The development of 3D-QSAR study and recursive partitioning of heterocyclic quinone derivatives with antifungal activity

Su Young Choi, Jae Hong Shin, Chung Kyu Ryu, Ky Youb Nam, Kyoung Tai No, Hea Young Park Choo

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22 Citations (Scopus)


It was reported that some 1,4-quinone derivatives such as 6-(N-arylamino)-7-chloro/6,7-bis[S-(aryl)thio]-5,8-quinolinedione and 6-arylthio-/5,6-arylamino-4,7-dioxobenzothiazoles have antifungal effects. To understand the structural basis for antifungal activity and guide in the design of more potent agents, we performed three-dimensional quantitative structure-activity relationship studies for a series of compounds using comparative molecular field analysis (CoMFA). The MIC values of 1,4-quinone derivatives on Aspergillus niger exhibited a strong correlation with steric and electrostatic factors of the 3D structure of molecules. The statistical results of the training set, cross-validated q2 (0.683) and conventional r2 (0.877) values, gave reliability to the prediction of inhibitory activity of a series of compounds. We also performed recursive partitioning (RP) analysis, used for the classification of molecules with activity using CART methods. Physicochemical, structural, and topological connectivity indices and E-state key descriptors were used for obtaining the decision tree models. The decision tree could classify the inhibitory activity of 1,4-quinone derivatives and its essential descriptors were S_aaN, Hbond donor, and Kappa-3.

Original languageEnglish
Pages (from-to)1608-1617
Number of pages10
JournalBioorganic and Medicinal Chemistry
Issue number5
Publication statusPublished - 2006 Mar 1

Bibliographical note

Funding Information:
This work was supported by the grant from Research Institute of Pharmaceutical Science in Ewha Womans University and Vision 21 Program from Korea Institute of Science and Technology.

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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