Facile Synthesis of Two Benzamidine-Steroid Derivatives
Figueroa-Valverde Lauro, Díaz-Cedillo Francisco, García-Cervera Elodia, Pool-Gómez Eduardo, López-Ramos Maria, Rosas-Nexticapa Marcela, Hau-Heredia Lenin and Sarabia-Alcocer BetyAffiliation:
Laboratory of Pharmaco-Chemistry, Faculty of Chemical Biological Sciences, University Autonomous of Campeche, Av. AgustínMelgar s/n, Col Buenavista C.P.24039 Campeche Cam., México.
AbstractSeveral steroid derivatives have been synthesized; however, the nevertheless, 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 involve 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 presence of dimetyhylsulfoxide. The compound 5 was made reacting 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 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 made reacting 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 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 simple procedure, low cost, and ease of workup.
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