Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides.

Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated selenoindirubins were previously reported, but without quantities, yields, scales, experimental details and spectroscopic data. In addition, the work could, in our hands, not be reproduced to prepare pure products. The present paper includes an optimized procedure for the synthesis of selenoindirubins and their complete characterization. Both selenoindirubins and selenoindirubin-N-glycosides showed antiproliferative activity in lung cancer cell lines. In melanoma cells, antiproliferative effects were further accompanied by induced apoptosis in combination with the death ligand TRAIL.

Crystal structure of (E)-pent-2-enoic acid.

The mol-ecule of the title compound, C5H8O2, a low-melting α,ß-unsaturated carb-oxy-lic acid, is essentially planar [maximum displacement = 0.0239 (13) Å]. In the crystal, mol-ecules are linked into centrosymmetric dimers via pairs of O-H⋯O hydrogen bonds.

Crystal structure of (E)-hex-2-enoic acid.

The crystal structure of the title compound, C6H10O2, an α,ß-unsaturated carb-oxy-lic acid, displays carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds. The packing is characterized by layers of acid dimers. All the non-H atoms of the (E)-hex-2-enoic acid mol-ecule lie almost in the same plane (r.m.s. deviation for the non-H atoms = 0.018 Å).

Crystal structure of (E)-undec-2-enoic acid.

In the mol-ecule of the title low-melting α,ß-unsaturated carb-oxy-lic acid, C11H20O2, the least-squares mean line through the octyl chain forms an angle of 60.10 (13)° with the normal to plane of the acrylic acid fragment (r.m.s. deviation = 0.008 Å). In the crystal, centrosymmetrically related mol-ecules are linked by pairs of O-H⋯O hydrogen bonds into dimers, forming layers parallel to the (041) plane.

Crystal structure of (E)-dodec-2-enoic acid.

The crystal structure of (E)-dodec-2-enoic acid, C12H22O2, an α,ß-unsaturated carb-oxy-lic acid with a melting point (295 K) near room temperature, is characterized by carb-oxy-lic acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds. The carb-oxy-lic acid group and the following three carbon atoms of the chain of the (E)-dodec-2-enoic acid mol-ecule lie almost in one plane (r.m.s. deviation for the four C atoms and two O atoms = 0.012 Å), whereas the remaining carbon atoms of the hydro-carbon chain adopt a nearly fully staggered conformation [moduli of torsion angles vary from 174.01 (13) to 179.97 (13)°].