메뉴 건너뛰기




Volumn 63, Issue 22, 1998, Pages 7600-7618

S-aminosulfeniminopenicillins: Multimode β-lactamase inhibitors and template structures for penicillin-based β-lactamase substrates as prodrugs

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; N CARBETHOXY S AMINOSULFENIMINOPENICILLANATE 1 SULFONE; N METHYL N TOSYL S AMINOSULFENIMINOPENICILLANIC ACID; PENICILLIN DERIVATIVE; PENICILLIN G; PIPERACILLIN; PRODRUG; S AMINOSULFENIMINOPENICILLIN DERIVATIVE; SULFONAMIDE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032582734     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970737f     Document Type: Article
Times cited : (17)

References (89)
  • 10
    • 0017131006 scopus 로고
    • The inherent reactivity of cephalosporins, resulting in elimination of the 3′ substitutent after cleavage of the β-lactam ring, has been harnessed in the development of dual-action structures producing effectively, cephalosporin based, β-lactamase substrate prodrugs: (a) O'Callaghan, C. H.; Sykes, R. B.; Staniforth, S. E. Antimicrob. Agents Chemother. 1976, 245.
    • (1976) Antimicrob. Agents Chemother. , pp. 245
    • O'Callaghan, C.H.1    Sykes, R.B.2    Staniforth, S.E.3
  • 18
    • 33847489194 scopus 로고    scopus 로고
    • (8) Included in Supporting Information.
    • , vol.8
  • 24
    • 0027223591 scopus 로고
    • Ampac 5.0, 1994, Semichem, 7204 Mullen, Shawnee, KS 66216.
    • Ampac 5.0, 1994, Semichem, 7204 Mullen, Shawnee, KS 66216. For details of SAM1 see: Dewar, J. S.; Jie, C.; Yu, J. Tetrahedron 1993, 49, 5003.
    • (1993) Tetrahedron , vol.49 , pp. 5003
    • Dewar, J.S.1    Jie, C.2    Yu, J.3
  • 36
    • 0022367375 scopus 로고
    • For examples of a similar pattern of chemical shift changes on opening the β-lactam ring of a penicillin followed by closure to yield bicyclic structures with the thiazolidine ring fused to five-membered rings, see: (a) Marchand-Brynaert, J.; Ghosez, L. Bull. Soc. Chim. Belg. 1985, 94, 1021.
    • (1985) Bull. Soc. Chim. Belg. , vol.94 , pp. 1021
    • Marchand-Brynaert, J.1    Ghosez, L.2
  • 42
    • 33847455093 scopus 로고
    • Sammes, P. G., Ed.; Ellis Horwood: Chichester, Chapter 2
    • (b) A number of other penicillin, and closely related, structures showing this pattern of chemical shifts for H5/H3 are given in Topics in Antibiotic Chemistry, Vol. 4; Sammes, P. G., Ed.; Ellis Horwood: Chichester, 1980; Chapter 2.
    • (1980) Topics in Antibiotic Chemistry , vol.4
  • 43
    • 33847478765 scopus 로고    scopus 로고
    • 3, but were able to so using the stronger base DBN.
    • 3, but were able to so using the stronger base DBN.
  • 45
    • 0003940737 scopus 로고
    • Academic Press: New York, Chapter 4 and references therein
    • Block, E. Reactions of Organosulfur Compounds; Academic Press: New York, 1978 Chapter 4 and references therein.
    • (1978) Reactions of Organosulfur Compounds
    • Block, E.1
  • 48
    • 14444283586 scopus 로고    scopus 로고
    • note
    • - for a very short reaction time, see Experimental Section for details.
  • 50
    • 0346480614 scopus 로고
    • and references therein
    • (c) The ability of sulfur to stabilize an adjacent anion is well documented: Wiberg, K. B.; Castejon, H. J. Am. Chem. Soc. 1994, 116, 10489 and references therein.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10489
    • Wiberg, K.B.1    Castejon, H.2
  • 55
    • 14444282574 scopus 로고    scopus 로고
    • note
    • 5cm was isolated as the free acid. For enzymatic studies 50 μL of a THF solution of 5cm-free acid was added to the aqueous buffer containing the β-lactamase enzyme (see Experimental Section).
  • 57
    • 14444276986 scopus 로고    scopus 로고
    • note
    • Enzyme inactivation was found to be time dependent. An incubation time of 10 min proved to be convenient. The partition number, when evaluated in this way, can vary with the incubation time used: see ref 3e.
  • 58
    • 33847431100 scopus 로고
    • Fersht, A., Ed. W. H. Freeman and Company: New York, Chapter 3
    • (a) Fersht, A., Ed. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman and Company: New York, 1985; Chapter 3.
    • (1985) Enzyme Structure and Mechanism, 2nd Ed.
  • 59
    • 14444277240 scopus 로고    scopus 로고
    • note
    • 3 which has been shown to be the case for a variety of β-lactamases (see ref 33).
  • 61
    • 14444271568 scopus 로고    scopus 로고
    • note
    • a of the N-conjugate acid of a closely related structure is 5.14: see ref 19.
  • 69
    • 33847426428 scopus 로고    scopus 로고
    • In all cases no recovery of enzyme activity was detected after up to 19 h.
    • In all cases no recovery of enzyme activity was detected after up to 19 h.
  • 72
    • 33847455827 scopus 로고    scopus 로고
    • (43) (a) These tests were carried out by CPA Laboratories, Birkenhead, Wirral, U.K.
    • , vol.43
  • 73
    • 33847479084 scopus 로고    scopus 로고
    • (44) These tests were carried out at the Centre for Research in AntiInfectives and Biotechnology, Creighton University, Omaha, NB.
    • , vol.44
  • 82
    • 0001379690 scopus 로고
    • This is a modification of the procedure reported in Katz, T. J.; Shi, S. J. Org. Chem. 1994, 59, 8297.
    • (1994) J. Org. Chem. , vol.59 , pp. 8297
    • Katz, T.J.1    Shi, S.2
  • 83
    • 33847457556 scopus 로고    scopus 로고
    • This is a modification of the procedure reported in ref 50
    • This is a modification of the procedure reported in ref 50.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.