메뉴 건너뛰기




Volumn 52, Issue 18, 1987, Pages 4007-4013

1,3-Dipolar Cycloaddition Reactions of Pyrazolidinium Ylides with Acetylenes. Synthesis of a New Class of Antibacterial Agents

Author keywords

[No Author keywords available]

Indexed keywords

1H PYRAZOLO[1,2 A]PYRAZOLE DERIVATIVE; 3 ACETYL 7 [2 (2 AMINO 4 THIAZOLYL) 2 METHOXYIMINOACETAMIDO] 8 OXO 1,5 DIAZABICYCLO[3.3.0]OCT 2 ENE 2 CARBOXYLIC ACID; 7 [2 (2 AMINO 4 THIAZOLYL) 2 METHOXYIMINOACETAMIDO] 3 METHOXYCARBONYL 8 OXO 1,5 DIAZABICYCLO[3.3.0]OCT 2 ENE 2 CARBOXYLIC ACID; UNCLASSIFIED DRUG;

EID: 0023629165     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00227a013     Document Type: Article
Times cited : (168)

References (24)
  • 1
    • 84957957591 scopus 로고
    • The Chemistry of Penicillin
    • Clarke, H. T., Johnson, J. R., Robinson, R., Eds.; Princeton Univeristy Press: Princeton, NJ, Wasserman, H. H.; Precopio, F. M.; Liu, T. C. J. Am. Chem. Soc. 1952, 74, 4093. Wasserman, H. H.; Suryanarayana, B.; Koch, R. C.; Tse, R. L. Chem. Ind. (London) 1956, 1022, Todd, D.; Teich, S. J. Am. Chem. Soc. 1953, 75, 1895. Gordon, E. M.; Pluscec, J. Tetrahedron Lett. 1983, 24, 3419. Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Monk, P.; Prout, K. J. Chem. Soc., Chem. Commun. 1983, 250. Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513. Baldwin, J. E.; Adlington, R. M.; Jones, R. H.; Schofield, C. J.; Zarocostas, C.; Greengrass, C. W. J. Chem. Soc., Chem. Commun. 1985, 194.
    • Du Vigneaud, V.; Carpenter, F. H. In The Chemistry of Penicillin; Clarke, H. T., Johnson, J. R., Robinson, R., Eds.; Princeton Univeristy Press: Princeton, NJ, 1949; p 1004. Wasserman, H. H.; Precopio, F. M.; Liu, T. C. J. Am. Chem. Soc. 1952, 74, 4093. Wasserman, H. H.; Suryanarayana, B.; Koch, R. C.; Tse, R. L. Chem. Ind. (London) 1956, 1022, Todd, D.; Teich, S. J. Am. Chem. Soc. 1953, 75, 1895. Gordon, E. M.; Pluscec, J. Tetrahedron Lett. 1983, 24, 3419. Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Monk, P.; Prout, K. J. Chem. Soc., Chem. Commun. 1983, 250. Baldwin, J. E.; Chan, M. F.; Gallacher, G.; Otsuka, M.; Monk, P.; Prout, K. Tetrahedron 1984, 40, 4513. Baldwin, J. E.; Adlington, R. M.; Jones, R. H.; Schofield, C. J.; Zarocostas, C.; Greengrass, C. W. J. Chem. Soc., Chem. Commun. 1985, 194.
    • (1949) , pp. 1004
    • Du Vigneaud, V.1    Carpenter, F.H.2
  • 2
    • 84918118815 scopus 로고
    • During the course of this investigation a U. S. patent appeared disclosing 2-oxo-3-amino-6-(substituted-thio)-l-azabicyclo[3.2.0]hept-6-ene-7-carboxylic acids as antibiotic substances: U. S. Pat. 4 428 960, 1984
    • During the course of this investigation a U. S. patent appeared disclosing 2-oxo-3-amino-6-(substituted-thio)-l-azabicyclo[3.2.0]hept-6-ene-7-carboxylic acids as antibiotic substances: U. S. Pat. 4 428 960, 1984; Chem. Abstr. 1984. 100 (23). 191655.
    • (1984) Chem. Abstr. , vol.100 , Issue.23 , pp. 191655
  • 3
    • 0004030277 scopus 로고
    • Chemistry and Biology of β-Lactam Antibiotics
    • Morin, R. B., Gorman, M., Eds.; Academic Press New York
    • Waxman, D. J.; Strominger, J. L. In Chemistry and Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 3, p 209.
    • (1982) , vol.3 , pp. 209
    • Waxman, D.J.1    Strominger, J.L.2
  • 4
    • 0001000089 scopus 로고
    • The Chemistry & Biology of Lactam Antibiotics
    • Morin, R. B., Gorman, M., Eds.; Academic Press New York
    • Boyd, D. B. In The Chemistry & Biology of β-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic Press: New York, 1982; Vol. 1, pp 437–545.
    • (1982) , vol.1 , pp. 437-545
    • Boyd, D.B.1
  • 8
    • 0000144058 scopus 로고
    • Taylor, E. C.; Davies, H. M. L. J. Org. Chem. 1984, 49, 113. Taylor, E. C.; Davies, H. M. L. Tetrahedron Lett. 1984, 49, 4415. Also see: Moody, C. J.; Pearson, C. J.; Lauton, G. Tetrahedron Lett. 1985, 26, 3167.
    • Taylor, E. C.; Haley, N. F.; Clemens, R. J. J. Am. Chem. Soc. 1981, 103, 7743. Taylor, E. C.; Davies, H. M. L. J. Org. Chem. 1984, 49, 113. Taylor, E. C.; Davies, H. M. L. Tetrahedron Lett. 1984, 49, 4415. Also see: Moody, C. J.; Pearson, C. J.; Lauton, G. Tetrahedron Lett. 1985, 26, 3167.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7743
    • Taylor, E.C.1    Haley, N.F.2    Clemens, R.J.3
  • 9
    • 84981836036 scopus 로고
    • Attempts to prepare the corresponding bis acid by basic hydrolysis of 5 lead to the decomposition of the bicyclic pyrazolidinone ring system.
    • Dorn, H.; Otto, A. Chem. Ber. 1968, 101, 3287. Attempts to prepare the corresponding bis acid by basic hydrolysis of 5 lead to the decomposition of the bicyclic pyrazolidinone ring system.
    • (1968) Chem. Ber. , vol.101 , pp. 3287
    • Dorn, H.1    Otto, A.2
  • 10
    • 0023078342 scopus 로고
    • (b) Jungheim, L. N.; Sigmund, S. K.; Jones, N. D.; Swartzendruber, J. K. Chem. Ber. 1987, 28, 289.
    • Jungheim, L. N.; Sigmund, S. K.; Fisher, J. W. Tetrahedron Lett. 1987, 28, 285. (b) Jungheim, L. N.; Sigmund, S. K.; Jones, N. D.; Swartzendruber, J. K. Chem. Ber. 1987, 28, 289.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 285
    • Jungheim, L.N.1    Sigmund, S.K.2    Fisher, J.W.3
  • 11
    • 0000349036 scopus 로고
    • 1,3-Dipolar Cycloaddition Chemistry
    • Padwa, A., Ed.; John Wiley New York Sons
    • Grashey, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York. 1984; Vol. 1, p 733.
    • (1984) , vol.1 , pp. 733
    • Grashey, R.1
  • 12
    • 84995197765 scopus 로고
    • Dorn, H.; Ozegowski, R.; Radeglia, R. J. Prakt. Chem. 1977, 319, 177. Taylor, E. C.; Clemens, R. J.; Davies, H. M. L. J. Org. Chem. 1983, 48, 4567.
    • Dorn, H.; Zubek, A. Z. Chem. 1968, 7, 270. Dorn, H.; Ozegowski, R.; Radeglia, R. J. Prakt. Chem. 1977, 319, 177. Taylor, E. C.; Clemens, R. J.; Davies, H. M. L. J. Org. Chem. 1983, 48, 4567.
    • (1968) Z. Chem. , vol.7 , pp. 270
    • Dorn, H.1    Zubek, A.2
  • 13
    • 0000182305 scopus 로고
    • For an intramolecular version of this cycloaddition reaction, see: Jacobi, P. A.; Brownstein, A.; Martinelli, M.; Grozinger, K. J. Am. Chem. Soc. 1981, 103, 239.
    • Oppolzer, W. Tetrahedron Lett. 1970, 2199. For an intramolecular version of this cycloaddition reaction, see: Jacobi, P. A.; Brownstein, A.; Martinelli, M.; Grozinger, K. J. Am. Chem. Soc. 1981, 103, 239.
    • (1970) Tetrahedron Lett. , pp. 2199
    • Oppolzer, W.1
  • 14
    • 85022254480 scopus 로고
    • The Acylating Potential of Gamma-Lactam Antibacterials
    • The Base Hydroysis of Bicyclic Pyrazoli-dinones; Abstract #602, XXVI Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC)
    • Indelicato, J. M.; Pasini, C. E. The Acylating Potential of Gamma-Lactam Antibacterials: The Base Hydroysis of Bicyclic Pyrazoli-dinones; Abstract #602, XXVI Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), 1986.
    • (1986)
    • Indelicato, J.M.1    Pasini, C.E.2
  • 16
    • 85022292706 scopus 로고
    • Bicyclic Pyrazolidinones
    • Synthesis and In Vitro Activity of a New Class of Synthetic Antibacterial Agents; Abstract #601, XXVI Interscience Conference on Antimicrobial Agents and Chemitherapy (ICAAC), For example, MICs (μg/mL) of LY173013 vs. Streptococcus pyogenes = 4; Providencia rettgeri = 1; and for LY186826 vs. S. pyogenes = 0.5; P. rettgeri = 0.25.
    • Jungheim, L. N.; Holmes, R. E.; Ott, J. L.; Ternansky, R. J.; Draheim, S. E.; Neel, D. A.; Shepherd, T. A.; Sigmund, S. K. Bicyclic Pyrazolidinones, Synthesis and In Vitro Activity of a New Class of Synthetic Antibacterial Agents; Abstract #601, XXVI Interscience Conference on Antimicrobial Agents and Chemitherapy (ICAAC), 1986. For example, MICs (μg/mL) of LY173013 vs. Streptococcus pyogenes = 4; Providencia rettgeri = 1; and for LY186826 vs. S. pyogenes = 0.5; P. rettgeri = 0.25.
    • (1986)
    • Jungheim, L.N.1    Holmes, R.E.2    Ott, J.L.3    Ternansky, R.J.4    Draheim, S.E.5    Neel, D.A.6    Shepherd, T.A.7    Sigmund, S.K.8
  • 17
    • 85022234594 scopus 로고
    • Inhibition of Peptidoglycan Biosynthesis
    • by LY186826; Abstract #604, XXVI Interscience Conference on Antimicrobial Agents and Chemitherapy (IC-AAC)
    • Hobbs, J. N., Jr.; Andonov-Roland, M. M.; Allen, N. E. Inhibition of Peptidoglycan Biosynthesis by LY186826; Abstract #604, XXVI Interscience Conference on Antimicrobial Agents and Chemitherapy (IC-AAC), 1986.
    • (1986)
    • Hobbs, J.N.1    Andonov-Roland, M.M.2    Allen, N.E.3
  • 18
    • 85022293874 scopus 로고
    • Some Interesting Biological Properties of LY173013 and LY186826
    • Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC) Two Bicyclic Pyrazolidinones; Abstract #603
    • Preston, D. A.; Counter, F. T.; Felty-Duckworth, A. M.; Turner, J. R. Some Interesting Biological Properties of LY173013 and LY186826, Two Bicyclic Pyrazolidinones; Abstract #603, XXVI Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC), 1986.
    • (1986)
    • Preston, D.A.1    Counter, F.T.2    Felty-Duckworth, A.M.3    Turner, J.R.4
  • 21
    • 33751109763 scopus 로고
    • The allyl ester was prepared by substituting allyl alcohol for ethanol.
    • Kishida, Y.; Nakamura, N. Chem. Pharm. Bull. 1969, 17, 2424. The allyl ester was prepared by substituting allyl alcohol for ethanol.
    • (1969) Chem. Pharm. Bull. , vol.17 , pp. 2424
    • Kishida, Y.1    Nakamura, N.2
  • 24
    • 85022307730 scopus 로고
    • describes the synthesis of the sec-butyl ester of perfluorobutynoate. Chemical Abstracts
    • Chemical Abstracts (Chem. Abstr. 1983, 99, 38008r) describes the synthesis of the sec-butyl ester of perfluorobutynoate.
    • (1983) Chem. Abstr. , vol.99 , pp. 38008r


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.