Skip to main content
SpringerLink
Log in

Non β-Lactam Analogs of Penicillins and Cephalosporins

  • Chapter
Recent Progress in the Chemical Synthesis of Antibiotics

Abstract

The remarkable biological effect of β-Iactam antibiotics results from their capacity to disrupt the biosynthesis of the bacterial cell wall. They do this by inhibiting D,D-transpeptidases, membranebound serine peptidases which are involved in the peptidoglycan cross-linking. The extensive use of penicillins and other β-Iactam antibiotics in medicine over the last forty years has given rise to an increasing number of resistant bacteria, a phenomenon mainly due to the production of β-Iactamases. Therefore, a current challenge in antibiotherapy is the production of new structures which will overcome the defense mechanisms of the bacteria. Non β-Iactams may provide a solution to this problem. In the last few years, several research groups have launched programmes to synthesise rationally-designed compounds which are not β-Iactams, but which hopefully inhibit the same enzymes. This review describes their efforts, successes and failures.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

PBP:

penicillin binding protein

PNB:

para-nitro benzyl

PMB:

para-methoxylbenzyl

TCE:

trichloroethyl

PIV:

pivaloyloxymethyl

EWG:

electron-withdrawing group

FtN:

phthalimido

Tos:

tosyl

ATMO:

2-(amino-4-thiazolyl)-2-(methoxy)-iminoacetyl

References

  1. Waxman DJ, Strominger JL (1982) In: Morin RB, Gorman M (eds) Chemistry and biology of β-lactam antibiotics, Academic, New York, vol 3, p 209

    Google Scholar 

  2. Durckheimer W, Blumbach J, Latrell R, Scheunemann KH (1985) Angew Chem Internat Edit 24: 180

    Article  Google Scholar 

  3. Frère JM, Joris B (1985) CRC Critical Rev Microb 11: 299

    Article  Google Scholar 

  4. Lamotte-Brasseur J, Dive G, Ghuysen JM (1984) Eur J Med Chem-Chim Ther 19: 319

    CAS  Google Scholar 

  5. Ernest I (1982) In: Morin RB, Gorman M (eds) Chemistry and biology of β-lactam antibiotics, Academic, New York, vol 2, p 315

    Google Scholar 

  6. Nagata W, Narisada M, Yoshida T (1982) In: Morin RB, Gorman M (eds) Chemistry and biology of β-lactam antibiotics, Academic, New York, vol 2, p 1

    Google Scholar 

  7. Woulfe SR, Miller MJ (1985) J Med Chem 28: 1447

    Article  CAS  Google Scholar 

  8. Cartwright SJ, Waley SG (1983) Med Res Rev 3(4): 341

    Article  CAS  Google Scholar 

  9. Herzberg O, Moult J (1987) Science 236: 694

    Article  CAS  Google Scholar 

  10. Joris B, Ghuysen JM, Dive G, Renard A, Dideberg O, Charlier P, Frère JM, Kelly JA, Boyington JC, Moews PC, Knox JR (1988) Biochem J 250: 313

    CAS  Google Scholar 

  11. Woodward RB (1977) In: Elks J (ed) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 28, p 167

    Google Scholar 

  12. De Poortere M, Marchand-Brynaert J, Ghosez L (1974) Angew Chem Internat Edit 13: 267

    Article  Google Scholar 

  13. Ghosez L, Marchand-Brynaert J (1976) Adv Org Chem 9 (Part II): 421

    Google Scholar 

  14. Marchand-Brynaert J, Moya-Portuguez M, Lesuisse D, Ghosez L (1980) J Chem Soc Chem Commun 173

    Google Scholar 

  15. Marchand-Brynaert J, Moya-Portuguez M, Huber I, Ghosez L (1983) J Chem Soc Chem Commun 818

    Google Scholar 

  16. Ghosez L, Bogdan S, Cérésiat M, Frydrych C, Marchand-Brynaert J, Moya-Portuguez M, Hubert I (1987) Pure Appl Chem 59: 393

    Article  CAS  Google Scholar 

  17. Haveaux B, Dekoker A, Rens M, Sidani AR, Toye J, Ghosez L (1980) Org Synth 59: 26

    CAS  Google Scholar 

  18. Courmont V, Marchand-Brynaert J, Ghosez L (1979) (unpublished results)

    Google Scholar 

  19. Bachi MD, Braiman R (1980) J Chem Soc Perkin Trans I, 11

    Article  Google Scholar 

  20. Van Camp A, Marchand-Brynaert J, Ghosez L (1976) (unpublished results)

    Google Scholar 

  21. Graf R, Guenther D, Jensen H, Matterstock K (1963) Ger Offen 1,144,718; Chem Abstr 59: 6368

    Google Scholar 

  22. Campbell MM, Harcus RG, Nelson KH (1978) J Chem Soc Perkin Trans I, 817

    Article  Google Scholar 

  23. Marchand-Brynaert J, Ghosez L (1982) (unpublished results)

    Google Scholar 

  24. Van Camp A, Goossens D, Moya-Portuguez M, Marchand-Brynaert J, Ghosez L (1980) Tetrahedron Lett 21: 3081

    Article  Google Scholar 

  25. Goossens D, Marchand-Brynaert J, Ghosez L (1983) (unpublished results)

    Google Scholar 

  26. Ratcliffe RW, Christensen BG (1973) Tetrahedron Lett 4645

    Google Scholar 

  27. Wojkowski PW, Dolfini JE, Kocy O, Cimarusti CM (1975) J Am Chem Soc 97: 5628

    Article  Google Scholar 

  28. Murphy BP, Pratt RF (1988) Biochem. J. 256: 669

    CAS  Google Scholar 

  29. Murphy BP, Pratt RF (1989) Biochem J 258: 765

    CAS  Google Scholar 

  30. Gilpin ML, Harbridge JB, Howarth TT (1981) J Chem Soc Chem Commun 929 and (1987) J Chem Soc Perkin Trans I, 1369

    Google Scholar 

  31. Taylor EC, Clemens RJ, Davies HML, Haley NF (1981) J Am Chem Soc 103: 7659 and 7661

    Article  CAS  Google Scholar 

  32. Taylor EC, Haley NF, Clemens RJ (1981) J Am Chem Soc 103: 7743

    Article  CAS  Google Scholar 

  33. Taylor EC, Clemens RJ, Davies HML (1983) J Org Chem 48: 4567

    Article  CAS  Google Scholar 

  34. Taylor EC, Davies HML (1984) J Org Chem 49: 113

    Article  CAS  Google Scholar 

  35. Taylor EC, Davies HML, Hinkle JS (1986) J Org Chem 51: 1530

    Article  CAS  Google Scholar 

  36. Taylor EC, Davies HML (1986) J Org Chem 51: 1537

    Article  CAS  Google Scholar 

  37. Taylor EC, Hinkle JS (1987) J Org Chem 52: 4107

    Article  CAS  Google Scholar 

  38. Lawton G, Moody CJ, Pearson CJ (1984) J Chem Soc Chem Commun 754

    Google Scholar 

  39. Moody CJ, Pearson CJ (1985) Tetrahedron Lett 26: 3167

    Article  CAS  Google Scholar 

  40. Lawton G, Moody CJ, Pearson CJ (1987) J Chem Soc Perkin Trans I, 877

    Article  Google Scholar 

  41. Lawton G, Moody CJ, Pearson CJ, Williams DJ (1987) J Chem Soc Perkin Trans I, 885

    Article  Google Scholar 

  42. Moody CJ, Pearson CJ, Lawton G (1985) Tetrahedron Lett 26: 3171

    Article  CAS  Google Scholar 

  43. Lawton G, Moody CJ, Pearson CJ (1987) J Chem Soc Perkin Trans I, 899

    Article  Google Scholar 

  44. Cimarusti CM, Sykes RB (1984) Med Res Rev 4: 1

    Article  CAS  Google Scholar 

  45. Skotnicki JS (1986) J Antibiot 39: 471

    CAS  Google Scholar 

  46. Wells JC, Hunter JC, Astle GL, Sherwood JC, Ricca CM, Trejo WH, Bonner DP, Sykes RB (1982) J Antibiot 35: 814

    CAS  Google Scholar 

  47. Parker WL, Rathnum ML, Liu W-C (1982), J Antibiot 35: 900

    CAS  Google Scholar 

  48. Wells JC, Trejo WH, Principe PA, Sykes RB (1984) J Antibiot 37: 802

    CAS  Google Scholar 

  49. Tymiak AA, Culver CA, Malley MF, Gougoutas JZ (1985) J Org Chem 50: 5491

    Article  CAS  Google Scholar 

  50. Hebert RB, Knaggs AR (1988) Tetrahedron Lett 29: 6353

    Article  Google Scholar 

  51. Cavagna F, Koller W, Linkies A, Rehling H, Reuschling D (1982) Angew Chem Suppl 1201

    Google Scholar 

  52. Koller W, Linkies A, Rehling H, Reuschling D (1983) Tetrahedron Lett 24: 2131

    Article  CAS  Google Scholar 

  53. Agathocleus D, Buckwell S, Proctor P, Page MI (1985) In: Brown AG, Roberts SM (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 52, chap 2

    Google Scholar 

  54. Gordon EM, Pluscec J, Ondetti MA (1981) Tetrahedron Lett 22: 1871

    Article  CAS  Google Scholar 

  55. Lange G, Savard ME, Viswanatha T, Dmitrienko GI (1985) Tetrahedron Lett 26: 1791

    Article  CAS  Google Scholar 

  56. Tamczuk BE (1980) Dissertation Abstracts 41: 576

    Google Scholar 

  57. Bartolone JB, Hite GJ, Kelly JA, Knox JR (1985) In: Brown AG, Roberts SM (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 52, chap 22

    Google Scholar 

  58. Lowe G, Swain S (1983) J Chem Soc Chem Commun 1279

    Google Scholar 

  59. Lowe G, Swain S (1985) J Chem Soc Perkin Trans I, 391

    Article  Google Scholar 

  60. Lowe G, Swain S (1985) In: Brown AG, Roberts SM (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 52, chap 14

    Google Scholar 

  61. Cocuzza AJ, Boswell AG (1985) Tetrahedron Lett 26: 5363

    Article  CAS  Google Scholar 

  62. Bellus D, Ernst B (1988) Angew Chem Internat Edit 27: 821

    Article  Google Scholar 

  63. Ernst B (1986) (unpublished results) from FNRS meeting, Belgium

    Google Scholar 

  64. Meth-Cohn O, Reason AJ, Roberts SM (1982) J Chem Soc Chem Commun 90

    Google Scholar 

  65. Bartlett PA, Marlowe CK (1983) Biochemistry 22: 4618 and references cited therein

    Article  CAS  Google Scholar 

  66. Sammes PG, Smith S, Woolley GT (1984) J Chem Soc Perkin Trans I, 2603

    Article  Google Scholar 

  67. Petursson S, Waley SG (1983) Tetrahedron 39: 2465

    Article  CAS  Google Scholar 

  68. Sammes PG, Smith S (1982) J Chem Soc, Chem Commun 1143

    Google Scholar 

  69. Sammes PG, Smith S (1983) J Chem Soc Chem Commun 682

    Google Scholar 

  70. Sammes PG, Smith S (1984) J Chem Soc Perkin Trans I, 2415

    Article  Google Scholar 

  71. Agathocleous D, Cox G, Page MI (1986) Tetrahedron Lett 27: 1631

    Article  CAS  Google Scholar 

  72. Johnson PY, Hatch III CE (1975) J Org Chem 40: 3502 and 3510

    Article  CAS  Google Scholar 

  73. Hatch CE, Johnson PY (1974) Tetrahedron Lett 2719

    Google Scholar 

  74. Williams RM, Lee BH, Miller S, Anderson OP (1989) In: Bentley PH, Southgate R (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 70, chap 7: and J Am Chem Soc 111: 1073

    Google Scholar 

  75. Page MI (1987) Adv Phys Org Chem 23: 165

    Article  CAS  Google Scholar 

  76. Du Vigneaud V, Carpenter FH (1949) In: Clarke HT, Johnson JR, Robinson R (eds) The chemistry of penicillin, Princeton University Press, p 1004

    Google Scholar 

  77. Wasserman HH, Suryanarayana Y, Koch RC, Tse RL (1956) Chem and Ind 1022

    Google Scholar 

  78. Baldwin JE, Norriss WJ, Freeman RT, Bradley M, Adlington RM, Long-Fox S, Schofield CJ (1988) J Chem Soc Chem Commun 1128

    Google Scholar 

  79. Maki Y, Sako M, Kurahashi N, Hirota K (1988) J Chem Soc Chem Commun 110

    Google Scholar 

  80. Bose AK, Manhas MS, Chawla HPS, Dayal B (1975) J Chem Soc Perkin Trans I, 1880

    Article  Google Scholar 

  81. Bird CW (1966) Tetrahedron 22: 2489

    Article  CAS  Google Scholar 

  82. Peck RL, Folkers K (1949) In: Clarke HT, Johnson JR, Robinson R (eds) The chemistry of penicillin, Princeton University Press, p 144

    Google Scholar 

  83. Baldwin JE, Chan MF, Gallacher G, Monk P, Prout K (1983) J Chem Soc Chem Commun 250

    Google Scholar 

  84. Baldwin JE, Chan MF, Gallacher G, Otsuka M, Monk P, Prout K (1984) Tetrahedron 40:4513

    Article  CAS  Google Scholar 

  85. Baldwin JE, Adlington RM, Jones RH, Schofield CJ, Zaracostas C, Greengrass CW (1986) Tetrahedron 42: 4879

    Article  CAS  Google Scholar 

  86. Baldwin JE, Adlington RM, Jones RH, Schofield CJ, Zarocostas C, Greengrass CW (1985) J Chem Soc Chem Commun 194

    Google Scholar 

  87. Cohen NC (1983) J Med Chem 26: 259

    Article  CAS  Google Scholar 

  88. Boyd DB, Elzey TK, Hatfield LD, Kinnick MD, Morin Jr JM (1986) Tetrahedron Lett 27:3453

    Article  CAS  Google Scholar 

  89. Allen NE, Boyd DB, Campbell JB, Deeter JB, Elzey TK, Foster BJ, Hatfield LD, Hobbs Jr JN, Homback WJ, Hunden DC, Jones ND, Kinnick MD, Morin Jr JM, Munroe JE, Swartzendruber JK, Vogt DG (1989) Tetrahedron 45: 1905

    Article  CAS  Google Scholar 

  90. Lang M, Prasad K, Holick W, Gosteli J, Ernest I, Woodward RB (1979) J Am Chem Soc 101: 6296

    Article  CAS  Google Scholar 

  91. Baldwin JE, Lowe C, Schofield CJ (1986) Tetrahedron Lett 27: 3461

    Article  CAS  Google Scholar 

  92. Heck JV (1984) US Patent US 4,428,960; Chem Abstr 100: 191655h

    Google Scholar 

  93. Boyd DB, Foster BJ, Hatfield LD, Hornback WJ, Jones ND, Munroe JE, Swartzendruber JK (1986) Tetrahedron Lett 27: 3457

    Article  CAS  Google Scholar 

  94. Salzmann TN, Ratcliffe RW, Christensen BG, Bouffard FA (1980) J Am Chem Soc 102: 6161

    Article  CAS  Google Scholar 

  95. Hashiguchi S, Natsugari H, Ochiai M (1988) J Chem Soc Perkin Trans I, 2345

    Article  Google Scholar 

  96. Freidinger RM, Perlow DS, Veber DF (1982) J Org Chem 47: 104

    Article  CAS  Google Scholar 

  97. De Lombaert S, Marchand-Brynaert J, Ghosez L (1986) (unpublished results)

    Google Scholar 

  98. Floyd DM (1982) J Org Chem 47: 5160

    Article  CAS  Google Scholar 

  99. Miller MJ (1986) Acc Chem Res 19: 49

    Article  CAS  Google Scholar 

  100. Crossley MJ, Crumbie RL, Fung YM, Potter JJ, Pleger MA (1987) Tetrahedron Lett 28: 2883

    Article  CAS  Google Scholar 

  101. Wasserman HH, Precopio FM, Liu T-Ch (1952) J Am Chem Soc 74: 4093

    Article  CAS  Google Scholar 

  102. Sheehan JC, Nakajima K, Chacko E (1979) Heterocycles 13: 227

    Article  CAS  Google Scholar 

  103. Bycroft BW, King TJ, Shute RE (1983) Tetrahedron Lett 24: 601

    Article  CAS  Google Scholar 

  104. Jephcote VJ, John DI, Williams DJ (1986) J Chem Soc Perkin Trans I, 2195

    Article  Google Scholar 

  105. John DI (1985) In: Bentley PH, Southgate R (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 70, chap 13

    Google Scholar 

  106. Gordon EM, Pluscec J (1983) Tetrahedron Lett 24: 3419

    Article  CAS  Google Scholar 

  107. Gordon EM, Chang HW, Cimarusti CM, Toeplitz B, Gougoutas JZ (1980) J Am Chem Soc 102: 1690

    Article  CAS  Google Scholar 

  108. Jungheim LN, Sigmund SK, Fisher JW (1987) Tetrahedron Lett 28: 285

    Article  CAS  Google Scholar 

  109. Indelicato JM, Pasini CE (1988) J Med Chem 31: 1227

    Article  CAS  Google Scholar 

  110. Dorn H, Otto A (1968) Chem Ber 101: 3287

    Article  CAS  Google Scholar 

  111. Jungheim LN, Sigmund SK, Jones ND, Swartzendruber (1987) Tetrahedron Lett 28: 289

    Article  CAS  Google Scholar 

  112. Jungheim LN, Sigmund SK (1987) J Org Chem 52: 4007

    Article  CAS  Google Scholar 

  113. Jungheim LN, Barnett CJ, Gray JE, Horcher LH, Shepherd TA, Sigmund SK (1988) Tetrahedron 44: 3119

    Article  CAS  Google Scholar 

  114. Jungheim LN, Sigmund SK, Holmes RE, Barnett CJ, Ternansky RJ (1986) Eur Patent Appl EP 202,046

    Google Scholar 

  115. Ternansky RJ, Draheim SE (1989) In: Bentley PH, Southgate R (eds) Recent advances in the chemistry of β-lactams antibiotics, Chem Soc Special Public, 70, chap 9

    Google Scholar 

  116. Ternansky RJ, Draheim SE (1988) Tetrahedron Lett 29: 6569

    Article  CAS  Google Scholar 

  117. Gale EF, Cuncliffe E, Reynolds PE, Richmond MH, Waring MJ (1981) The molecular basis of antibiotic action, John Wiley, p 65

    Google Scholar 

  118. Tsuji A, Yamana T, Matsutani S, Tsuji N (1977) Heterocycles 8: 153

    Article  CAS  Google Scholar 

  119. Harada S, Tsubotani S, Hida T, Ono H, Okazaki H (1986) Tetrahedron Lett 27: 6229

    Article  CAS  Google Scholar 

  120. Nozaki Y, Katayama N, Ono H, Tsubotani S, Harada S, Okazaki H, Nakao Y (1987) Nature 325: 179

    Article  CAS  Google Scholar 

  121. Nakao Y (1989) In: Bentley PH, Southgate R (eds) Recent advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 70, chap 8

    Google Scholar 

  122. Natsugari H, Kawano Y, Morimoto A, Yoshioka K, Ochiai M (1987) J Chem Soc Chem Commun 62

    Google Scholar 

  123. Harada S, Tsubotani S, Hida T, Koyama K, Kondo M, Ono H (1988) Tetrahedron 44: 6589

    Article  CAS  Google Scholar 

  124. Baldwin JE, Ng Si C, Pratt AJ (1987) Tetrahedron Lett 28: 4319

    Article  CAS  Google Scholar 

  125. Marchand-Brynaert J, Bounkhala-Khrouz Z, Carretero JC, Davies J, Ferroud D, van Keulen BJ, Serckx-Poncin B, Ghosez L (1989) In: Bentley PH, Southgate R (eds) Recent Advances in the chemistry of β-lactam antibiotics, Chem Soc Special Public 70, chap 10

    Google Scholar 

  126. Bremmer DH, Campbell MM, Johnson G (1976) J Chem Soc Chem Commun 293

    Google Scholar 

  127. Bremmer DH, Campbell MM, Johnson G (1976) J Chem Soc Perkin Trans I, 1918

    Article  Google Scholar 

  128. Jaxa-Chamiec AA, Mc Donald WS, Sammer PG, Talekar RR (1982) Tetrahedron Lett 23: 2813

    Article  CAS  Google Scholar 

  129. Marchand-Brynaert J, Ghosez L (1985) Bull Soc Chim Belg 94: 1021

    Article  CAS  Google Scholar 

  130. Declercq JP, Van Meerssche M, Marchand-Brynaert J (1986) Bull Soc Chim Belg 95: 241

    Article  CAS  Google Scholar 

  131. Marchand-Brynaert J (1987) Compte-rendu des Journées Franco-Belges de Pharmacochimie, Editions INSERM, Lille (France)

    Google Scholar 

  132. Marchand-Brynaert J, Ghosez L (1986) (unpublished results)

    Google Scholar 

  133. Vlietinck A, Roets E, Claes P, Janssen G, Vanderhaeghe H (1973) J Chem Soc Perkin Trans I, 937

    Article  Google Scholar 

  134. Chauvette RR, Pennington PA, Ryan CW, Cooper RDG, José FL, Wright IG, Van Heyningen EM, Huffman GW (1971) J Org Chem 36: 1259

    Article  CAS  Google Scholar 

  135. Ferres H (1980) Chem and Ind 11: 435

    Google Scholar 

  136. Frère JM (1986) (unpublished results)

    Google Scholar 

  137. Batchelor FR, Gazzard D, Nayler JHC (1961) Nature 191: 910

    Article  CAS  Google Scholar 

  138. Johnson DA, Hardcastle Jr GA (1961) J Am Chem Soc 83: 3534

    Article  CAS  Google Scholar 

  139. Ernest I, Gostelli J, Woodward RB (1979) J Am Chem Soc 101: 6301 and references cited therein

    Article  CAS  Google Scholar 

  140. Marchand-Brynaert J, Vanlierde H, Ghosez L (1988) Bull Soc Chim Belg 97: 1081

    Article  CAS  Google Scholar 

  141. Slee AM, Wusnola MA, Mc Ripley RJ, Zajac I, Zawada MJ, Bartholomew PT, Gregory WA, Forbes M (1987) Antimicrob Agents Chemother 31: 1791

    CAS  Google Scholar 

  142. Barry AL (1988) Antimicrob Agents Chemother 32: 150

    CAS  Google Scholar 

  143. Neu HC (1988) Antimicrob Agents Chemother 32: 580

    CAS  Google Scholar 

  144. Daly JS (1988) J Antimicrob Chemother 21: 721

    Article  CAS  Google Scholar 

  145. Hauser D, Sigg HP (1967) Helv Chim Acta 50: 1327

    Article  CAS  Google Scholar 

  146. De Meester F, Frère JM, Piette JL, Vanderhaeghe H (1985) J Labelled Compounds and Radiopharm 22: 415

    Article  Google Scholar 

  147. Todd D, Teich S (1953) J Am Chem Soc 75: 1895

    Article  CAS  Google Scholar 

  148. Steele J, Stoodley RJ (1982) J Chem Soc Chem Commun 1215

    Google Scholar 

  149. John DI, Tyrrell ND, Thomas EJ, Bentley PH, Williams DJ (1982) J Chem Soc Chem Commun 76

    Google Scholar 

  150. Jephcote VJ, John DI (1984) Tetrahedron Lett 25: 2915

    Article  CAS  Google Scholar 

  151. Jephcote VJ, Jowett IC, John DI, Edwards PD, Luk K, Slawin AM, Williams DJ (1986) J Chem Soc Perkin Trans I, 2187

    Article  Google Scholar 

  152. Jephcote VJ, John DI (1984) Tetrahedron Lett 25: 2919

    Article  CAS  Google Scholar 

  153. Burgi HB, Dunitz JD, Lehn JM, Wipff G (1974) Tetrahedron 30: 1563

    Article  Google Scholar 

  154. Haddadin MJ, Freeman JP (1985) In: Hassner A (ed) The chemistry of heterocyclic compounds, small ring heterocycles, John Wiley, vol 42, part 3, chap 3

    Google Scholar 

  155. Allinger NL, Tai JC, Wu FT (1970) J Am Chem Soc 92: 579

    Article  CAS  Google Scholar 

  156. Marchand-Brynaert J, Bounhkala-Khrouz Z, van Keulen BJ, Vanlierde H, Ghosez L (1989) Israël J Chem 29: 247

    CAS  Google Scholar 

  157. Marchand-Brynaert J, Bounkhala-Khrouz Z, Vanlierde H, Ghosez L (1990) Heterocycles 34: 0000.

    Google Scholar 

  158. Hann MM, Sammes PG, Kennewell PD, Taylor JB (1982) J Chem Soc Perkin Trans I, 307

    Article  Google Scholar 

  159. Carretero JC, Demillequand M, Ghosez L (1987) Tetrahedron 43: 5125

    Article  CAS  Google Scholar 

  160. Carretero JC, Ghosez L (1987) Tetrahedron Lett 28: 1101

    Article  CAS  Google Scholar 

  161. Bartlett PA, Vanmaele LJ, Kezer WB (1986) Bull Soc Chim Fr 776

    Google Scholar 

  162. Huber JW, Gilmore WF, Robertson LW (1975) J Med Chem 18: 106

    Article  CAS  Google Scholar 

  163. Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS (1978) Nature 272: 56

    Article  CAS  Google Scholar 

  164. Allen JG, Atherton FR, Hall MJ, Hassall CH, Holmes SW, Lambert RW, Nisbet LJ, Ringrose PS (1979) Antimicrob Agents Chemother 15: 684

    CAS  Google Scholar 

  165. Kametani T, Kigasawa K, Hiiragi M, Wakisaka K, Haga S, Sugi H, Tanigawa K, Suzuki Y, Fukawa K, Irino O, Saita O, Yamabe S (1981) Heterocycles 16: 1205

    Article  CAS  Google Scholar 

  166. Campbell MM, Carruthers N (1980) J Chem Soc Chem Commun 730

    Google Scholar 

  167. Campbell MM, Carruthers N, Mickel SJ (1982) Tetrahedron 38: 2513

    Article  CAS  Google Scholar 

  168. Bessley T, Gascoyne N, Knott-Hunziker V, Petursson S, Waley SG, Jaurin B, Grundström T (1983) Biochem J 209: 229

    Google Scholar 

  169. Crompton IE, Cuthbert BK, Lowe G, Waley SG (1988) Biochem J 251: 453

    CAS  Google Scholar 

  170. Neher R, Wettstein A, Miescher K (1946) Helv Chim Acta 29: 1815

    Article  CAS  Google Scholar 

  171. Neher R, Spillmann M, Werner LH, Wettstein A, Miescher K (1946) Helv Chim Acta 29: 1875

    Article  Google Scholar 

  172. Holly FW, Peel EW, Luz EL, Folkers K (1952) J Am Chem Soc 74: 4539

    Article  Google Scholar 

  173. Sahasrabudhe S, Marchand-Brynaert J, Ghosez L (1986) (unpublished results)

    Google Scholar 

  174. Henery-Logan KR, Limburg AM (1966) Tetrahedron Lett 4615

    Google Scholar 

  175. Mardle MJ, Nayler JHC, Rustidge DW, Waddingtoh HRJ (1968) J Chem Soc (C) 237

    Google Scholar 

  176. Miller DB, Nayler JHC, Waddington HRJ (1968) J Chem Soc (C) 242

    Google Scholar 

  177. Nieto M, Perkins HR, Leyh-Bouille M, Frère JM, Ghuysen JM (1973) Biochem J 131: 163

    CAS  Google Scholar 

  178. Smissman EE, Terada A, El-Antably S (1976) J Med Chem 19: 165

    Article  CAS  Google Scholar 

  179. Chu DT, Martin JR, Thomas AM (1982) US Patent 4,309,342

    Google Scholar 

  180. Hagen EA, Bergan T, Aasen AJ (1984) Acta Chem Scand B38: 5

    Article  CAS  Google Scholar 

  181. Loennechen T, Bergan T, Sydness LK, Aasen AJ (1984) Acta Chem Scand B38: 647

    Article  CAS  Google Scholar 

  182. Rasmussen JR, Strominger JL (1978) Proc Natl Acad Sci USA 75: 84

    Article  CAS  Google Scholar 

  183. Pratt RF, Govardhan CP (1984) Proc Natl Acad Sei USA 81: 1302

    Article  CAS  Google Scholar 

  184. Pratt RF, Faraci WS, Govardhan CP (1985) Anal Biochem 144: 204

    Article  CAS  Google Scholar 

  185. Govardhan CP, Pratt RF (1987) Biochemistry 26: 3385

    Article  CAS  Google Scholar 

  186. Bogdan S, Marchand-Brynaert J, Ghosez L (1985) (unpublished results)

    Google Scholar 

  187. Couder J, Vander Elst P, Tourwé D, Van Binst G (1987) Bull Soc Chim Belg 96: 629

    Article  CAS  Google Scholar 

  188. Tanizawa K, Santoh K, Kanaoka Y (1989) Chem Pharm Bull 37: 824

    CAS  Google Scholar 

  189. Baldwin JE, Blackburn JM, Sako M, Schofield CJ (1989) J Chem Soc Chem Commun 970

    Google Scholar 

  190. Baldwin JE, Freeman RT, Schofield C (1989) Tetrahedron Lett 30: 4019

    Article  CAS  Google Scholar 

  191. Baldwin JE, Freeman RT, Lowe C, Schofield CJ, Lee E (1989) Tetrahedron 45: 4537

    Article  CAS  Google Scholar 

  192. Jungheim LN (1989) Tetrahedron Lett 30: 1889

    Article  CAS  Google Scholar 

  193. Pratt RF (1989) Science 246: 917

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Organique de Synthése, Université Catholique de Louvain, Place Louis Pasteur 1, B-1348, Louvain-La-Neuve, Belgium

    Jacqueline Marchand-Brynaert & Léon Ghosez

Authors
  1. Jacqueline Marchand-Brynaert
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Léon Ghosez
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut de Chimie des Substances Naturelles du C.N.R.S., Avenue de la Terrasse, F-91198, Gif-sur-Yvette Cedex, France

    G. Lukacs (Directeur de Recherche C.N.R.S.) (Directeur de Recherche C.N.R.S.)

  2. University of Tokyo, 7-3-1 Hongo, Bunkyo-ku Tokyo 113, Japan

    M. Ohno

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Marchand-Brynaert, J., Ghosez, L. (1990). Non β-Lactam Analogs of Penicillins and Cephalosporins. In: Lukacs, G., Ohno, M. (eds) Recent Progress in the Chemical Synthesis of Antibiotics. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75617-7_20

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-75617-7_20

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-75619-1

  • Online ISBN: 978-3-642-75617-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation