A facile synthesis and theoretical analysis of a steroid-cyclophano

The synthesis of steroid-benzenacyclononaphanone was performed using some chemical tools. In the first stage, an indol-pregnenolone derivative (3) was prepared by the reaction of pregnenolone with phenyl-hydrazine. Additionally, the compound 3 was bound to ethylenediamine to form a new indol-pregnenolone derivative (4). The third stage was achieved by synthesis of a benzamide derivative (6) by the reaction of 4 with 3,5-dinitrobenzoic acid using boric acid as catalyst. Finally, an ether group involved in the steroid-benzenacyclononaphanone derivative (7) was developed using the compound 6 in presence of dimetyhyl sulfoxide at mild conditions. The chemical structure of steroid derivatives was confirmed by NMR spectroscopic data. On the other hand, some physicochemical parameters of compounds 3, 4, 6 and 7 (logP, π, R_m, V_m P_a l_r and S_t) were analyzed. The results showed that value of logP was greater for 7 as compared to compounds 3, 4 and 6; this phenomenon is translated at a higher of lipophilicity degree. Additionally, the values of R_mand V_m were higher for compound 7 which may have higher steric impediment in some biological systems in comparison with compounds 3, 4 and 6. Furthermore, the values of R_m and V_m were higher for compound 7 which could result in some steric hindrance in greater biological systems as compared to compounds 3, 4 and 6.