Letters in Organic Chemistry

Gwilherm Evano
Free University of Brussels


Facile Synthesis of Two Benzamidine-steroid Derivatives

Author(s): Figueroa-Valverde Lauro, Diaz-Cedillo Francisco, García-Cervera Elodia, Pool-Gómez Eduardo, López-Ramos Maria, Rosas-Nexticapa Marcela, Hau-Heredia Lenin, Sarabia-Alcocer Bety.

Graphical Abstract:


Several steroid derivatives have been synthesized; however, expensive reagents and special conditions are required. Therefore, in this study two benzamidine-steroid derivative were synthetized using several strategies; the first step was achieved by the synthesis of N-(3-Butyl-1-cyclohexyl-4-cyclohexylimino-azetidin-2-ylidene)-4-nitro-benzamide (4) by the reaction of 4-nitrobenzoyl azide, 1-hexyne and N,N’-Dicyclohexylcarbodiimide using cuprous iodide as catalyst. The second involves the preparation of N-(3-Butyl-1-cyclohexyl-4-ciclohexylimino-azetidin-2-ylidene)-4-(naphta len-2- yloxy)-benzamide (5) by the reaction of 4 with β-naphtol in the presence of dimetyhylsulfoxide. The compound 5 was reacted with ethylenediamine to form N-(2-Amino-ethyl)-N´-(butyl-1-cyclohexyl-4-cyclohexylimino-azetidin-2-ylidene)-4- (naph talen-2-yloxy)-benzamide (6) in the presence of boric acid. The following stage was achieved by synthesis of N-(3- Butyl-1-cyclohexyl-4-cyclohexylimino-azetidin-2-ylidene)-N´-[2-(17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14, 15,16,17-tetradecahydro-cyclopenta[a] phenanthren-3-ylideneamino)-ethyl]-4-(naphtalen-2-yloxy)-benzamidine (7) using boric acid as catalyst. Also 6 was reacted with estrone to form N-(3-Butyl-1-cyclohexyl-4-cyclohexylimino-azetidin-2- ylidene)-N´-[2-(3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15, 16-decahydro-cyclopenta[a]phenanthren-17-ylideneamino)- ethyl]-4-(naphtalen-2-yloxy)-benzamidine (8) in the presence of boric acid. The structure of all compounds obtained was confirmed by spectroscopic and spectrometric methods. In conclusion; the methods used offer some advantages such as simple procedure, low cost, and ease of work.

Keywords: Benzamidine, estrone, steroid, testosterone.

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Article Details

Year: 2014
Page: [725 - 730]
Pages: 6
DOI: 10.2174/1570178611666140813210013
Price: $58