Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Semiempirical Molecular Orbital Calculations of the Substituent Effects on Acylations of 3-Cephem Analogues

  • Chang Moon-Ho (Division of Applied Science, Korea Institute of Science and Technology) ;
  • Koh Hun-Yeong (Division of Applied Science, Korea Institute of Science and Technology) ;
  • Lee Jung-Chull (Division of Applied Science, Korea Institute of Science and Technology) ;
  • Lee Yoon Sup (Department of Chemistry and Center for Molecular Science, Korea Advanced Institute of Science and Technology)
  • Published : 1994.06.20
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Abstract

Semiempirical MO calculations are applied to estimate the substituent effects on acylations of the nonfused N-vinyl-2-amino $\beta-lactams$ having frameworks analogous to 3-cephems. The stabilization energy for the reaction intermediate of the nucleophilic attack by the hydroxide ion is selected as the reactivity index and calculated by AM1 and PM3 methods for the model $\beta-lactams$ with substituents at the C1 and N-vinyl terminal positions. The reactivities are larger for -SH connected to the C1 and strong $\pi-acceptors$ at the N-vinyl terminal implying the large reactivity for known active cephalosporins. Quantum chemical calculation of stabilization energy could be useful in correlating antibiotic activities of many compounds obtained as derivatives of a lead compound.

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References

  1. Chemistry and Biology of $\beta$-lactam Antibiotics v.1 Morin, R. B.;Gorman, M.
  2. Chem. Pharm. Bull. v.29 Kamiya, K.;Takamoto, M.;Wada, Y.;Nishikawa, M.
  3. J. Chem. Edu. v.53 Boyd, D. B.
  4. Int. J. Quantum. Chem. Biol. Symp. v.4 Boyd, D. B.
  5. J. Chem. Soc. Perkin Trans. v.1 Sakagami, K.;Tashiro, M.;Takeuchi, Y.;Hatanaka, M.
  6. J. Med. Chem. v.34 Jungheim, L. N.;Boyd, D. M.;Indelicato, J. M.;Pashini, C. E.;Preston, D. A.;Alborn, W. E.
  7. Kor. J. Med. Chem. v.3 Chang, M.-H.;Koh, H.-Y.;Kang, H.-Y.;Lee, J.-C.;Lee, Y. S.
  8. J. Med. Chem. v.18 Boyd, D. B.;Herman, R. B.;Presti, D. E.;Marsh, M. M.
  9. J. Med. Chem. v.17 Topp, W. C.;Christensen, B. G.
  10. QCPE Program No. 455, Ver. 6.0 QCPE
  11. J. Comp. -Aided Mol. Des. v.4 Stewart, J. J. P.
  12. J. Comp. Chem. v.10 Stewart, J. J. P.
  13. Gaussian 92 program Gaussian Inc.
  14. Chem-X Chemical Design Ltd.
  15. J. Mol. Struc. v.166 Sedano, E.;Ugalde, J. M.;Cossio, F. P.;Palomo, C.

Cited by

  1. ChemInform Abstract: Semiempirical Molecular Orbital Calculations of the Substituent Effects on Acylations of 3-Cephem Analogues. vol.26, pp.8, 1994, https://doi.org/10.1002/chin.199508270