New selenium-containing acetylenic retinoids by direct coupling of alkynylsilanes with selenylhalides

Diaz, Philippe; Gendre, Fabrice; Bernardon, Jean-Michel

doi:10.1016/s0040-4039(98)02038-3

Cited by 16 publications

(7 citation statements)

References 11 publications

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“…The quantum yields of 1 O 2 production by selenium compounds (338)(339)(340)(341)(342)(343) are much higher than that by psoralen (343). 287 The introduction of selenium for oxygen is also expected to lead to a higher triplet quantum yield and a reduced lifetime of the electronically excited states due to the heavy atom effect 288 and a slightly different geometry.…”

Section: Photochemotherapeutic Agentsmentioning

confidence: 99%

Chemistry of Biologically Important Synthetic Organoselenium Compounds

2001

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Section: Photochemotherapeutic Agentsmentioning

confidence: 99%

Chemistry of Biologically Important Synthetic Organoselenium Compounds

2001

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“…Some aromatic R-benzylactones bearing a seleno substituent such as 45 and 46 were found to be inhibitors of human colon 8r cell proliferation [193]. However, these Se analogues offered no advantage in terms of efficacy or toxicity over the parent compounds.…”

Section: Selenium Derivatives Of Potential Antitumor Activitymentioning

confidence: 99%

Selenium Derivatives as Cancer Preventive Agents

Aboul‐Fadl

2005

CMCACA

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The role of selenium in the prevention of cancer has been recently established by laboratory experiments, clinical trials, and epidemiological data. Most of the effects are related to the function of selenium in antioxidant enzyme systems. Animal data, epidemiological data, and intervention trials have shown a clear role for selenium derivatives in both prevention of specific cancers and antitumorigenic effects in postinitiation phases of cancer. Consequently, selenium supplementation has moved from the realm of correcting nutritional deficiencies to one of pharmacological intervention, especially in the clinical domain of cancer chemoprevention. Accordingly, there has been substantial interest directed toward the synthesis of selenium-containing derivatives in recent years that could be used as cancer chemopreventive agents. The current review aims to outline recent developments in the application of selenium derivatives as cancer preventive agents.

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“…However, all these properties belong to organoselenides due to their ability to engage in enzymatic processes [4–5] and alkynyl selenides have demonstrated only limited biological properties [6–7]. On the other hand, these compounds are widely applied in organic chemistry due to the presence of an alkynyl group [8–9] and an organoselenium moiety [10] in one molecule both comprising versatile building blocks or intermediates in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…Alkynyl selenides, as many other selenium compounds, have potential anti-oxidant activities, and may play a role in certain diseases such as cancer, heart diseases, inflammatory processes, arthritis, and skin damage caused by exposure to UV radiation [ 1 – 3 ]. However, all these properties belong to organoselenides due to their ability to engage in enzymatic processes [ 4 – 5 ] and alkynyl selenides have demonstrated only limited biological properties [ 6 – 7 ]. On the other hand, these compounds are widely applied in organic chemistry due to the presence of an alkynyl group [ 8 – 9 ] and an organoselenium moiety [ 10 ] in one molecule both comprising versatile building blocks or intermediates in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

Heredia¹,

Peñéñory²

2017

Beilstein J. Org. Chem.

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Alkynyl selenides were synthesized by a straightforward one-pot and three-step methodology, without the need of diselenides as starting reagents, under an oxygen atmosphere and using PEG 200 as the solvent. This procedure involves the in situ generation of dialkyl diselenides through a K3PO4-assisted reaction of an alkyl selenocyanate obtained by a nucleophilic substitution reaction between KSeCN and alkyl halides. Successive reaction with terminal alkynes in the presence of t-BuOK affords the corresponding alkyl alkynyl selenide in moderate to good yields. Finally, this methodology allowed the synthesis of 2-alkylselanyl-substituted benzofuran and indole derivatives starting from convenient 2-substituted acetylenes.

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New selenium-containing acetylenic retinoids by direct coupling of alkynylsilanes with selenylhalides

Cited by 16 publications

References 11 publications

Chemistry of Biologically Important Synthetic Organoselenium Compounds

Chemistry of Biologically Important Synthetic Organoselenium Compounds

Selenium Derivatives as Cancer Preventive Agents

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

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