A Computational Study of Euglobal G1 – An Acylphloroglucinol with Anticancer Activity

Euglobal G1 (E-G1) is an acylphloroglucinol exhibiting anticancer activity. The phloroglucinol moiety is a derivative of jensenone and forms a chroman skeleton fused to a terpene unit. A computational study of E-G1 was carried out in vacuo at the HF/6-31G(d,p), DFT/B3LYP/6-31+G(d,p) and MP2/HF/6-31G(d,p) levels, and in solution at the DFT/B3LYP/6-31+G(d,p) level, with the PCM model and considering three solvents – chloroform, acetonitrile and water. All the computed molecular properties are reported and analysed in detail. The results in vacuo are compared with those of two other molecular structures, one (E-G2) differing by interchanged positions of the acyl chains with respect to E-G1 and proven non-active against cancer; the other (GX) differing from E-G1 only by the position of the bridge in the terpene unit. It appears reasonable to infer that the nature and positions of the two acyl chains in E-G1 have a role in determining its biological activity.