- Synthesis and characterization of steroidal heterocyclic compounds, DNA condensation and molecular docking studies and their in vitro anticancer and acetylcholinesterase inhibition activities
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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
- Ali, Abad,Asif, Mohd,Khanam, Hena,Mashrai, Ashraf,Sherwani, Mohd Asif,Owais, Mohammad,Shamsuzzaman
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- Microwave-assisted transformation of α,β- and β,γ-unsaturated nitroalkenes into carbonyl compounds
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Vinyl and allylic nitroalkenes have been converted into the corresponding carbonyl compounds in good yield using tin(II) chloride dihydrate under microwave irradiation.
- Das, Deba D.,Nayak, Amalendu,Nanda, Bhagabat,Das, Nalin B.
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p. 481 - 482
(2007/10/03)
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- SnCl2·2H2O-Mg-H2O: A Mild Reagent System for the Regioselective Transformation of Conjugated Nitroalkenes to Carbonyl Compounds
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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.
- Das, Nalin B.,Sarangi, Chintamani,Nanda, Bhagabat,Nayak, Amalendu,Sharma, Ram P.
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- Oxymercuration-demercuration of steroidal olefins: Extension and reinvestigation
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Cholesterol (I) on mercuration-demercuration gives 3β-acetoxycholest-5-ene (II), 3β,6β-dihydroxy-5α-cholestane (V), 6β-acetoxy-3β-hydroxycholest-4-ene (VI), 3β,6β-dihydroxycholest-4-ene (VII) and its diacetate (VIII).Under similar reaction conditions, II affords I, VIII, 3β6β-diacetoxy-5α-cholestane (X) and 5ξ-acetoxycholestan-3-one (XI).On demercuration with NaBH4 - NaOH, the adduct from I gives II, V, VII and cholest-4-en-3-one (IX).Under similar conditions, the adduct from II affords I, V, VII and XI.OM - DM of cholest-5-ene (III) and 3β-chlorocholest-5-ene (IV) has been reinvestigated in order to suport our earlier observation in the sense that 3-substituted products are obtained from III.Cholest-5-ene (III) on OM - DM gives I and II, in addition to the products reported earlier.On demercuration with NaBH4-ethylene glycol the adduct from III gives additional products, such as 4β-acetoxycholest-5-en-7-one (XII) and 7-acetoxy-3β-hydroxycholest-4-en-6-one (XIII).The chloroolefin (IV) on OM - DM gives an additional product, 3β-chloro-6β-hydroxy-5α-cholestane (XIV).Interestingly the mercury adduct from IV on demercuration with NaBH4-ethylene glycol affords an additional product, 3β-(2-acetoxyethoxy)cholest-5-ene (XV).The structures of the compounds have been established by elemental analyses, spectral data, chemical transformation and comparison with authentic samples.Mechanisms for the formation of V and VIII from I and that of II and XII from III have been proposed.
- Ahmad, M. S.,Ayad, Tariq M.
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p. 763 - 768
(2007/10/02)
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- Oxidation of steroidal compounds with Mn(III) acetate
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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.
- Ahmad,Ahamad,Ansari,Kardash
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p. 430 - 434
(2007/10/02)
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- REACTION OF 5,6α-EPOXY-5α-CHOLESTANE AND 5,6α-EPOXY-5α-STIGMASTANE WITH BF3:ETHERATE
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Reaction of 3β-chloro-5,6α-epoxy-5α-cholestane (1) with BF3:etherate afforded 3β-chloro-5α-cholestan-6-one (3), 3β-chloro-5β,14β-dimethyl-18,19-bisnor-10α-cholest-13(17)-en-6α-ol (4), 3β-chloro-5β-methyl-19-nor-cholest-9(10)-en-6α-ol (5) and 3β-chloro-6β-fluoro-5α-cholestan-5α-ol (6).On similar treatment 3β-acetoxy-5,6α-epoxy-5α-stigmastane (2) gave 3β-acetoxy-5α-stigmastan-6-one (7), 3β-acetoxy-5β,14β-dimethyl-18,19-bisnor-10α-stigmast-13(17)-en-6α-ol (8), 3β-acetoxy-5β-methyl-19-nor-stigmast-9(10)-en-6α-ol (9) and 3β-acetoxy-6β-fluoro-5α-stigmast-5α-ol (10).Compounds 4 and 8 and 5 and 9 were formed via "backbone" and Westphalen rearrangements.The structures of these compounds were established on the basis of spectral data and by comparison with authentic samples.
- Shafiullah,Jamaluddin, Malik
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- Reduction of 3β-chloro-6-nitrocholest-5-ene with Raney nickel - hydrazine hydrate: A synthesis of dimers
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Treatment of 3β-chloro-6-nitrocholest-5-ene (I) with Raney nickel - hydrazine hydrate affords 3β,3β-dichloro-5α,5'α-6,6'-bis-azocholestane (III) and 3α,5α:3'α,5'α-dicyclo-6,6'-bis-azocholestane (IV) along with 3β-chlorocholestan-6-one (II).
- Shafiullah,Husain, Shakir,Basha, D. M.,Ansari, M. R.
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p. 683 - 684
(2007/10/02)
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- Recation of Nitro-alkenes with Iodotrimethylsilane: A New Method for the Conversion of Vinyl Nitrosteroids to Ketosteroids
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Iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide effects the reduction of nitro-alkenes (1a-e) and (5) at -5 to O deg C to furnish the ketones (2a-e) and (6) respectively as the major products.
- Singhal, Gireesh M.,Das, Nalin B.,Sharma, Ram P.
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p. 1470 - 1471
(2007/10/02)
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- Reduction of Steroidal Nitroolefins with Zinc-Acetic Acid without Added Water
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Zinc-acetic acid reduction (without added water) of steroidal nitroolefins (I-III) leads to the formation of respective N-acetylated enamines (X-XII) alongwith the parent ketones (IV-VI) and the oximes (VII-IX).These products have been identified on the basis of their spectral properties and by comparison with authentic samples where available.
- Ahmad, M. S.,Raza, S. K.
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p. 579 - 580
(2007/10/02)
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- Reaction of Nitrosyl Chloride Gas with Unsaturated Steroids
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Reaction of nitrosyl chloride gas at 0 deg C with 3,5-cholestadiene (1) provided 3,6β-dinitro-5-chloro-5α-cholest-3-ene (4) and with 3α,5-cyclo-5α-cholestan-6-one (2) afforded 3β-chloro-5-nitro-5α-cholestan-6-one (7) and 3β-chloro-6-nitrato-5-cholestene (8).Similar reaction with 6-hydroxylimino 3α,5-cyclo-5α-cholestane (3) gave 3β,6-dichloro-6-cholestene (10), 3β-chloro-6-nitratoimino-5α-cholestane (11) and 3β,5-dichloro-6-nitroimino-5β-cholestane (12).Compound 12 upon hydrolysis furnished 3β,5-dichloro-5β-cholestan-6-one (14).The structures of these compounds were established on the basis of their spectral properties, and some pertinent chemical transformations.Mechanisms for the formation of some unusual products are discussed.
- Shafiullah,Rafiuddin, Ansari M.,Husain, Shakir
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p. 3411 - 3414
(2007/10/02)
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- N-Nitrosation of Some Steroidal 6-Ketoximes
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Steroidal 6-nitrimines, namely 6-nitrimino-5α-cholestane (IV) and its 3β-acetoxy (V) and 3β-chloro (VI) analogues have been obtained by the N-nitrosation of the respective oximes (I-III).The nitrimines (IV-VI) on alkali isomerization give N-nitroenamines (X-XII).NaBH4 reduction of IV-VI affords the respective nitroamines (XIII-XV).The products have been characterized on the basis of their spectral and analytical data and chemical transformations.
- Ahmad, M. S.,Raza, S. K.
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p. 774 - 775
(2007/10/02)
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- A Novel Method for Preparation of Steroidal Ketoximes from Nitroolefins
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Steroidal 6-nitroolefins (I-IV) undergo facile reaction with NH3-MeOH-Zn yielding exclusively the corresponding 6-one oximes (V-VIII) in quantitative yields.The method appears to be of general applicability.
- Habib, Rubina,Husain, Mubarak,Husain, Mashkoor,Khan, Naseem H.
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- Allylic Bromination of Nitrosteroids
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Bromination of 3β-acetoxy-6-nitrocholest-5-ene (I), 3β-chloro-6-nitrocholest-5-ene (II) and 6-nitrocholest-5-ene (III) afford 3β-acetoxy-7α-bromo-6-nitrocholest-5-ene (IV), 3β-chloro-7α-bromo-6-nitrocholest-5-ene (V) and 4β,7α-dibromo-6-nitrocholest-5-ene (VI) respectively.IV and V on debromination furnish 3β-acetoxy-6-nitrocholesta-4,6-diene (VII) and 6-nitrocholesta-2,4,6-triene (VIII) respectively.VII and VIII on refluxing with Zn - AcOH afford the ketones (IX) and (X) respectively.IV, V and VI on treatment with Zn - AcOH at room temperature give the ketones (XI), (XII) and (XIII) respectively.All the ketones (IX - XIII) are known in literature.
- Shafiullah,Husain, Shakir,Ali, Hasrat,Ogura, H.,Takayanagi, H.
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