Synthesis, structure and cytotoxicity of 3-C, N, S, Se substituted benzo[b]selenophene derivatives

Arsenyan, Pavel; Paegle, Edgars; Belyakov, Sergey; Шестакова, И.; Jaschenko, Elina; Домрачева, Илона; Popelis, J.

doi:10.1016/j.ejmech.2011.05.008

Cited by 53 publications

(14 citation statements)

References 25 publications

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“…One of our main research interests is the discovery of promising selenium-containing antiproliferative agents. [7,16] In this context,e specially impressive resultsw ere obtained by synthesizing the seleniuma nalogue of raloxifene( aw ell-known selective estrogen-receptor modulator). [7] Thus, the replacement of the sulfur atom by as elenium atom led to ah ighly pronounceda ntiproliferative effect against malignant cell lines and considerably lower basal toxicity.…”

Section: Radical-scavenging Activity and In Vitro Cytotoxicitymentioning

confidence: 99%

Natural‐Antioxidant‐Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity

Paegle

Домрачева

Turovska

et al. 2016

Chemistry An Asian Journal

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The cyclization of arylalkynes under selenobromination conditions, combined with an acid-induced 3,2-aryl shift, was elaborated as a general synthetic pathway for the preparation of polyhydroxy-2- and -3-arylbenzo[b]selenophenes from the same starting materials. The redox properties, free-radical-scavenging ability, and cytotoxicity against malignant cell lines (MCF-7, MDA-MB-231, HepG2, and 4T1) of the synthesized compounds were explored, and the obtained results were used to consider the structure-activity relationships (SARs) in these compounds. Consequently, the structural features that were responsible for the highly potent peroxyl-radical-scavenging activity were established.

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Section: Radical-scavenging Activity and In Vitro Cytotoxicitymentioning

confidence: 99%

Natural‐Antioxidant‐Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity

Paegle

Домрачева

Turovska

et al. 2016

Chemistry An Asian Journal

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“…Arsenyan group examined in 2011 the reactivity of a 3‐bromobenzoselenophene with HetArSnR 3 in the presence of 4 mol % Pd(PPh 3 ) 4 associated to 7 mol % AsPh 3 in xylene (Scheme , top) . This method allowed to introduce thienyl or pyridyl groups at C3‐position of benzoselenophene.…”

Section: C3‐arylation Of Selenophenesmentioning

confidence: 99%

“…Arsenyan group also examined the reactivity of a 2‐substituted 3‐bromobenzoselenophene in the presence of (hetero)arylboronic acids (Scheme , middle). They employed 10 mol % Pd(OAc) 2 associated to 20 mol % P( o ‐tol) 3 as catalyst and K 3 PO 4 as base, and obtained the C3‐arylated benzoselenophenes in good yields, including with two heteroarenes: a 2‐pyridineboronic acid and a 3‐thiopheneboronic acid . In 2014 and 2016, they extended this procedure to fluoro‐substituted benzoselenophenes (Scheme , bottom)…”

Section: C3‐arylation Of Selenophenesmentioning

confidence: 99%

Access to (Hetero)arylated Selenophenes via Palladium‐catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

et al. 2017

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(Hetero)aryl‐substituted selenophenes exhibit important physical properties especially for optoelectronics. Palladium‐catalysed coupling reactions currently represent the most efficient methods to prepare such (hetero)arylated selenophene derivatives. Initially, Stille coupling was the most efficient reaction for the synthesis of these compounds; however, over the last decade, Suzuki coupling has become the most commonly employed. Recently, Pd‐catalysed arylation via the C−H bond activation of selenophenes has proved to be a very convenient alternative method for the preparation of several arylated selenophenes as there is no need to prepare organometallic derivatives. In this Review, the progress and substrate scope in the synthesis of both C2‐ and C3‐arylated selenophenes via Pd‐catalysis are summarized.

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“…In particular, the benzo[ b ]selenophenes have attracted increasing attention in the last decade as a result of its promising application in medicinal chemistry and new materials . Benzo[ b ]selenophene derivatives present cytotoxic and antioxidant activities. The Se‐analogue of raloxifene, for example, is an antiproliferative agent in the treatment of breast cancer (Scheme ) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

et al. 2017

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A convenient synthesis of 1‐(2‐organylchalcogenylethynyl)‐2‐butylselenanylbenzenes was established taking advantage of the selective reaction of 1‐(2,2‐dibromovinyl)‐2‐butylselenanylbenzenes with thiols or diorganyl diselenides. The new 1‐(2‐chalcogenylethynyl)‐2‐butylselenanylbenzenes were prepared in good yields and used as precursors of 2‐organylchalcogenylbenzo[b]selenophenes via electrophilic cyclization using I2, Br2 or PhSeBr as electrophiles. Different classes of new 3‐substituted‐ (3‐iodo, 3‐bromo, 3‐phenylselenanyl) benzo[b]selenophenes were prepared in good yields. The synthetic application of the obtained products was demonstrated employing the benzo[b]selenophenes in Suzuki and Sonogashira cross‐coupling reactions.

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Synthesis, structure and cytotoxicity of 3-C, N, S, Se substituted benzo[b]selenophene derivatives

Cited by 53 publications

References 25 publications

Natural‐Antioxidant‐Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity

Natural‐Antioxidant‐Inspired Benzo[b]selenophenes: Synthesis, Redox Properties, and Antiproliferative Activity

Access to (Hetero)arylated Selenophenes via Palladium‐catalysed Stille, Negishi or Suzuki Couplings or C−H Bond Functionalization Reaction

Synthesis of 2‐Organylchalcogenyl–benzo[b]selenophenes: 1‐(2,2‐Dibromovinyl)‐2‐butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization

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