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white powder

Upstream product

• 68971-82-4 5,11,17,23,29,35,41,47-octakis(tert-butyl)-49,50,51,52,53,54,55,56-octakis(hydroxy)calix[8]arene 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis, X-ray crystal structure and anti-tumor activity of calix[n]arene polyhydroxyamine derivatives

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.

Novel synthesis of calix[n]arene amidoazobenzene derivatives

A series of calix[n]arenas and calix[4]resorciarenes containing azo chromophores on the lower rim were synthesised with two routes. The first direct route involved alkylating calixarenes with 4-chloroacetoaminoazobenzene. The second indirect route was by acylating 4-aminoazobenzene with calix[n]arylacetyl chloride. Their extracting abilities for transition metal ions were tested.

Synthesis, X-ray Crystal Structures, and Cation-Binding Properties of Alkyl Calixaryl Esters and Ketones, a New Family of Macrocyclic Molecular Receptors

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, ...

New Metal Cation-Selective Ionophores Derived from Calixarenes: Their Syntheses and Ion-Binding Properties

Various derivatives (ethoxycarbonylmethyl, carboxymethyl, and ethoxyethyl, etc.) of calixarene, calixarene, and calixarene have been synthesized and their ion-binding properties investigated by solvent extraction, ion-transport through liquid membranes, and u.v. spectroscopy.The extraction of various metal ions (as picrate salts) from the aqueous phase into dichloromethane by the calixarene derivatives showed that the ethoxycarbonylmethyl derivatives exhibited markedly increased extraction efficiency compared with their unsubstituted phenol analogues, and the efficiency was in general comparable to those of crown ethers.The most notable feature was the selectivities exhibited by their ethoxycarbonylmethyl derivatives; calixarene for Na(+), calixarene for Cs(+), and calixarene for K(+).A liquid membrane study with a water-chloroform-water system also indicated that the ion-transport efficiencies exhibited by calixarenes were found to be in accordance with their extraction abilities, confirming the strong participation of the ester carbonyl oxygen in this function.However, the ester derivative of calixarene was an exception in that inefficient carrier activity was observed in spite of high extraction efficiency.The pronounced Cs(+) selectivity exhibited by the calixarene ester was further confirmed by the changes in the u.v. spectrum of the ester from 277 and 270 nm to 275 and 267 nm upon interaction with Cs(+) ion in methanol.

Synthesis, X-Ray Crystal Structures, and Cation Transfer Properties of Alkyl Calixaryl Acetates, a New Series of Molecular Receptors

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.

NEW METAL CATION-SELECTIVE IONOPHORES DERIVED FROM CALIXARENES

Ethoxycarbomethyl derivatives of calixarene and calixarene prepared by the reaction of bromoacetic acid ester with the calixarenes exhibited distinct size-selectivity in their ion-extracting behaviors towards Cs+ and K+ ions.