New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities

Krstić, Natalija M.; Bjelaković, Mira S.; Pavlović, Vera P.; Robeyns, Koen; Juranić, Zorica D.; Matić, Ivana Z.; Novaković, Irena; Sladić, Dušan

doi:10.1016/j.steroids.2012.01.021

Cited by 30 publications

(19 citation statements)

References 37 publications

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“…Survival of the target cells was determined by an MTT test aer 72 h of continuous activity of the agents, according to the method of Mosmann, 67 which was modied by Ohno and Abe 68 and used in our previous studies. [37][38][39] Cisplatin was used as a positive control.…”

Section: Biologymentioning

confidence: 99%

“…Then, 200 mL complete nutrient medium (Dulbecco's modied Eagle's medium with high glucose and 4 mM L-glutamine supplemented with 10% heat-inactivated FBS and 25 mM HEPES) was added to the control cell sample, while solutions in nutrient medium of the tested compounds were added to the other cell samples. The plates were incubated for 20 h at 37 of EA.hy926 cells were captured using an inverted phasecontrast microscope aer treatment for 20 h. In our experiment, the EA.hy926 cells were exposed to low sub-toxic concentrations of the investigated compounds (concentrations of IC 20 obtained by an MTT test aer treatment that lasted for 24 h): for compound 2a, the applied concentration was 3.5 mM, for compounds 2b, 2c and 2e the concentration was 10 mM, for compound 5a the concentration was 4.5 mM and for compound 5d the concentration was 60 mM.…”

Section: Live Subject Statementmentioning

confidence: 99%

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Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines

et al. 2016

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Section: Biologymentioning

confidence: 99%

Section: Live Subject Statementmentioning

confidence: 99%

Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines

et al. 2016

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“…We examined steroids, one of the largest and most diverse class of natural products . Heterosteroids bearing annulated azaheterocycles are known to exhibit a wide range of biological activities, e.g., antiproliferative, anti‐inflammatory, and antimicrobial . We first examined estrone 7 and 3β‐hydroxyandrost‐5‐en‐17‐one 9 under standard conditions (Scheme , lines a,b).…”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of 4‐ and 5‐Substituted 2‐Aminopyrimidines by Coupling of β‐Chlorovinyl Aldehydes and Guanidines

et al. 2017

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A general, practical, and simple synthesis of functionalized 2‐aminopyrimidines starting from β‐chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two‐step sequence involving the Vilsmeier–Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional‐group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

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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].…”

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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New androst-4-en-17-spiro-1,3,2-oxathiaphospholanes. Synthesis, assignment of absolute configuration and in vitro cytotoxic and antimicrobial activities

Cited by 30 publications

References 37 publications

Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines

Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines

Efficient Synthesis of 4‐ and 5‐Substituted 2‐Aminopyrimidines by Coupling of β‐Chlorovinyl Aldehydes and Guanidines

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

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