Computational Study of Pharmacophores: β-Lactams
Computational Study of Pharmacophores: β-Lactams
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药效团的计算研究：β-内酰胺
DOI：
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发表时间：
2006
期刊：
影响因子：
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通讯作者：
P. J. Chua
中科院分区：
文献类型：
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作者：
I. Novák;P. J. Chua
采用高水平从头计算方法研究了β-内酰胺类抗生素中关键药效团——双环内酰胺类（penams, penems, cephams, cepphems）的热化学性质。由于在实验中难以测量和区分四元内酰胺环的酰胺共振（ARE）和环应变（RSE）的大小，因此对这些值的估计给予了特别的关注。环应变失稳效应大于酰胺共振引起的稳定效应。然而，在头孢烯中，由于β-内酰胺环菌株的作用，酰胺共振稳定性略高于不稳定性。
The thermochemistry of bicyclic lactams (penams, penems, cephams, cephems), which are key pharmacophores in β-lactam antibiotics, has been investigated by high-level ab initio methods. Particular attention has been paid to estimating magnitudes of amide resonance (ARE) and ring strain (RSE) in the four-member lactam ring because these quantities are difficult to measure and distinguish experimentally. The ring strain destabilization effect is greater than the stabilization arising from amide resonance. However, in cephemes the amide resonance stabilization slightly exceeds destabilization due to the β-lactam ring strain.