A study of the antiviral activity of several new hydrazones and amines and amides of 5D-steroids that were synthesized by us earlier found highly and moderately active compounds. The structures of the synthesized compounds were proven using IR, PMR, 13 C NMR, and mass spectral data.Broad spectra of biological activity make steroids and their derivatives promising for discovering new efficacious drugs [1][2][3]. The high antibacterial, antiviral, and antitumor activity of hydrazono-, amino-, and amido-derivatives of the androstane, estrane, and cholestane series [4][5][6][7][8] and the expanded scope of their synthetic analogs helped to find new biological properties of these compounds.In continuation of research on the synthesis of bioactive 5D-steroids from epiandrosterone 1 [9, 10], a transformation product of tigogenin, hydrazones 2-4 were obtained.
New peptide derivatives of 17E-amino-5D-androstan-3E-ol were synthesized. Their structures were elucidated using PMR and 13 C NMR spectra and elemental analyses.Modification of steroids with pharmacophores in order to discover new highly active compounds is a critical problem [1][2][3][4]. Saturated and unsaturated 17E-aminosteroids are used as intermediates to synthesize biologically active derivatives [5,6]. Peptide analogs of amidosteroids, among which compounds with various physiological activities such as anti-arrhythmic and antitumor have been found, were prepared by adding amino acids to aminosteroids [7,8].Previously, we studied the possibility of producing peptide derivatives of 5D-steroidal oximes, intermediates in the transformation of tigogenin. New peptide analogs were prepared using the known method [9, 10] for synthesizing reagents, i.e., N-protected (D-aminoacyl)benzotriazoles, and O-acylation of 17-hydroximino-5D-androstanolone and 20-hydroximines of 3E-acetoxy-and 3E-hydroxy-5D-pregn-16-enolone [11].The goal of the present work was to study N-acylation of 17E-amino-5D-androstan-3E-ol (1) in order to synthesize biologically active amino derivatives. A similar modification of Amefalone (3D-amino-2E-hydroxy-5D-androstan-17-one), which possesses high anti-arrhythmic activity, decreased its toxicity [12]. Peptide derivatives 2-5 were synthesized after the optimum acylation conditions were developed. The reaction was carried out by refluxing mixtures of 1 and the corresponding reagents (N-Cbz-L-Ala-Bt; N-Cbz-L- Val-Bt, N-Cbz-L-Phe-Bt, and N-Cbz-L-Ala-L-Val-Bt) in anhydrous THF in the presence of TEA. Starting amine 1, which exhibited anti-arrhythmic activity [13], was prepared from tigogenin using the method developed by us [14].The structures of synthesized 2-5 were confirmed by PMR and 13 C NMR spectral data and elemental analyses. PMR spectra of 2-5 showed resonances for angular 18-CH 3 and 19-CH 3 as singlets at G 0.66-0.88 ppm. Multiplets for the 3D protons appeared at G 3.58 ppm; 17D-protons, G 3.77-3.90 ppm. Methyl resonances of the amino acids of 2 and 5 (alanine groups) appeared as doublets at G 1.37 ppm; of 3 (valine group), as a multiplet at G 0.95 ppm; of dipeptide 5 (valine
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