Steroid derivatives. XXVIII. Preparation of 1-methyl-5α-androstane derivatives

1964 ◽  
Vol 29 (12) ◽  
pp. 3089-3095 ◽  
Author(s):  
B. Pelc
Keyword(s):  
Androstane Derivatives

STEROIDSTRUKTUR UND LEBERTOXIZITÄT

1967 ◽  
Vol 54 (1) ◽  
pp. 73-84 ◽  
Author(s):  
H. L. Krüskemper ◽  
G. Noell
Keyword(s):  
Alkaline Phosphatase ◽  
Liver Function ◽  
Blood Coagulation ◽  
Electrophoretic Pattern ◽  
Coagulation Factors ◽  
Blood Coagulation Factors ◽  
Methyl Group ◽  
Liver Functions ◽  
Male Subjects ◽  
Androstane Derivatives

ABSTRACT In male subjects investigations have been carried out regarding the effect of C1- and C17-methylated androstane derivatives (20 mg per day, orally, two weeks) on liver functions (parameters: activities of GPT, GOT, alkaline phosphatase and cholinesterase in serum; electrophoretic pattern; blood coagulation factors V, VII, X and prothrombin; BSP-retention). In addition to the well known hepatotropic action of 17α-alkylated C-19-steroids a quasi-axial 1α-methyl configuration (in 1α-methylandrost-2-en-17β-ol) definitely increased BSP-retention and several coagulation factors. These steroid effects decreased gradually when a methyl group was introduced in C1 equatorially (1-methylandrost-1-en-17β-ol-3-one) or quasi-equatorially (1β-methylandrost-2-en-17β-ol), the latter compound completely lacking from any influence on parameters of liver function under investigation.

Synthesis of 11-hydroxylated androstane derivatives

1980 ◽  
Vol 45 (6) ◽  
pp. 1845-1849 ◽  
Author(s):  
Jan Fajkoš ◽  
Jiří Joska
Keyword(s):  
Selective Reduction ◽  
Reaction Conditions ◽  
Androstane Derivatives

Reaction conditions for selective reduction of 3- and 17-oxo groups are described and applied to syntheses of 11-hydroxylated derivatives.

Synthesis, structural analysis and antitumor activity of novel 17α-picolyl and 17(E)-picolinylidene A-modified androstane derivatives

2015 ◽  
Vol 23 (7) ◽  
pp. 1557-1568 ◽  
Author(s):  
Jovana J. Ajduković ◽  
Katarina M. Penov Gaši ◽  
Dimitar S. Jakimov ◽  
Olivera R. Klisurić ◽  
Suzana S. Jovanović-Šanta ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Antitumor Activity ◽  
Androstane Derivatives

Testosterone Metabolism in Streptomyces hydrogenans

1975 ◽  
Vol 30 (3-4) ◽  
pp. 266-270 ◽  
Author(s):  
Claus Markert ◽  
Brigitte Betz ◽  
Lothar Träger
Keyword(s):  
Cell Wall ◽  
Thin Layer ◽  
Membrane Fraction ◽  
Culture Medium ◽  
Specific Radioactivity ◽  
Two Dimensional ◽  
Specific Staining ◽  
Testosterone Metabolism ◽  
Layer Chromatography ◽  
Androstane Derivatives

Abstract Testosterone, Androst-4-en-3,17-dione, Enzyme Induction, S trep to m yces hydrogenans After cultivation of S trep to m yces hydrogenan s in the presence of 3H-labelled testosterone, radio­ active steroids were extracted separately from the cytosolic, ribosomal and cell wall-membrane fraction of the cells and from the culture medium, respectively.. The separation of the steroids was performed by one-and two-dimensional thin layer chromatography (TLC). The identification of the main metabolites was achieved by crystallization to constant specific radioactivity, specific staining procedures and acetylation. The oxidation of testosterone to androst-4-en-3,17-dione is by far the predominating reaction, which is almost finished after 3 h cultivation. Androst-4-en-3,17-dione is mainly transferred into the culture medium and partly accumulated within the cell wall-membrane fraction. High polar steroid metabolites and androstane derivatives are present in very small amounts only.

scholarly journals Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies

Antibiotics ◽  
2020 ◽  
Vol 9 (5) ◽  
pp. 224 ◽  
Author(s):  
Lela Amiranashvili ◽  
Nanuli Nadaraia ◽  
Maia Merlani ◽  
Charalampos Kamoutsis ◽  
Anthi Petrou ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
In Silico ◽  
Web Applications ◽  
Experimental Studies ◽  
Docking Studies ◽  
Minimum Fungicidal Concentration ◽  
Antibacterial And Antifungal ◽  
Mic Minimum Inhibitory Concentration ◽  
Androstane Derivatives

We evaluated the antimicrobial activity of thirty-one nitrogen-containing 5-α-androstane derivatives in silico using computer program PASS (Prediction of Activity Spectra for Substances) and freely available PASS-based web applications (such as Way2Drug). Antibacterial activity was predicted for 27 out of 31 molecules; antifungal activity was predicted for 25 out of 31 compounds. The results of experiments, which we conducted to study the antimicrobial activity, are in agreement with the predictions. All compounds were found to be active with MIC (Minimum Inhibitory Concentration) and MBC (Minimum Bactericidal Concentration) values in the range of 0.0005–0.6 mg/mL. The activity of all studied 5-α-androstane derivatives exceeded or was equal to those of Streptomycin and, except for the 3β-hydroxy-17α-aza-d-homo-5α-androstane-17-one, all molecules were more active than Ampicillin. Activity against the resistant strains of E. coli, P. aeruginosa, and methicillin-resistant Staphylococcus aureus was also shown in experiments. Antifungal activity was determined with MIC and MFC (Minimum Fungicidal Concentration) values varying from 0.007 to 0.6 mg/mL. Most of the compounds were found to be more potent than the reference drugs Bifonazole and Ketoconazole. According to the results of docking studies, the putative targets for antibacterial and antifungal activity are UDP-N-acetylenolpyruvoylglucosamine reductase and 14-α-demethylase, respectively. In silico assessments of the acute rodent toxicity and cytotoxicity obtained using GUSAR (General Unrestricted Structure-Activity Relationships) and CLC-Pred (Cell Line Cytotoxicity Predictor) web-services were low for the majority of compounds under study, which contributes to the chances for those compounds to advance in the development.

scholarly journals Synthesis of Androstane Derivatives with a Heteroatom

2016 ◽  
Vol 28 (12) ◽  
pp. 2635-2640 ◽  
Author(s):  
Isidora Nogo ◽  
Maja Sremacki ◽  
Evgenija Ðurendic
Keyword(s):  
Androstane Derivatives

scholarly journals Purification and properties of a new testosterone 17β-dehydrogenase (NADP+) from guinea-pig liver

1977 ◽  
Vol 163 (3) ◽  
pp. 401-407 ◽  
Author(s):  
E Kaguera ◽  
S Toki
Keyword(s):  
Guinea Pig ◽  
Column Chromatography ◽  
Gel Filtration ◽  
Deae Cellulose ◽  
Supernatant Fraction ◽  
Pig Liver ◽  
Ring Junction ◽  
Purification And Properties ◽  
Androstane Derivatives ◽  
Guinea Pig Liver

As a result of studies of guinea-pig live testosterone 17beta-dehydrogenase (NADP+) (EC 1.1.1.64), a new testosterone 17beta-dehydrogenase was discovered. The new enzyme was purified to a single homogeneous protein from the 105 000 g-supernatant fraction of guinea-pig liver by (NH4)2SO4 fractional precipitation and two gel-filtration stages, DEAE-cellulose column chromatography and hydroxyapatite column chromatography. It was characterized by many properties. The enzyme has almost the same properties as the classical testosterone 17beta-dehydrogenase (NADP+) (EC 1.1.1.64), with respect to cofactor requirement, pH optima for dehydrogenation, effect of phosphate ion on the NAD+-dependent reaction and molecular weight, but characteristic differences were observed in substrate-specificity between the two dehydrogenases. With various androstane derivatives, the configuration of the A/B-ring junction was closely connected with enzyme activity. 5alpha-Androstanes, such as 5alpha-androstane-3alpha,17beta-diol, 5alpha-androstane-3beta,17beta-diol and 17beta-hydroxy-5alpha-androstan-3-one, and 5beta-congeners, such as 5beta-androstane-3alpha,17beta-diol, 5beta-androstane-3beta,17beta-diol and 17beta-hydroxy-5beta-androstan-3-one, served as substrates for both the EC 1.1.1.64 enzyme and the new enzyme. The EC 1.1.1.64 enzyme oxidized testosterone more rapidly than did the new enzyme. These comparisons were based on the relative activities, apparent Km values and apparent Vmax values.

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