Stereoselective synthesis of selenosteroids

Rodrigues, Oscar E. D.; Souza, Diego de; Soares, Letiére C.; Dornelles, Luciano; Burrow, Robert A.; Appelt, Helmoz R.; Alves, Camila Fillipi dos Santos; Alves, Diego; Braga, Antônio L.

doi:10.1016/j.tetlet.2010.02.090

Cited by 26 publications

(12 citation statements)

References 23 publications

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“…Considering that Rodrigues et al reported that derivatives similar to 2 are characterized by an important prooxidant activity we explored the redox behavior of 2 as well as its GPx-like activity using the 77 Se-NMR and NMR-DTT coupled test [16,17]. Initially, we investigated by 77 Se-NMR spectroscopy, the actual intermediates involved in GPx-like cycle.…”

Section: Resultsmentioning

confidence: 99%

“…Till now, few examples of selenosteroids were reported in the literature and they were tested and proved to be interesting antiproliferative agents following a prooxidant mechanism. Some representative examples are reported in Figure 1 [13,14,15], selenium can be embedded as selenourea, selenocyanate or alkyl/aryl selenide directly introduced in C-3 or C-6 through the S N 2 reaction of a selenolates with a tosylate (VI) or an epoxide (V) affording, in this letter case to a β-hydroxyselenide [16,17].…”

Section: Introductionmentioning

confidence: 99%

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PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Jastrzębska

Mellea

Salerno

et al. 2019

IJMS

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We report here the reaction of in situ prepared PhSeZnCl with steroid derivatives having an epoxide as an electrophilic functionalization. The corresponding ring-opening reaction resulted to be regio- and stereoselective affording to novel phenylselenium-substituted steroids. Assessment of their antibacterial properties against multidrug-resistant bacteria, such as Pseudomonas aeruginosa Xen 5 strain, indicates an interesting bactericidal activity and their ability to prevent bacterial biofilm formation.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Jastrzębska

Mellea

Salerno

et al. 2019

IJMS

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“…The cholesterol epoxides 3 were obtained by a previously optimized methodology involving asymmetric epoxidation of a double bound. 4 …”

Section: Resultsmentioning

confidence: 99%

Synthesis of selenium linked steroidal glycoconjugates

Affeldt¹,

Soares²,

Rodrigues³

et al. 2013

Proceedings of the 15th Brazilian Meeting on Organic Synthesis Proceedings

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“…TNBS was purchased from Sigma (St. Louis, MO). p‐chloro‐phenyl‐selenoesterol (PCS) was prepared according to the method described by Rodrigues et al []. Analysis of the 1H nuclear magnetic resonance (NMR) and 13C NMR spectra showed that the obtained PCS presented analytical and spectroscopic data in full agreement with its assigned structure.…”

Section: Methodsmentioning

confidence: 99%

“…The combination of oxysterols and selenium is rare, and the designed syntheses of these compounds have a great potential to create a new array of molecules with pharmacological activities [Rodrigues et al, ]. p‐chloro‐phenyl‐selenoesterol (PCS) has already been acknowledged in the literature for its anti‐inflammatory and antinociceptive properties in thermal and chemical models of nociception [Sari et al, ] and has had anti‐inflammatory and antioxidant actions in different animal models of acute inflammation [Sari et al, ].…”

mentioning

confidence: 99%

Anti‐Inflammatory and Anti‐Oxidant Effects of p‐Chloro‐phenyl‐selenoesterol on TNBS‐Induced Inflammatory Bowel Disease in Mice

Zarzecki

Bortolotto

Poetini

et al. 2016

J of Cellular Biochemistry

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This study aims to investigate the protective effect of p-chloro-phenyl-selenoesterol [PCS; 0,2 mg/kg; 10 ml/kg i.g.) in colitis induced by 2,4,6-trinitrobenzene sulfonic acid [TNBS; 2 mg/100 µl 50% ethanol; intrarectally) in mice. Several parameters including weight, length, histological analyses determination, thiobarbituric acid reactive species, reactive species levels, superoxide dismutase, catalase, and myeloperoxidase (MPO) activity of colon were evaluated. The serum levels of tumor necrosis factor alpha [TNF-α) and interleukin 6 [IL-6) were also assessed. Treatment with PCS reduced the clinical and histopathologic severity of TNBS-induced colitis, characterized by colon length reduction and increased colon weight and microscopic intestinal inflammation. The therapeutic effects of PCS in this model were associated with significant decrease in proinflammatory cytokines TNF-α and IL-6 and decrease in MPO activity. Furthermore, combined with improvements in inflammatory parameters, treatment with the PCS was able to decrease oxidative stress and to prevent the decrease in antioxidant defenses in animals with TNBS-induced colitis. This finding suggests that PCS can improve experimental colitis in mice and it could be a potential therapeutic agent for the treatment of patients with IBD. J. Cell. Biochem. 118: 709-717, 2017. © 2016 Wiley Periodicals, Inc.

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Stereoselective synthesis of selenosteroids

Cited by 26 publications

References 23 publications

PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

PhSeZnCl in the Synthesis of Steroidal β-Hydroxy-Phenylselenides Having Antibacterial Activity

Synthesis of selenium linked steroidal glycoconjugates

Anti‐Inflammatory and Anti‐Oxidant Effects of p‐Chloro‐phenyl‐selenoesterol on TNBS‐Induced Inflammatory Bowel Disease in Mice

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