Diethyl [(9-anthr­yl)(4-methyl­anilino)meth­yl]phospho­nate

The title compound, C26H28NO3P, crystallized with two independent mol­ecules in the asymmetric unit. The structural features (bond lengths and angles) of the two mol­ecules are almost identical. The inter­planar angle between the anthracene and toluidine rings is similar in the two mol­ecules, with values of 82.92 (5) and 80.70 (5)°. In the crystal, both molecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds. Three of the four ethyl groups are disordered over two sets of sites, the major components having occupancies of 0.748 (15), 0.77 (4) and 0.518 (19)

rac-Dimethyl [(9-anthr­yl)(4-methyl­anilino)meth­yl]phospho­nate

The title compound, C24H24NO3P, crystallizes as a racemate with two mol­ecules in the asymmetric unit. The structural features (bond lengths and angles) of the two mol­ecules are almost identical. The dihedral angle between the anthracene and toluidine rings is similar in the two mol­ecules, with values of 48.36 (9) and 51.15 (9)°. The methyl groups of one of the meth­oxy groups in one mol­ecule is disordered over two sets of sites, the major component having a site occupancy of 0.636 (3). In the crystal, both molecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds

Synthesis of octa(1,1,3,3-tetramethylbutyl)octakis (dimethylphosphinoylmethyleneoxy)calix[8]arene and its application in the synergistic solvent extraction and separation of lanthanoids

A new lower rim substituted calix[8]arene bearing eight phosphine oxide moieties has been synthesized. The structure of 5,11,17,23,29,35,41,47-octa(1,1,3,3-tetramethylbutyl)-49,50,51,52,53,54,55,56-octakis(dimethylphosphinoylmethyleneoxy)calix[8]arene (S) was identified and confirmed by elemental analysis, IR-, H-1, C-13 and P-31-{H-1} NMR spectroscopy as well as by ES-mass spectrometry

In vitro antitumour activity, safety testing and subcellular distribution of two poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s in Ehrlich ascites carcinoma and BALB/c 3T3 cell culture systems

Two polyphosphoesters containing anthracene-derived aminophosphonate and hydrophilic H-phosphonate repeating units, poly[oxyethylene(aminophosphonate-co-H-phosphonate)]s (1 and 2), were tested for the in vitro antitumour activity on cell cultures derived from ascitic form of Ehrlich mammary adenocarcinoma by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT)-dye reduction assay. The in vitro safety testing of the copolymers was performed by BALB/c 3T3 neutral red uptake assay. A study on their uptake and subcellular distribution in non-tumourigenic and tumour cells was performed by means of fluorescence microscopy. Both copolymers showed significant antitumour activity towards Ehrlich ascites carcinoma (EAC) cells. However, the in vitro safety testing revealed significant toxicity of polymer 2 to BALB/c 3T3 mouse embryo cells. In contrast, polymer 1 showed complete absence of cytotoxicity to BALB/c 3T3 cells. The fluorescent studies showed that the substances were diffusely distributed in the cytoplasm in both cell culture systems. As opposed to BALB/c 3T3 cells, in EAC cells, intense fluorescent signal was observed in the nuclei and in the perinuclear region. The tested polyphosphoesters are expected to act under physiological conditions as prodrugs of aminophosphonates

Synthesis and characterization of partially substituted at lower rim phosphorus containing calix(4)arenes

The synthesis and characterization of several new phosphorus-containing partially lower rim substituted derivatives of 5,11,17,23-tetra(t-butyl) calix(4)arene (1) and 5,11,17,23-tetra(t-octyl)calix(4)arene (II), namely 5,11,17,23-tetra(t-butyl)-25,27-dihydroxy-26,28-bis(diphenylphosphinoyl-oxy) calix(4)arene (IV); 5,11,17,23-tetra(t-butyl)-25-hydroxy-26,27,28-tris(tetramethyldiamido- phosphinoyl-oxy) calix(4)arene (Vb); 5,11,17,23-tetra(t-butyl)-25,27-dihydroxy-26,28-bis(dimethyl-phosphinoyl- methoxy) calix(4)arene (VI); 5,11,17,23-tetra (t-octyl)25,27-dihydroxy-26,28-bis(dimethyl-phosphinoyl-methoxy) calix(4)arene (VII) are reported. The structure of the synthesized calix(4)arene derivatives are identified and confirmed by elemental analysis, IR, H-1, C-13, P-31(H-1) NMR spectroscopy and mass spectrometry as and X-ray crystallographic analysis of 5,11,17,23-tetra(t-butyl)25,27-dihydroxy-26,28-bis(dimethyl-phosphinoyl-methoxy) calix(4)arene VI. According to the NMR spectra, all calix(4)arenes are in cone conformation

Aggregation behavior and in vitro biocompatibility study of octopus-shaped macromolecules based on tert-butylcalix[4]arenes

A series of products based on tert-butylcalix[4]arene have been synthesized by anionic polymerization of ethylene oxide. The resulting products are amphiphilic octopus-shaped macromolecules, consisting of a hydrophobic calix[4]arene core and four arms of hydrophilic poly(ethylene oxide) chains. In aqueous solutions the polyoxyethylated tert-butylcalix[4]arenes were found to self-associate above certain CMC determined by dye solubilization technique. The light scattering study reveals that the polyoxyethylated tert-butylcalix[4]arenes form aggregates of narrow size distribution and hydrodynamic diameters ranging from about 155 to 245 nm and aggregation numbers from tens to hundreds macromolecules per particle depending on the degree of polymerization of the PEO chains. An in vitro biocompatibility study showed that the tested compounds are practically devoid of intrinsic cytotoxic and hemolytic effects and moreover they failed to modulate the mitogen-induced interleukin-2 release from the human T-lymphocyte cell line Jurkat E6-1. Taken together the excellent in vitro biocompatibility profile and the favorable physicochemical characteristics of the tested polyoxyethylated calix[4]arenes give us reason to consider them as promising for further evaluation as drug delivery platforms