92003-63-9Relevant articles and documents
Synthesis, X-ray crystal structure and anti-tumor activity of calix[n]arene polyhydroxyamine derivatives
An, Lin,Han, Li-Li,Zheng, You-Guang,Peng, Xian-Na,Xue, Yun-Sheng,Gu, Xiao-Ke,Sun, Jing,Yan, Chao-Guo
, p. 21 - 30 (2016/08/01)
Calixarene-based compounds are highly effective therapeutic agents against cancer. This study aims to prepare a series of calix [n]arene (n?=?4, 6, 8) polyhydroxyamine derivatives (3a–3m) and to study their potential antitumor activities. The single crystal structure of calixs[4]arene derivative 3a was determined through X-ray diffraction. We assessed the ability of the prepared calix [n]arene polyhydroxyamine derivatives to induce cytotoxicity in six cancer cell lines by performing cancer cell growth inhibition assays. Results demonstrated that compounds 3a–3d achieved IC50values ranging from 1.6?μM to 11.3?μM. Among the different compounds, 3a and 3b exerted the strongest cytotoxic effect in inhibiting the growth of SKOV3 cells. In relation to the underlying mechanisms of cytotoxic effects, cell cycle analysis revealed that the exposure of SKOV3 cells to 3a induced cell cycle arrest in the G0/G1 phase, suggesting a reduction in DNA synthesis. Immunofluorescent staining indicated that the protein expression levels of caspase-3 and p53 in cells significantly increased, whereas that of Bcl-2 was effectively suppressed. Meanwhile, no significant changes in Bax were observed in SKOV3 cells. These results highlight that calixarene 3a can be further studied as a potential anticancer agent.
Synthesis, X-ray Crystal Structures, and Cation-Binding Properties of Alkyl Calixaryl Esters and Ketones, a New Family of Macrocyclic Molecular Receptors
Arnaud-Neu, Francoise,Collins, Elizabeth M.,Deasy, Mary,Ferguson, George,Harris, Stephen J.,at al.
, p. 8681 - 8691 (2007/10/02)
Calixarenes (N=4,6,8) have been converted into polyfunctional esters and ketones in a search for new macrocycles capable of showing ionophoric activity.Treatment with alkyl bromoacetates furnished the calixaryl acetate series, whereas chloroacetone-potassium iodide, phenacyl chloride, 1-adamantyl bromomethyl ketone, and bromopinacolone were used to make the calixaryl ketones series.The crystal structures of ethyl calixaryl acetate (7), methyl calixaryl acetate (13), ethyl calixaryl acetate (11), and calixaryl methyl ketone (20) have been determined.Thecrystals of 7 are triclinic, space group P, with two molecules in the unit cell of dimensions a = 12.434(2) Angstroem, b = 15.033(3) Angstroem, c = 17.286(4) Angstroem, α = 103.01(2) deg, β = 102.97(1) deg and γ = 94.68(1) deg.The crystals of 13 are monoclinic, space group C2/c, with eight molecules in the unit cell of dimensions a = 27.066(6) Angstroem, b = 21.392(6) Angstroem, c = 21.348(7) Angstroem, and β = 119.32(2) deg.The crystals of 11 are monoclinic, space group C2/c, with four molecules in the unit cell of dimensions a = 21.906(4) Angstroem, b = 11.805(2) Angstroem, c = 23.534(4) Angstroem, and β = 91.79(2) deg.The crystals of 20 are orthorhombic, space group Pbcn, with four molecules in the unit cell of dimensions a = 19.644(7) Angstroem, b = 12.712(3) Angstroem, and c = 22.115(7) Angstroem.Both 11 and 20 have crystallographically imposed 2-fold molecular axes.The analysis establishes that all three tetramer derivatives possess the cone conformation in the solid state where the pendant-functionalized side chains are mutually syn with respect to the calixarene substructure and are thus preorganized for ionreception.NMR measurements confirm the existence of the cone conformation for these tetramers in solution at room temperature.In contrast, the centrosymmetric hexamer ester 11 has three adjacent groups syn, but the inversion symmetry places the other three ester groups in the anti position on the opposite side of the macrocycle.Extraction studies with alkali metal picrates from aqueous solution into dichloromethane, transport studies with alkali metal thiocyanates through a dichloromethane membrane, and stability constant measurements with alkali metal salts by UV absorption spectroscopy in methanol and acetonitrile were used to assess the ionophoric activity of these calixarene derivatives.The tetramer esters and ketones display peak selectivity for the sodium ion, the tetraketones being generally more efficient binders than the tetraesters.The hexaester extracts K(1+) better than Na(1+) and displays a plateau selectivity after K(1+).The octamers are the least effective ionophores.The selectivities shown by the picrate extraction technique are broadly mirrored in the transport studies.Stability constants range from 2 to 6, ...
Synthesis, X-Ray Crystal Structures, and Cation Transfer Properties of Alkyl Calixaryl Acetates, a New Series of Molecular Receptors
McKervey, M. Anthony,Seward, Eileen M.,Ferguson, George,Ruhl, Barbara,Harris, Stephen J.
, p. 388 - 390 (2007/10/02)
Calix-, -, and -arenes have been converted into a series of alkyl acetates which show significant phase-transfer activity and selectivity towards alkali metal picrates; the X-ray crystal structures of two members of the series, (1b) and (2d), have been determined.
