Synthesis and Cytotoxic Studies of Hydroximino Derivatives of Some 16E-Arylidenosteroids

Chattopadhaya, Raja; Jindal, D. P.; Minu, Maninder; Gupta, Ranju

doi:10.1055/s-0031-1297011

Cited by 8 publications

(13 citation statements)

References 9 publications

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“…Benzylidene derivatives obtained by the Claisen–Schmidt condensation of steroidal ketones may serve as starting materials for the synthesis of compounds of pharmacological importance or may show favourable biological activity themselves . The 16‐arylidene group was found to be a good pharmacophore for cytotoxic activity.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, 16‐arylidene derivatives of androst‐5‐en‐3β‐ol‐17‐one and their 4‐aza‐analogues were reported to prevent the progression of lipopolysaccharide‐induced neuroinflammation and subsequent neurodegeneration, so they represent a new class of neuroprotective agents for the treatment of Alzheimer's and Parkinson's diseases . All arylidene derivatives were obtained from the corresponding steroidal 17‐ketones and aromatic aldehydes in base‐catalysed reactions in the presence of lithium diisopropylamide (LDA), KF/Al 2 O 3 , or alkali‐hydroxides …”

Section: Introductionmentioning

confidence: 99%

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The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

et al. 2018

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Switchable polarity recyclable solvent mixtures were applied as reaction medium and catalyst to replace the conventional base catalysts in the Claisen–Schmidt condensation of 17‐oxo steroids with aromatic aldehydes. Reversibility between ionic and nonionic forms of the new 2‐n‐butyl‐1,1,3,3‐tetramethylguanidine (nBu‐TMG)/ethylene glycol/CO2 and 2‐tert‐butyl‐1,1,3,3‐tetramethylguanidine (tBu‐TMG)/ethylene glycol/CO2 systems were proved by conductivity measurements. The structure of the ionic form was established by 1H NMR and IR measurements and by quantum chemical calculations. The steroidal products with androstane and estrane skeleton were characterised with spectroscopic methods (NMR, IR, MS).

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

et al. 2018

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“…On the other hand, A-ring arylideneandrostane derivatives were also described but much less frequently [ 31 , 54 , 55 ]. In addition to cytotoxic effects, several studies reported other biological activities, such as aromatase inhibition, anti-inflammatory, neuroprotective and skeletal muscle relaxing activities and tissue-selective androgen receptor modulator effects [ 38 , 57 , 58 ]. A selection of the most relevant 16 E -arylideneandrostane derivatives is presented in Table 1 .…”

Section: Bioactivity Of 2- and 16 E -Arylideneamentioning

confidence: 99%

Highlights on Steroidal Arylidene Derivatives as a Source of Pharmacologically Active Compounds: A Review

et al. 2021

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Steroids constitute a unique class of chemical compounds, playing an important role in physiopathological processes, and have high pharmacological interest. Additionally, steroids have been associated with a relatively low toxicity and high bioavailability. Nowadays, multiple steroidal derivatives are clinically available for the treatment of numerous diseases. Moreover, different structural modifications on their skeleton have been explored, aiming to develop compounds with new and improved pharmacological properties. Thus, steroidal arylidene derivatives emerged as a relevant example of these modifications. This family of compounds has been mainly described as 17β-hydroxysteroid dehydrogenase type 1 and aromatase inhibitors, as well as neuroprotective and anticancer agents. Besides, due to their straightforward preparation and intrinsic chemical reactivity, steroidal arylidene derivatives are important synthetic intermediates for the preparation of other compounds, particularly bearing heterocyclic systems. In fact, starting from arylidenesteroids, it was possible to develop bioactive steroidal pyrazolines, pyrazoles, pyrimidines, pyridines, spiro-pyrrolidines, amongst others. Most of these products have also been studied as anti-inflammatory and anticancer agents, as well as 5α-reductase and aromatase inhibitors. This work aims to provide a comprehensive overview of steroidal arylidene derivatives described in the literature, highlighting their bioactivities and importance as synthetic intermediates for other pharmacologically active compounds.

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“…In this regard, different derivatives of androsterone (3α-hydroxy-5α-androstan-17-one) have been excessively studied as potent anti-cancer agents (Figure 1) [18,19]. Recently, the significant cytotoxic and aromatase inhibitory potential of a large number of androsterone derivatives containing substitution at position 16 have been reported [12,20,21]. Bansal et.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone

et al. 2013

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Background and the purpose of the studyModified androsterone derivatives are class of steroidal compounds with potential anticancer properties. Various steroidal derivatives containing substitution at position 16 have shown diversified pharmacological activities. In the present study, a new series of cytotoxic 16-(substituted benzylidene) derivatives of dehydroepiandrosterone (DHEA) were synthesized and evaluated against three different cancer cell lines.MethodsThe cytotoxic 16-(substituted benzylidene) derivatives of DHEA were synthesized via aldol condensation of DHEA with corresponding benzaldehyde derivatives. The cytotoxic activity of synthesized derivatives was evaluated against three different cancer cells including KB, T47D and SK-N-MC cell lines by MTT reduction colorimetric assay.ResultsThe results indicated that 16-(substituted benzylidene) derivatives of DHEA could be served as a potent anti-cancer agent. The 3-cholro benzylidene derivatives of DHEA was the most potent synthesized derivative especially against KB and T47D cell lines (IC50 values were 0.6 and 1.7 μM; respectively).ConclusionThe cytotoxic potential of novel benzylidene derivatives of DHEA is mainly attributed to the position and nature of the substituted group on the benzylidene pendant.

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Synthesis and Cytotoxic Studies of Hydroximino Derivatives of Some 16E-Arylidenosteroids

Cited by 8 publications

References 9 publications

The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

The Use of Switchable Polarity Solvents for the Synthesis of 16‐Arylidene Steroids via Claisen–Schmidt Condensation

Highlights on Steroidal Arylidene Derivatives as a Source of Pharmacologically Active Compounds: A Review

Synthesis and In vitro cytotoxic activity evaluation of (E)-16-(substituted benzylidene) derivatives of dehydroepiandrosterone

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