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Scientific article
English

Structure-activity relationship between the 3D distribution of the electrophilicity of sugar derivatives and their cytotoxic and antiviral properties

Contributors

Ricca, Alessandra; Tronchet, Jean Marcel Julien; Weber, Jacques

Published in

Journal of computer-aided molecular design, vol. 6, no. 18, 541

Publication date

1992

Abstract

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.

Keywords

  • Structure
  • Property correlations
  • Reactivity index
  • Electrophilic reactivity
  • Michael acceptor sugars

UNIGE affiliation entities

UNIGE research groups

Citation (ISO format)

RICCA, Alessandra, TRONCHET, Jean Marcel Julien, WEBER, Jacques. Structure-activity relationship between the 3D distribution of the electrophilicity of sugar derivatives and their cytotoxic and antiviral properties. In: Journal of computer-aided molecular design, 1992, vol. 6, n° 18, p. 541. doi: 10.1007/BF00126213

Identifiers

Journal ISSN

0920-654X
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Technical informations

Creation

21/09/2009 16:09:59

First validation

21/09/2009 16:09:59

Update

14/03/2023 15:12:29

Status update

14/03/2023 15:12:29

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