4-Des-oxy-4β-[(5-meth-oxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate

Abstract

The main mol-ecule of the title solvate, C(33)H(30)N(2)O(10)·CH(3)OH, is a new anti-tumor agent, which shows cytotoxicity against MDR cancer cell lines. It has been synthesized by coupling 4β-amino-podophyllotoxin with (5-meth-oxy-1H-indol-3-yl)glyoxyl chloride and structurally characterized. There are two crystallographically independent mol-ecules in the asymmetric unit, which differ in the dihedral angles between the aromatic rings. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the benzene ring of the 5-meth-oxy-1H-indole are 85.08 (3) and 76.88 (3)° and reflect the main conformational difference between the two independent mol-ecules. The asymmetric unit is completed with two methanol solvent mol-ecules, one of which is disordered over two positions, with occupancies close to 0.5.

Fig. 1.

The molecular structure of the main molecules, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The crystal is a methanol solvate, with a 1:1 composition with respect to the main molecule. Solvent molecules were omitted.