Numerical descriptors for the characterization of chiral compounds and their applications in modeling biological and toxicological activities

Ramanathan Natarajan, Subhash C. Basak

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Due to the advancement in chiral synthesis and separation technology and the new regulatory policies for chiral pharmaceuticals several manufacturers are replacing the previously marketed racemate chemicals with single enantiomeric products, the so called chiral switch. Though 25% of agrochemicals are chiral in nature, most of them are sold as racemates or enantiomer enriched products. Chiral pesticides and some of the pharmaceuticals reach the human food chain as pollutants. Stereoisomers (enantiomers and diastereoisomers) not only differ from one another in their medicinal effects, but also in their phramacokinectic (adsorption, distribution, biotransformation and excretion) profiles and toxico-logical properties. Several recent attempts have been reported in the literature on developing mathematical models to predict the properties of chiral molecules from structure and such methods utilized numerical characterization. A comparison of different mathematical approaches on the numerical characterization of molecules with chiral center(s) and a brief background on the importance of stereochemistry in pharmacology, agrochemistry and environmental toxicology is presented.

Original languageEnglish (US)
Pages (from-to)771-787
Number of pages17
JournalCurrent topics in medicinal chemistry
Volume11
Issue number7
DOIs
StatePublished - Apr 1 2011

Keywords

  • Chirality
  • Chirality index
  • Chirality measures
  • Diastereoisomers
  • Enantiomers
  • Quantitative structure-activity relationship

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