di Cesare, P.3    Essiz, M.4    Jacquet, J.P.5    Kiechel, J.R.6    Ledoussal, B.7    Kessler, R.E.8    Fung-Tomc, J.9
  • 17
    • 0026100361 scopus 로고
    • 1-substituents of quinolone antibacterials
    • 1-substituents of quinolone antibacterials. J. Med. Chem. 1991, 34, 131-139;
    • (1991) J. Med. Chem. , vol.34 , pp. 131-139
    • Ohta, M.1    Koga, H.2
  • 18
    • 0026100364 scopus 로고
    • Synthesis, antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride
    • (i) Chu, D.T.W.; Nordeen, C.W.; Hardy, D.J.; Swanson, R.N.; Giardina, W.J.; Pernet, A.G.; Plattner, J.J. Synthesis, antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride. J. Med. Chem. 1991, 34, 168-174;
    • (1991) J. Med. Chem. , vol.34 , pp. 168-174
    • Chu, D.T.W.1    Nordeen, C.W.2    Hardy, D.J.3    Swanson, R.N.4    Giardina, W.J.5    Pernet, A.G.6    Plattner, J.J.7
  • 22
    • 0025726861 scopus 로고
    • Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6- fluoroquinoline-3-carboxylic acids
    • (m) Hagen, S.E.; Domagala, J.M.; Heifetz, C.L.; Johnson, J. Synthesis and biological activity of 5-alkyl-1,7,8-trisubstituted-6-fluoroquinoline-3- carboxylic acids. J. Med. Chem. 1991, 34, 1155-1161;
    • (1991) J. Med. Chem. , vol.34 , pp. 1155-1161
    • Hagen, S.E.1    Domagala, J.M.2    Heifetz, C.L.3    Johnson, J.4
  • 24
    • 0026507977 scopus 로고
    • The synthesis and biological activity of new 7-[2-(cyanomethyl) piperazinyl]- and 7-[2-(cyanomethyl)-piperazinyl]-quinolone antibacterials
    • (o) Gubert, S.; Braojos, C.; Anglada, L.; Bolós, J.; Palacin, C. The synthesis and biological activity of new 7-[2-(cyanomethyl)piperazinyl]- and 7-[2-(cyanomethyl)-piperazinyl]-quinolone antibacterials. J. Heterocyclic Chem. 1992, 29, 55-59;
    • (1992) J. Heterocyclic Chem. , vol.29 , pp. 55-59
    • Gubert, S.1    Braojos, C.2    Anglada, L.3    Bolós, J.4    Palacin, C.5
  • 25
    • 0026555048 scopus 로고
    • Potent non-6-fluoro-substituted quinolone antibacterials: Synthesis and biological activity
    • (p) Ledoussal, B.; Bouzard, D.; Coroneos, E. Potent non-6-fluoro- substituted quinolone antibacterials: synthesis and biological activity. J. Med. Chem. 1992, 35, 198-200;
    • (1992) J. Med. Chem. , vol.35 , pp. 198-200
    • Ledoussal, B.1    Bouzard, D.2    Coroneos, E.3
  • 27
    • 0027240178 scopus 로고
    • Quinolone antibacterials: Synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-pyrrolidinyl side chains
    • (r) Laborde, E.; Kiely, J.S.; Culbertson, T.P.; Lesheski, L.E. Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-pyrrolidinyl side chains. J. Med. Chem. 1993, 36, 1964-1970;
    • (1993) J. Med. Chem. , vol.36 , pp. 1964-1970
    • Laborde, E.1    Kiely, J.S.2    Culbertson, T.P.3    Lesheski, L.E.4
  • 28
    • 0027423686 scopus 로고
    • Synthesis of antimicrobial agents. 5. in vivo metabolism of 7-(4-hydroxypiperazin-1-yl)quinolones
    • (s) Uno, T.; Okuno, T.; Kawakami, K.; Sakamoto, F.; Tsukamoto, G. Synthesis of antimicrobial agents. 5. In vivo metabolism of 7-(4- hydroxypiperazin-1-yl)quinolones. J. Med. Chem. 1993, 36, 2711-2715.
    • (1993) J. Med. Chem. , vol.36 , pp. 2711-2715
    • Uno, T.1    Okuno, T.2    Kawakami, K.3    Sakamoto, F.4    Tsukamoto, G.5
  • 29
    • 0033598377 scopus 로고    scopus 로고
    • Glycosylation of fluoroquinolones through direct and oxygenated polymethylene linkages as a sugar-mediated active transport system for antimicrobials
    • Jung, M.E.; Yang, E.C.; Vu, B.T.; Kiankarimi, M.; Spyrou, E.; Kaunitz, J. Glycosylation of fluoroquinolones through direct and oxygenated polymethylene linkages as a sugar-mediated active transport system for antimicrobials. J. Med. Chem. 1999, 42, 3899-3909.
    • (1999) J. Med. Chem. , vol.42 , pp. 3899-3909
    • Jung, M.E.1    Yang, E.C.2    Vu, B.T.3    Kiankarimi, M.4    Spyrou, E.5    Kaunitz, J.6
  • 30
    • 27844522915 scopus 로고
    • Glycosylamines
    • Pigman, W., Horton, D., Eds.; Academic Press: New York
    • (a) Paulsen, H.; Pflughaupt, K.-W. Glycosylamines. In The Carbohydrates; Pigman, W., Horton, D., Eds.; Academic Press: New York, 1972; Vol. IB, 882-892;
    • (1972) The Carbohydrates , vol.1 B , pp. 882-892
    • Paulsen, H.1    Pflughaupt, K.-W.2
  • 31
  • 32
    • 0036592241 scopus 로고    scopus 로고
    • Physicochemical properties of quinolone antibiotics in various environments
    • Park, H.R.; Kim, T.H.; Bark, K.M. Physicochemical properties of quinolone antibiotics in various environments. Eur. J. Med. Chem. 2002, 37, 443-460.
    • (2002) Eur. J. Med. Chem. , vol.37 , pp. 443-460
    • Park, H.R.1    Kim, T.H.2    Bark, K.M.3
  • 33
    • 0001455586 scopus 로고
    • Offenkettige Organo-harnstoffe
    • Georg Thieme Verlag: Stuttgart, New York
    • Petersen, U. Offenkettige Organo-harnstoffe. In Houben-Weyl Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, New York, 1983; Bd. E4, 335-367.
    • (1983) Houben-Weyl Methoden der Organischen Chemie , vol.E4 , pp. 335-367
    • Petersen, U.1
  • 34
    • 0001538228 scopus 로고
    • Acetyl-Zucker-Phosphinimine und Carbodiimide
    • (a) Messmer, A.; Pintér, I.; Szego, F. Acetyl-Zucker-Phosphinimine und Carbodiimide. Angew. Chem. 1964, 76, 227;
    • (1964) Angew. Chem. , vol.76 , pp. 227
    • Messmer, A.1    Pintér, I.2    Szego, F.3
  • 35
    • 0029080631 scopus 로고
    • Synthesis of sugar ureas via phosphinimines
    • (b) Pintér, I.; Kovács, J.; Tóth, G. Synthesis of sugar ureas via phosphinimines. Carbohydr. Res. 1995, 273, 99-108.
    • (1995) Carbohydr. Res. , vol.273 , pp. 99-108
    • Pintér, I.1    Kovács, J.2    Tóth, G.3
  • 36
    • 0000929807 scopus 로고
    • Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine
    • Piskala, A.; Sorm, F. Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine. Coll. Czech. Chem. Commun. 1964, 29, 2060-2076.
    • (1964) Coll. Czech. Chem. Commun. , vol.29 , pp. 2060-2076
    • Piskala, A.1    Sorm, F.2
  • 37
    • 85007931931 scopus 로고
    • Über Azidoderivate der Glucose
    • Bertho, A. Über Azidoderivate der Glucose. Ber. 1930, 63, 836-843.
    • (1930) Ber. , vol.63 , pp. 836-843
    • Bertho, A.1
  • 39
    • 0002933419 scopus 로고
    • Unprotected sugar phosphinimines: A facile route to cyclic carbamates of aminosugars
    • Kovács, J.; Pintér, I.; Messmer, A.; Tóth, G. Unprotected sugar phosphinimines: a facile route to cyclic carbamates of aminosugars. Carbohydr. Res. 1985, 141, 57-65.
    • (1985) Carbohydr. Res. , vol.141 , pp. 57-65
    • Kovács, J.1    Pintér, I.2    Messmer, A.3    Tóth, G.4
  • 40
    • 85162622483 scopus 로고
    • Über die Thiocyansäureester der Glucose und Cellobiose
    • Müller, A.; Wilhelms, A. Über die Thiocyansäureester der Glucose und Cellobiose. Ber. 1941, 74, 698-705.
    • (1941) Ber. , vol.74 , pp. 698-705
    • Müller, A.1    Wilhelms, A.2
  • 41
    • 27844494842 scopus 로고
    • Thiokohlensäure-di-N-Derivate. Thioharnstoffe
    • Georg Thieme Verlag: Stuttgart, New York
    • Kraatz, U. Thiokohlensäure-di-N-Derivate. Thioharnstoffe. In Houben-Weyl Methoden der Organischen Chemie; Georg Thieme Verlag: Stuttgart, New York, 1983; Bd. E4, 484-505.
    • (1983) Houben-Weyl Methoden der Organischen Chemie , vol.E4 , pp. 484-505
    • Kraatz, U.1
  • 42
    • 0024561488 scopus 로고
    • Studies on Prodrugs. 10. Possible mechanism of N-dealkylation of N-masked norfloxacins having several active methylene groups
    • Kondo, H.; Sakamoto, F.; Inoue, Y.; Tsukamoto, G. Studies on Prodrugs. 10. Possible mechanism of N-dealkylation of N-masked norfloxacins having several active methylene groups. J. Med. Chem. 1989, 32, 679-682.
    • (1989) J. Med. Chem. , vol.32 , pp. 679-682
    • Kondo, H.1    Sakamoto, F.2    Inoue, Y.3    Tsukamoto, G.4
  • 45
    • 49049133589 scopus 로고
    • Nuclear magnetic double resonance; the use of difference spectroscopy
    • Sanders, J.K.M.; Mersch, J.D. Nuclear magnetic double resonance; the use of difference spectroscopy. Prog. Nucl. Magn. Reson. Spectrosc. 1982, 15, 353-400.
    • (1982) Prog. Nucl. Magn. Reson. Spectrosc. , vol.15 , pp. 353-400
    • Sanders, J.K.M.1    Mersch, J.D.2
  • 46
    • 0012462196 scopus 로고
    • Proton-polarization transfer enhancement of a heteronuclear spin multiplet with preservation of phase coherency and relative component intensities
    • Pegg, D.T.; Doddrell, D.M.; Bendall, M.R. Proton-polarization transfer enhancement of a heteronuclear spin multiplet with preservation of phase coherency and relative component intensities. J. Chem. Phys. 1982, 77, 2745-2752.
    • (1982) J. Chem. Phys. , vol.77 , pp. 2745-2752
    • Pegg, D.T.1    Doddrell, D.M.2    Bendall, M.R.3
  • 51
    • 0042008023 scopus 로고
    • Apparent ionization constants of water in aqueous organic mixtures and acid dissociation constants of protonated co-solvents in aqueous solution
    • Woolley, E.M. Apparent ionization constants of water in aqueous organic mixtures and acid dissociation constants of protonated co-solvents in aqueous solution. Anal. Chem. 1972, 44 (8), 1520-1523.
    • (1972) Anal. Chem. , vol.44 , Issue.8 , pp. 1520-1523
    • Woolley, E.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.