A Novel Triterpene Saponin from Gypsophila capillaris

A novel C-28 tetraglycoside of quillaic acid (1) has been isolated from Gypsophila capillaris. The structure was elucidated by 1 D NMR (NOE difference, DEPT, selective13C{1H} INEPT), 2D NMR (1H,1H and1H,13C COSY,1H,1H,1H RELAY, ROESY and TOCSY) and other spectroscopic and chromatographic evidences. Conformational dynamics within the tetrasaccharide part were estimated from NOE responses and ROESY peaks. © 1995 Verlag der Zeitschrift für Naturforschung. All rights reserved

N-{[(4-Nitrophenyl)amino]methyl}benzamide

We report the synthesis of N-{[(4-nitrophenyl)amino]methyl}benzamide from (benzamidomethyl)triethylammonium chloride and 4-nitroaniline in aqueous media. The structure of the newly synthesized compound was characterized on the basis of 1H-NMR, 13C-NMR and FTIR spectroscopy

1,1,2,2-Tetrakis[(benzoylamino)methyl]hydrazine

We report herein the synthesis of 1,1,2,2-tetrakis[(benzoylamino)methyl]-hydrazine from (benzamidomethyl)triethylammonium chloride and hydrazine monohydrate in the presence of triethylamine in ethanol/aqueous media. The structure of the newly synthesized compound was characterized on the basis of 1H-NMR, 13C-NMR, IR and mass spectral data

3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinylidene]chroman-2,4-dione

In the title compound, C16H15N3O4, the dihedral angle between the chromane and isoxazole rings [r.m.s. deviations = 0.042 and 0.007 Å, respectively] is 20.33 (12)°. The molecular geometry is stabilized by an intramolecular N—H...O hydrogen bond. In the crystal, N—H...O hydrogen bonds generate chains along the c-axis direction. The crystal studied was a non-morohedral twin

Hydrazinyldiene-chroman-2,4-diones in inducing growth arrest and apoptosis in breast cancer cells: Synergism with doxorubicin and correlation with physicochemical properties

This study evaluates the effects of previously synthesized hydrazinyldiene-chroman-2,4-diones on cell proliferation and apoptosis, cell cycle distribution and migration capacity of MCF-7 breast cancer cells in synergy with doxorubicin. Physicochemical properties of the synthesized compounds were correlated with their structure and activity. Significant cell viability decrease in comparison with the effect of doxorubicin alone and the reference 4-hydroxycoumarin was observed when combination treatment comprising doxorubicin and the title compounds was applied. Synergistic effect with doxorubicin was also observed in down-regulation of phospho-Thr308Akt levels, confirming reduced proliferation and increased apoptosis. Combined treatment increased the percentage of cells arrested at the G2/M stage. Additive inhibition of cell migration was also observed, pointing to the possibility of reducing the risk of metastases. With their solubility profile and log D7.4, all the synthesized compounds follow Lipinski’s rule of five for good permeability (absorption) potential

Stereochemical Studies of some 12a-Substituted Rotenoid Derivatives

The absolute configuration at 6a and 12a positions as well as the conformation of rings B and C of some cis fused 12a-substituted (OH, CH2OH, CH2OCOR’) synthetic derivatives of natural rotenoids, rotenone and amor- phigenin, are discussed on the basis of \u27H NMR, CD and molecular mechanics studies. The CD Cotton effects above 300 nm of all 12a-substituted derivatives, compared with those of the parent natural rotenoids, show an unexpected sign inversion and cannot be used for reliable configurational assignment. This has been achieved in a nonempirical way by application of the exdton chirality method

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

The study highlights the current progress in the development of coumarin scaffolds for drug discovery as novel anticancer agents in metastatic breast cancer. Eight compounds, combining the coumarin core and five membered heterocycles (isoxazoles and thiazoles) in hydrazinyldiene- -chroman-2,4-diones, were characterized in terms of a potential antiproliferative effect on bone (SCP1833) and lung (SCP4175) metastatic breast cancer cell lines using the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide assay. Cell viability was evaluated after 48 and 72 h of treatment and the 50 % inhibitory concentrations were determined. The results demonstrated dose- and time-dependent activity, with the most potent molecules having a thiazole moiety, without or with additional methyl group(s) attached to the carbon(s) at position(s) 5 and/or 4 in the thiazole ring. These molecules possessed significantly higher potency against both test cell lines compared to 4-hydroxycoumari

Potential antiproliferative effect of isoxazolo- and thiazolo coumarin derivatives on breast cancer mediated bone and lung metastases

The study highlights the current progress in the development of coumarin scaffolds for drug discovery as novel anticancer agents in metastatic breast cancer. Eight compounds, combining the coumarin core and five membered heterocycles (isoxazoles and thiazoles) in hydrazinyldiene- -chroman-2,4-diones, were characterized in terms of a potential antiproliferative effect on bone (SCP1833) and lung (SCP4175) metastatic breast cancer cell lines using the 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide assay. Cell viability was evaluated after 48 and 72 h of treatment and the 50 % inhibitory concentrations were determined. The results demonstrated dose- and time-dependent activity, with the most potent molecules having a thiazole moiety, without or with additional methyl group(s) attached to the carbon(s) at position(s) 5 and/or 4 in the thiazole ring. These molecules possessed significantly higher potency against both test cell lines compared to 4-hydroxycoumari

[(3-Chlorobenzamido)methyl]triethylammonium Chloride

We report the synthesis of [(3-chlorobenzamido)methyl]triethylammonium chloride in a reaction of N-(chloromethyl)-3-chlorobenzamide and triethylamine in dry acetone. The structure of the newly synthesized compound was characterized with 1H-NMR, 13C-NMR, FTIR and Mass spectroscopy