caa a22 4500 469053313 CHVBK 20180323132836.0 cr unu---uuuuu 170328e19921201xx s 000 0 eng 10.1007/BF00126213 doi (NATIONALLICENCE)springer-10.1007/BF00126213 Structure-activity relationship between the 3D distribution of the electrophilicity of sugar derivatives and their cytotoxic and antiviral properties [Elektronische Daten] [Alessandra Ricca, Jean Tronchet, Jacques Weber] Summary: The cytotoxic activities of a series of sugar derivatives bearing electrophilic groups (1-cyanovinyl, 4-cyanochromen-2-yl and 3-nitrochromen-2-yl) have been correlated with their electrophilic properties. To this end, an electrophilic index was defined as an isovalue surface where the interaction energy with an incoming model nucelophile (H−) was equal to a predefined value. This index, calculated from extended Hückel wave functions, allows one to quantify the electrophilic character of the substrates and to describe its spatial localization within the molecular volume (at Michael acceptor sites or on other parts of the molecules). Only sugars for which Michael acceptor reactivity was predicted were retained, and they were subdivided into two groups: those showing antiviral activity against a retrovirus and those devoid of such activity. Under these conditions, good correlations between cytotoxic activity and electrophilic reactivity-positive for the first group, negative for the second-were found. In addition, the ratio electrophilicity/sum of the absolute value of the dipole plus its projection along the principal axis of inertia, Z, of the molecule allows one to predict to which of these groups a sugar derivative belongs. ESCOM Science Publishers B.V, 1992 Structure-property correlations nationallicence Reactivity index nationallicence Electrophilic reactivity nationallicence Michael acceptor sugars nationallicence Ricca Alessandra Department of Pharmaceutical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut Tronchet Jean Department of Pharmaceutical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut Weber Jacques Department of Physical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut Journal of Computer-Aided Molecular Design Kluwer Academic Publishers 6/6(1992-12-01), 541-552 0920-654X 6:6<541 1992 6 10822 https://doi.org/10.1007/BF00126213 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00126213 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Ricca Alessandra Department of Pharmaceutical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut NATIONALLICENCE 700 1- Tronchet Jean Department of Pharmaceutical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut NATIONALLICENCE 700 1- Weber Jacques Department of Physical Chemistry, University of Geneva, 30 quai E. Ansermet, 1211, Geneva 4, Switzerland aut NATIONALLICENCE 773 0- Journal of Computer-Aided Molecular Design Kluwer Academic Publishers 6/6(1992-12-01), 541-552 0920-654X 6:6<541 1992 6 10822 Metadata rights reserved Springer special CC-BY-NC licence nationallicence SWISSBIB 214149595 BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer