- Molecular dynamics simulation, synthesis and topoisomerase inhibitory actions of vanillin derivatives: a systematic computational structural integument
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A series of 4-hydroxy-3-methoxy benzaldehyde (vanillin) derivatives (3a–3r) was designed for the principle of Schiff base condensation with several individual sulfanilamide analogues. The inhibitory potencies of the designed compounds were evaluated through molecular docking simulation studies against the targets, breast cancer-topo isomerase-IIα and estrogen receptor-α; and the top scoring poses with higher binding energy were selected to assess the mode of binding and stability of each complex through molecular dynamics simulations. Compounds that remained stable in the active sites of the both target receptors through a number of strong H-bonds and hydrophobic contacts were selected. Based on the computational results, these selected compounds, 3b, 3e and 3f were synthesized and were followed up for structural elucidation attempts, by FT/ATR, 1H NMR and 13C NMR. From the experimental in vitro studies on 3b, 3e and 3f, the following remarkable activities against breast cancer cell line were done; IC50 values of 3b, 3e and 3f were noted, 6.7, 4.3 and 11 ng/mL, respectively. These newly synthesized compounds may be used as novel inhibitors of nuclear receptors with potential therapeutic applications in control of cancer. Communicated by Ramaswamy H. Sarma.
- Dehury, Budheswar,Padhy, Rabindra Nath,Paidesetty, Sudhir Kumar,Sahoo, Chita Ranjan,Sarathbabu, Subbarayan,Senthil Kumar, Nachimuthu
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- Vanillin esters in reactions with indan-1,3-dione
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2-Methoxy-4-(12-oxo-12H-benzo[f]indeno[1,2-b]quinolin-13-yl)phenyl esters of carboxylic acids were synthesized by the three component condensation of indan-1,3-dione, 2-naphthylamine, and O-acylvanillin. 2-Arylidenindan-1,3-diones formed during the reaction were isolated. Springer Science+Business Media, Inc. 2006.
- Kozlov,Basalaeva
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p. 1223 - 1228
(2008/09/21)
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- Preparative synthesis of vanillin and vanillal alkanoates
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Procedures for preparing vanillin and vanillal alkanoates were developed.
- Dikusar,Vyglazov,Moiseichuk,Zhukovskaya,Kozlov
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p. 120 - 124
(2007/10/03)
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- Vanilline alkanoates in the synthesis of hexahydrobenzacridine and octahydroxanthene derivatives
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Cascade heterocyclization of 1,3-cyclohexanedione and dimedone with 2-naphthylamine and vanilline esters gave derivatives of 2-methoxy-4-(alkyl-11- oxo-7,8,9,10,11,12-hexahydrobenz[a]acridin-12-yl)- and 2-methoxy-4-(alkyl-1,8- dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl esters of aliphatic (C1- C4 ) carboxylic acids. 2005 Pleiades Publishing, Inc.
- Kozlov,Basalaeva
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p. 617 - 621
(2007/10/03)
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- Vanillin esters of aliphatic acids in the synthesis of 4,7-phenanthroline derivatives
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Condensation of vanillin esters of aliphatic acids with 6-aminoquinoline and cyclic c-diketones (1,3-cyclohexanedione and dimedone) afforded new 2-methoxy-4-(11-oxo-7,8,9,10,11,12-hexahydrobenzo[b][4,7]phenanthrolin-12-yl) phenyl esters of carboxylic acids.
- Kozlov,Gusak,Tereshko,Dikusar
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p. 705 - 710
(2007/10/03)
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- 1'-Hydroxyeugenol- and coniferyl alcohol derivatives as effective inhibitors of 5-lipoxygenase and Cu(2+)-mediated low density lipoprotein oxidation. Evidence for a dual mechanism.
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1'-Hydroxyeugenol- and epoxy-Z-coniferyl alcohol esters from Coreopsis species as well as synthetic derivatives of these natural compounds were examined as lipoxygenase inhibitors and as LDL (low density lipoprotein)-stabilizing agents. Most of the compounds displayed inhibitory activity on the formation of leukotrienes (LTB4 and LTC4) in a cellular (RBL-1 cells) assay as well as in a cell-free 5-lipoxygenase assay at concentrations of 4-24 mumol/l. No effect of selected compounds was observed on mammalian lipoxygenases with other specificity (12- and 15-lipoxygenase). The more lipophilic derivatives also effectively reduced Cu(2+)-mediated oxidation of LDL. The findings are discussed on the base of structure-activity relationships.
- Deigner,Wolf,Ohlenmacher,Reichling
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p. 956 - 961
(2007/10/02)
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