Biologically significant selenium-containing heterocycles

Ninomiya, Masayuki; Garud, Dinesh R.; Koketsu, Mamoru

doi:10.1016/j.ccr.2011.07.009

Cited by 152 publications

(70 citation statements)

References 206 publications

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“…Selenium atom is also included in very important components of the human body such as selenoproteins 29 , and glutathione peroxidase-a key enzyme in antioxidant defense 30 . One of the most well known anti-cancer drugs containing a selenium atom is selenazofurin (2-b-Dribofuranosylselenazole-4-carboxamide), five to ten times more potent in in vitro and in vivo anti-tumor screenings than thiazofurin 31 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles

Łączkowski

Biernasiuk

Baranowska-Łączkowska

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis and investigation of antimicrobial activity of 22 novel thiazoles and selenazoles derived from dihydro-2H-thiopyran-4(3H)-one are presented. Additionally, anticonvulsant activity of six derivatives is examinated. Among the derivatives, compounds 4a-f, 4i, 4k, 4 l, 4n, 4o-s and 4v have very strong activity against Candida spp. with MIC ¼ 1.95-15.62 mg/ml. In the case of compounds 4a-f, 4i, 4k, 4 l, 4n, 4o, 4r and 4s, the activity is very strong against some strains of Candida spp. isolated from clinical materials, with MIC ¼ 0.98 to 15.62 mg/ml. Additionally, compounds 4n-v are found to be active against Gram-positive bacteria with MIC ¼ 7.81-62.5 mg/ml. The results of anticonvulsant screening reveal that compounds 4a, 4b, 4m and 4n demonstrate a statistically significant anticonvulsant activity in the pentylenetetrazole model, whereas compounds 4a and 4n showed protection in 6-Hz psychomotor seizure model. Noteworthy, none of these compounds impaired animals' motor skills in the rotarod test. We also performed quantum chemical calculation of interaction and binding energies in complex of 4a with cyclodextrin.

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Section: Introductionmentioning

confidence: 99%

Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles

Łączkowski

Biernasiuk

Baranowska-Łączkowska

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Carboxylic acids bearing strong electron-donating (NPh 2 )a nd withdrawing (NO 2 )g roups as well as an aryliodide function were readily converted to the corresponding thiazoles (1s-1u, 1f)ingood to excellent yields.C ompound 1f (X = I) was subsequently converted to alkynylated derivatives 1v and 1w using the Sonogashira coupling reaction. Selenazole 9, [15] which was hardly accessible,w as similarly synthesized from the carboxylic acid with the assistance of Woollins reagent [16] in moderate yield.…”

mentioning

confidence: 99%

Fluorophores for Excited‐State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids

Tong

Zhao

et al. 2017

Angewandte Chemie

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Discovery of new chemical reactivity of ag iven functional group can often result in innovative synthesis of important chemical entities that possess unprecedented properties.W ed esigned and developed ao ne-step synthesis of 5amino-4-carboxamidothiazoles 1 by an yttrium-triflate-catalyzed reaction of thiocarboxylic acids 2 with isocyanides 3.In this reaction, both reactants 2 and 3 deviated from their normal reactivities because of metal coordination. The resulting heterocycles are novel prototypical structures for the double ESIPT process.S ome of them were excited by visible light irradiation and emitted fluorescence at the NIR region with large Stokes shift, high quantum yield, and strong solvatochromism.

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“…Some organoselenium derivatives show a wide range of pharmacological [1][2][3][4] and biological properties [5][6][7]. Synthesis of new selenium-containing reagents particularly enhances the possibilities of the preparation of previously unknown organic substances [8].…”

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confidence: 99%

Ethyl 3-amino-3-selenoxopropanoate as a new reagent for the synthesis of selenium-containing heterocycles

Dyachenko

2015

Russ J Gen Chem

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Interaction of ethyl cyanoacetate with hydrogen selenide afforded new reagent for obtaining selenium-containing heterocycles such as ethyl 3-amino-3-selenoxopropanoate. Starting from the latter substituted selenazoles and ethyl 3-selenoxo-2,3,5,6,7,8-hexahydroisiquinoline-4-carboxylates were synthesized. The structure of the obtained compounds was confirmed by IR, NMR spectroscopy and gas chromatography-mass spectrometry.

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Biologically significant selenium-containing heterocycles

Cited by 152 publications

References 206 publications

Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles

Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles

Fluorophores for Excited‐State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids

Ethyl 3-amino-3-selenoxopropanoate as a new reagent for the synthesis of selenium-containing heterocycles

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