QSAR for cycloaliphatic alcohols with qualitatively defined sandalwood odour characteristics

D. I. Hadaruga, S. Muresan, C. Bologa, A. Chiriac, Z. Simon, Luciana Cofar, G. Naray-Szabo

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Abstract

QSAR's are set up for a series of up to 53 cycloaliphatic alcohols with qualitatively defined sandalwood odour characteristics: i-inactive, w-weak, s-strong, and vs-very strong. 'Central' values (0, 1, 2, and 3) were attached to these qualitative characteristics, as well as intervals (< 0.5; 0.5-1.5; 1.5-2.5; > 2.5). The superposition procedure of the MTD method was used to define the probable active conformation. Conformational energies and log P(oct) values were also calculated using HyperChem-2 and Chemicalc-2. A correlational equations were set up using δ, D and D2-with δ = 1 for OH groups in favourable position and D-the distance between the gravity centre of the hydrophobic moiety and the osmophoric OH-group. The MTD method was used only for a series of N = 15 rigid molecules, because a too large number of vertices for the whole series appear. Eighter central values or intervals were used as biologic activities. The δ, D and D2-equations set up for N = 31 molecules allow a good classification of the training set and also of the rest of molecules, considered as test set. An osmophoric receptor with a hydrophylic part (2 or 3 OH-groups) and a relatively large hydrophobic pocket is suggested, which produces also some steric misfit with regard to these molecules.

Original languageEnglish
Pages (from-to)253-261
Number of pages9
JournalQuantitative Structure-Activity Relationships
Volume18
Issue number3
DOIs
Publication statusPublished - Jul 1999

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Keywords

  • MLR
  • MTD
  • Osmophore
  • Sandalwood odour

ASJC Scopus subject areas

  • Pharmacology

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