1056-93-5Relevant articles and documents
Synthesis and characterization of steroidal heterocyclic compounds, DNA condensation and molecular docking studies and their in vitro anticancer and acetylcholinesterase inhibition activities
Ali, Abad,Asif, Mohd,Khanam, Hena,Mashrai, Ashraf,Sherwani, Mohd Asif,Owais, Mohammad,Shamsuzzaman
, p. 75964 - 75984 (2015)
A facile, convenient and efficient approach for the synthesis of a new series of steroidal heterocyclic compounds (4-12) by reacting a mixture of compounds (1e-3e) with o-aminothiophenol/o-aminophenol/o-phenylenediamine is reported. The structural assignment of products is confirmed on the basis of IR, 1H NMR, 13C NMR, MS and analytical data. The compounds obey the Lipinski's 'Rule of Five' analysis based on computational prediction and pharmacokinetic properties. The anticancer activity has been tested in vitro against three cancer cell lines Hep3B (human hepatocellular carcinoma), MCF7 (human breast adenocarcinoma), HeLa (human cervical carcinoma) and one non-cancer normal cell i.e. PBMCs (peripheral blood mononuclear cell) by MTT assay. In addition, the synthesized compounds are also tested for their in vitro antioxidant activity by various reported methods in which compounds 10-12 exhibited good antioxidant activity. Nonenzymatic degradation of DNA has been investigated. The acetylcholinesterase (AChE) inhibitor activities of the steroidal derivatives are also evaluated using Ellman's method. Moreover, the application of compound 6 as a DNA gene transporter is evaluated by DNA condensation and ascertained by employing TEM and AFM, which illustrate that the compound 6 induces the condensation of CT-DNA. Molecular docking studies further characterize the interaction of the synthesized compounds with DNA. 2015
-
Mauthner,Suida
, p. 648,652 (1903)
-
SnCl2·2H2O-Mg-H2O: A Mild Reagent System for the Regioselective Transformation of Conjugated Nitroalkenes to Carbonyl Compounds
Das, Nalin B.,Sarangi, Chintamani,Nanda, Bhagabat,Nayak, Amalendu,Sharma, Ram P.
, p. 28 - 29 (2007/10/03)
Nitroalkenes and 6-nitro-Δ5-steroids have been converted regioselectively and in good yields into carbonyl compounds and 6-oxo steroids, respectively, by the SnCl2·2H2O-Mg-H2O system in tetrahydrofuran.
Oxidation of steroidal compounds with Mn(III) acetate
Ahmad,Ahamad,Ansari,Kardash
, p. 430 - 434 (2007/10/02)
Mn(III) acetate oxidation of cholest-5-ene (I) in acetic acid-acetic anhydride affords 5 ξ-hydroxycholestan-6 ξ-yl acetic acid γ-lactone (VI), 5 ξ-acetoxycholestan-6 β-ol (VII) and 6 ξ-carboxymethylenecholest-4-ene (VIII). Under similar reaction conditions 3 β-acetoxycholest-5-ene (II) gives 4 β-hydroxycholest-5-en-3β-yl acetic acid γ-lactone (IX), its 7 α-acetoxy analogue (X) and 3 β-acetoxy-5 β-hydroxycholestane-6 ξ-yl acetic acid γ-lactone (XI). The chloroolefin (III) gives X and 3 β-chloro-5 α-cholestan-6 β-ol (XII). I with Mn (III) acetate in propionic acid-propionic anhydride affords 2'-methyl-5ξ-hydroxycholestan-6ξ-yl acetic acid γ-lactone (XIII) and 2'-methyl-7α-propionoxy-4 β-hydroxycholest-5-en-3β-yl acetic acid γ-lactone (XIV). II and III give 3β-propionoxycholest-5-ene (XV), the product of nucleophilic substitution at C-3. The difference noticed in the behavior of Mn (III) acetate in acetic acid-acetic anhydride and Mn (III) acetate in propionic acid-propionic anhydride towards II and III eludes rationalization. 7-Oxocholest-5-en-3β-yl acetate (IV) when treated with Mn (III) acetate in acetic acid-acetic anhydride gives 7-oxocholesta-3,5-diene (XVI), 7-oxocholest-5-en-3β, 4α-yl diacetate (XVII) and 4β-hydroxy-7-oxocholest-5-en-3β-yl acetic acid γ-lactone (XVIII). Under similar conditions 3-oxocholest-4-ene (V) affords 3-oxocholest-4-en-6 α-yl acetate (XIX), its 6β-epimer (XX) and 3-oxocholesta-1, 4-diene (XXI). The products have been characterized on the basis of elemental analysis, spectral values and in some cases by conversions and comparison with authentic samples.
