1999
DOI: 10.1021/jm9806695
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Conformational and Quantitative Structure−Activity Relationship Study of Cytotoxic 2-Arylidenebenzocycloalkanones

Abstract: Various 2-arylideneindanones 1, 2-arylidenetetralones 2, and 2-arylidenebenzosuberones 3 were synthesized with the aim of determining the relative orientations of the two aryl rings which favored cytotoxicity. Molecular modeling of the unsubstituted compound in each series revealed differences in the spatial arrangements of the two aryl rings, and evaluation of these compounds against P388, L1210, Molt 4/C8, and CEM cells as well as a panel of human tumor cell lines indicated that in general the order of cytot… Show more

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Cited by 114 publications
(103 citation statements)
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References 25 publications
(31 reference statements)
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“…The compounds in series 1-5 were prepared by condensation between various aryl aldehydes and the appropriate ketones 13,14 . These molecules were shown by 1 H-NMR spectroscopy and in several cases by X-ray crystallography to adopt the E stereochemistry 13,14,16 .…”
Section: Resultsmentioning
confidence: 99%
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“…The compounds in series 1-5 were prepared by condensation between various aryl aldehydes and the appropriate ketones 13,14 . These molecules were shown by 1 H-NMR spectroscopy and in several cases by X-ray crystallography to adopt the E stereochemistry 13,14,16 .…”
Section: Resultsmentioning
confidence: 99%
“…These molecules were shown by 1 H-NMR spectroscopy and in several cases by X-ray crystallography to adopt the E stereochemistry 13,14,16 . The choice of aryl substituents was made on the basis of their differing electronic, hydrophobic and steric properties.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Among the naturally occurring chalcones and their synthetic analogues, several compounds displayed antineoplastic activity [2] [3]. Recently we have investigated in vitro antineoplastic activity of several synthetic chalcones and chalcone analogues [4]- [6]. (E)-2-(4'-methoxybenzylidene)-1-benzosuberone (4a) and (E)-2-(4'-dimethylaminobenzylidene)-1-benzosuberone (4c) (Figure 1) had the greatest tumor cytotoxicity of all studied molecules.…”
Section: Introductionmentioning
confidence: 99%
“…1 Specifically, (E)-2-benzylideneindan-1-one 1 has been shown to exhibit cytotoxic activity against murine P388 and L1210 leukaemic cells as well as human Molt 4/C8 and CEM Tlymphocytes. 2 Several methods for their preparation have been reported, the most classic involving as the first step the synthesis of indan-1-one moiety followed by an aldol reaction with the appropriate aldehydes. 3 Problems may be encountered with chemical methods such as incomplete transformation, moderate enantiomeric purity and the use of toxic reagents.…”
Section: Introductionmentioning
confidence: 99%