A structure-activity relationship study of lapachol and some derivatives of 1,4-naphthoquinones against carcinosarcoma Walker 256

dc.creatorSubramanian, S
dc.creatorFerreira, MMC
dc.creatorTrsic, M
dc.date1998
dc.dateFEB
dc.date2014-12-02T16:28:20Z
dc.date2015-11-26T16:36:27Z
dc.date2014-12-02T16:28:20Z
dc.date2015-11-26T16:36:27Z
dc.date.accessioned2018-03-28T23:19:12Z
dc.date.available2018-03-28T23:19:12Z
dc.identifierStructural Chemistry. Plenum Publ Corp, v. 9, n. 1, n. 47, n. 57, 1998.
dc.identifier1040-0400
dc.identifierWOS:000071416000008
dc.identifier10.1023/A:1022487632133
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/53841
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/53841
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/53841
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1271821
dc.descriptionAM1 semiempirical molecular orbital calculations were carried out on lapachol and several derivatives of 1,4-naphthoquinone in order to investigate possible relationships between electronic structural parameters and activity against carcinosarcoma Walker 256 (W256). It was found that, among the calculated electronic indices, that the HOMO (highest occupied molecular orbital) coefficients for carbon atoms of the side-chain double bond have a significant influence in the activity, while the LUMO (lowest unoccupied molecular orbitals) apparently have no importance. Exploratory data analysis through hierarchical cluster (HCA) and principal component analysis (PCA) showed a clear separation of the active compounds from the inactive ones. The activity against W256 probably involves a mechanism wherein the quinone acts as a reducing agent through the participation of the pi-electrons of the side-chain double bond. A classification study with respect to structure-activity using KNN (K-nearest neighbors) and SIMCA (soft independent modeling of class analogy), two established chemometric methods of pattern recognition, have been used to predict activity for a series of lapachol derivatives.
dc.description9
dc.description1
dc.description47
dc.description57
dc.languageen
dc.publisherPlenum Publ Corp
dc.publisherNew York
dc.publisherEUA
dc.relationStructural Chemistry
dc.relationStruct. Chem.
dc.rightsfechado
dc.sourceWeb of Science
dc.subjectMNDO-AM1-SCF-MO
dc.subjectLapachel
dc.subjectPCA-HCA-KNN-SIMCA
dc.subjectPattern-recognition
dc.subjectQuinones
dc.titleA structure-activity relationship study of lapachol and some derivatives of 1,4-naphthoquinones against carcinosarcoma Walker 256
dc.typeArtículos de revistas


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