A Facile Synthesis and Theoretical Analysis of a Steroid-Cyclophano

作者：Lauro Figueroa Valverde^*; Francisco Diaz Cedillo; Marcela Rosas Nexticapa; Elodia Garcia Cervera; Eduardo Pool Gomez; Abelardo Camacho Luis; Maria Lopez Ramos; Rolando Garcia Martinez

来源：Letters in Organic Chemistry, 2015, 12(9): 614-621.

DOI：10.2174/157017861209151006165315

• Benzenacyclononaphanone
• boric acid
• carbamazepine
• steroid
• synthesis
• thiourea

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 phenylhydrazine. 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, pi, R-m, V-m, p(c),I-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-m and 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.

• 出版日期2015