2002
DOI: 10.1002/chin.200225080
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ChemInform Abstract: Cytotoxic‐Antineoplastic Activity of Hydroquinone Derivatives.

Abstract: -080Cytotoxic-Antineoplastic Activity of Hydroquinone Derivatives.Several new myrcenylhydroquinone derivatives [cf. (II), (VI), and (VIII)] are synthesized and evaluated for their cytotoxic activity against three neoplastic cell line cultures.

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Cited by 3 publications
(4 citation statements)
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“…This would show the relevance of the planar naphthalenic group for the cytotoxic–antineoplastic activity, probably due to which it would allow a better intercalating association when they act as non‐covalent binders of DNA . In spite of the fact that the amino acid moiety does not significantly modify the bioactivity previously reported for naphthohydroquinones , it is interesting to note that the GI 50 values of compounds 4a – 8a against MCF‐7 breast cancer cells are very close to that of the standard drug doxorubicin and even slightly better for the phenylalanine derivative 6a . Furthermore, compounds 4a – 8a are more cytotoxic than several conjugates reported in the literature such as platinum complexes of enantiomerically pure α‐trifluoromethyl alanine , 1,4‐bis(2‐aminoethylamino)anthraquinone–, ametantrone–, and mitoxantrone–amino acid conjugates and more than naphthalimide–leucine conjugates against A‐549 and/or MCF‐7 cells. In the group of purine–naphthohydroquinone conjugates 10 – 13 , the fully aromatized compounds 10a – 13a (GI 50 2.9–8.7 μM) also showed higher cytotoxicity than the corresponding 5,8‐dihydro‐ ( 10b – 13b ) or 5,6,7,8‐tetrahydro‐ ( 10c – 13c ) derivatives against A‐549 or HT‐29 cultured cells.…”
Section: Resultsmentioning
confidence: 81%
See 1 more Smart Citation
“…This would show the relevance of the planar naphthalenic group for the cytotoxic–antineoplastic activity, probably due to which it would allow a better intercalating association when they act as non‐covalent binders of DNA . In spite of the fact that the amino acid moiety does not significantly modify the bioactivity previously reported for naphthohydroquinones , it is interesting to note that the GI 50 values of compounds 4a – 8a against MCF‐7 breast cancer cells are very close to that of the standard drug doxorubicin and even slightly better for the phenylalanine derivative 6a . Furthermore, compounds 4a – 8a are more cytotoxic than several conjugates reported in the literature such as platinum complexes of enantiomerically pure α‐trifluoromethyl alanine , 1,4‐bis(2‐aminoethylamino)anthraquinone–, ametantrone–, and mitoxantrone–amino acid conjugates and more than naphthalimide–leucine conjugates against A‐549 and/or MCF‐7 cells. In the group of purine–naphthohydroquinone conjugates 10 – 13 , the fully aromatized compounds 10a – 13a (GI 50 2.9–8.7 μM) also showed higher cytotoxicity than the corresponding 5,8‐dihydro‐ ( 10b – 13b ) or 5,6,7,8‐tetrahydro‐ ( 10c – 13c ) derivatives against A‐549 or HT‐29 cultured cells.…”
Section: Resultsmentioning
confidence: 81%
“…In previous works, we reported on the syntheses and cytotoxicity evaluation for a number of prenylnaphthoquinones (hydroquinones) and derivatives obtained through Diels–Alder cycloaddition from myrcene and 1,2‐ or 1,4‐benzoquinones. Those previous series of compounds displayed cytotoxicity GI 50 values in the micromolar or lower range against several neoplastic cell lines and, in general, resulted more potent than avarol and avarone (3–6 μM), two meroterpenoids of marine origin, and taken as comparative references in our studies .…”
Section: Introductionmentioning
confidence: 82%
“…Aldehydes 1a -c were prepared by previously reported procedures [29]. The IR spectra were recorded on a Perkin Elmer FT IR 1600 spectrophotometer (Perkin Elmer, USA) as a film over NaCl discs.…”
Section: Experimental Chemistrymentioning
confidence: 99%
“…[1][2][3][4][5][6] Among the rich variety of natural prenylated molecules, chromane and chromene derivatives, with an extra pyrano or dihydropyrano ring, represent a family of compounds endowed with most interesting properties. 7 All these molecules are generally characterized by low cellular toxicity and good membrane permeability, properties that make them ideal drug template compounds.…”
Section: Introductionmentioning
confidence: 99%