A Facile Synthesis and Theoretical Analysis of a Steroid-Cyclophano

Author(s): Figueroa-Valverde Lauro , Díaz-Cedillo Francisco , Rosas-Nexticapa Marcela , García-Cervera Elodia , Pool-Gómez Eduardo , Camacho-Luis Abelardo , López-Ramos María , García-Martínez Rolando .

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 9 , 2015

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Graphical Abstract:


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, π,Rm,Vm P0 I r and St) 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 Rmand Vm were heigher for compound 7 which may have heigher steric impediment in some biological systems in comparison with compounds 3, 4 and 6.

Furthermore, the values of Rm and Vm were higher for compound 7 which could result in some steric hindrance in greater biological systems as compared to compounds 3, 4 and 6.

Keywords: Benzenacyclononaphanone, boric acid, carbamazepine, steroid, synthesis, thiourea.

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Article Details

Year: 2015
Page: [614 - 621]
Pages: 8
DOI: 10.2174/157017861209151006165315
Price: $58

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