570-46-7Relevant articles and documents
Multiple Enone-Directed Reactivity Modes Lead to the Selective Photochemical Fluorination of Polycyclic Terpenoid Derivatives
Pitts, Cody Ross,Bume, Desta Doro,Harry, Stefan Andrew,Siegler, Maxime A.,Lectka, Thomas
supporting information, p. 2208 - 2211 (2017/02/23)
In the realm of aliphatic fluorination, the problem of reactivity has been very successfully addressed in recent years. In contrast, the associated problem of selectivity, that is, directing fluorination to specific sites in complex molecules, remains a great, fundamental challenge. In this report, we show that the enone functional group, upon photoexcitation, provides a solution. Based solely on orientation of the oxygen atom, site-selective photochemical fluorination is achieved on steroids and bioactive polycycles with up to 65 different sp3 C-H bonds. We have also found that γ-, β-, homoallylic, and allylic fluorination are all possible and predictable through the theoretical modes reported herein. Lastly, we present a preliminary mechanistic hypothesis characterized by intramolecular hydrogen atom transfer, radical fluorination, and ultimate restoration of the enone. In all, these results provide a leap forward in the design of selective fluorination of complex substrates that should be relevant to drug discovery, where fluorine plays a prominent role.
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 (2015/09/28)
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
Synthesis of acylated steroidal olefins and their derivatives
Mushfiq,Khan,Shamim, Afreen,Rehman, Rakhshanda
scheme or table, p. 1508 - 1515 (2010/07/15)
Acylation of cholest-5-ene and cholest-5-ene 3-one with anhydrides in the presence of zinc chloride and characterization of products thus obtained on the basis of elemental analysis, spectral data, and chemical transformations are reported. Copyright Tayl
Microwave-assisted transformation of α,β- and β,γ-unsaturated nitroalkenes into carbonyl compounds
Das, Deba D.,Nayak, Amalendu,Nanda, Bhagabat,Das, Nalin B.
, p. 481 - 482 (2007/10/03)
Vinyl and allylic nitroalkenes have been converted into the corresponding carbonyl compounds in good yield using tin(II) chloride dihydrate under microwave irradiation.
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.
Efficient Cleavage of Cyclopropyl Bond by Adjacent Ketyl Radical Generated Under PET Conditions
Pandey, Bipin,Rao, Ashok T.,Dalvi, Pramod V.,Kumar, Pradeep
, p. 3843 - 3848 (2007/10/02)
Photolysis of various conjugated cyclopropyl and epoxy ketones in 20percent triethyl amine (TEA) and ethanol leads to cleavage of cyclopropyl bond.Significant wavelength dependence phenomenon is observed during photolysis for the cleanliness and efficient photo transformation.Steroidal cyclopropyl ketones cleave efficiently at 300nm photolysis, whereas exo-cyclopropyl ketones cleave at 254nm.The regiochemistry of cyclopropyl bond cleavage is governed by the principle of maximum overlap.The nature of chemistry generated by ketyl radical is shown to be a function of methodology of their generation.
Oxymercuration-demercuration of steroidal olefins
Ahmad, M. S.,Raza, S. K.,Kardash, Taufik S.,Ayad, Tariq M.
, p. 855 - 857 (2007/10/02)
Cholest-5-ene (I) on oxymercuration-demercuration affords 5α-cholestan-6β-ol (II) and cholest-4-en-6β-ol (III).Under similar reaction conditions cholest-5-en-3β-yl chloride (IV) gives cholest-5-en-3β-ol (V) and 5α-cholestane-3β,6β-diol (VI).On demercuration with NaBH4-ethylene glycol the mercuriadduct from I gives 6-oxocholest-4-ene (VII), 6-oxocholest-4-en-3β,7α-yl diacetate (VIII), 7-oxocholest-5-en-4α-yl acetate (IX), 6-oxo-cholest-4-en-7α-yl acetate (X) and 7-oxocholest-4-en-3β,6β-diol-3-acetate (XI).Adduct from IV under similar demercuration provides cholest-5-en-3β-yl acetate (XII) and 5α-cholestane-3β,6β-diol diacetate (XIII).Both I and IV failed to provide the expected hydroxy ethers of type XIV in ethylene glycol medium.The identity of these compounds are based on the elemental analyses, spectral data, chemical transformations and comparision with authentic samples where available.
Recation of Nitro-alkenes with Iodotrimethylsilane: A New Method for the Conversion of Vinyl Nitrosteroids to Ketosteroids
Singhal, Gireesh M.,Das, Nalin B.,Sharma, Ram P.
, p. 1470 - 1471 (2007/10/02)
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.
