Selenium- and tellurium-containing redox modulators with distinct activity against macrophages: possible implications for the treatment of inflammatory diseases

Doering, Mandy; Diesel, Britta; Gruhlke, Martin C. H.; Viswanathan, Uma M.; Mániková, Dominika; Chovanec, Miroslav; Burkholz, Torsten; Slusarenko, Alan; Kiemer, Alexandra K.; Jacob, Claus

doi:10.1016/j.tet.2012.09.021

Cited by 32 publications

(32 citation statements)

References 48 publications

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“…The results in Table 1 show that with the elemental iron, Fe(acac) 3 , Fe 2 O 3 , Fe 2 (SO 4 ) 3 .xH 2 O the reaction did not proceed and the starting material was recovered (Table 1, entries [11][12][13][14]. The catalyst screening also revealed that ferrous chloride tetrahydrate and ferric chloride hexahydrate catalyzed the cyclization of 1a as efficiently as anhydrous iron(III) chloride ( 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 5 21).…”

Section: Resultsmentioning

confidence: 99%

“…Yield: 0.114 g (86%); mp 125.6−127.0 °C. 2H), 5.52 (dd, J = 5.4 Hz, J = 3.1 Hz, 1H), 4.75 (dd, J = 12.7 Hz, J = 5.4 Hz, 1H), 4.61 (dd, J = 12.7 Hz, J = 3.1 Hz, 1H), 2.34 (s, 3H), 2.23 (s, 3H) 13. C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm) 138.7, 137.7, 137.6, 135.0, 133.9, …”

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confidence: 99%

“…1H), 3.68−3.62 (m, 1H), 2.33−2.30 (m, 2H). 13 C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm)139.5, 139.3, 136.4, 132.2, 130.0, 129.2, 129.1, 129.0, 5H) 13. C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm) 139.4, 139.1, 128.7, 137.1, 136.5, 132.6, 130.0, 129.9, 129.1, 128.0, 127.3, 126.2, 1H), 2.27−2.24 (m, 2H) 13.…”

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confidence: 99%

“…13 C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm)139.5, 139.3, 136.4, 132.2, 130.0, 129.2, 129.1, 129.0, 5H) 13. C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm) 139.4, 139.1, 128.7, 137.1, 136.5, 132.6, 130.0, 129.9, 129.1, 128.0, 127.3, 126.2, 1H), 2.27−2.24 (m, 2H) 13. C{ 1 H}NMR (CDCl 3 , 100 MHz): δ(ppm) 163.3 (d, J = 249.6 Hz), 162.5 (d, J = 249.6 Hz), 138.9, 138.5 (d, J = 8.0 Hz), 134.9 (d, J = 8.0 Hz), 129.0, 128.3, 128.1 (2C), 124.1 (d, J = 3.3 Hz), 122.8 (d, J HRMS: calcd for C 23 H 19 F 2 OSe 2 (ESI-TOF, M + H + ) 508.9734, found 508.9739.…”

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confidence: 99%

“…Yield: 0.097 g (60%); mp 120.5−122.8 °C. 1 H NMR (CDCl 3 , 400 MHz): δ (ppm) 2H), 9H), 7.03 (t, J = 8.7 Hz, 2H), 2H), 6.87 (t, J = 8.7 Hz, 2H), 5.26 (dd, J = 4.8 Hz, J = 1.6 Hz, 1H), 4.19 (dd, J = 14.8 Hz, J = 1.6 Hz, 1H), 4.12 (dd, J = 14.8 Hz, J = 4.8 Hz, 1H), 2.40 (s, 3H) 13. C{ 1 H}NMR (CDCl 3 , 100 MHz): δ (ppm) 163.3 (d, J = 250.2 Hz), 162.9 (d, J = 250.2 Hz),143.3, 138.7, 137.1 (d, J = 8.1 Hz), SSe 2 (ESI-TOF, M + H + ) 647.9826, found 647.9831.…”

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confidence: 99%

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Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

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An iron-catalyzed system, using diorganyl diselenides as an organoselenium source, was used for the cyclization of 1,4-butyne-diols in the preparation of 3,4-bis(organoselanyl)-2,5-dihydrofurans. The optimized reaction conditions are compatible with many functional groups in 1,4-butyne-diols and diorganyl diselenides. In addition, this catalyst system was also efficient with diorganyl disulfides, but it did not work for diorganyl ditellurides. The same reaction conditions were also extended to pentyne-1,5-diol for the preparation of 4,5-bis(organoselanyl)-3,6-dihydro-2H-pyrans and to 4-amino-butynol for the preparation of 2,5-dihydro-1H-pyrrole derivatives. The synthetic utility of these heterocycles was studied using 5-bis(organoselanyl)-3,6-dihydro-2H-pyrans as substrate in a Kumada-type cross-coupling reaction.

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

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Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part C. Miscellaneous Biological Activities

Braga

Rafique

2014

Patai's Chemistry of Functional Groups

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Organoselenium compounds are known as antioxidants, antithyroid, antinociceptive, antidepressant, thioredoxin reductase (TrxR) mimetic agents with a variety of protective behaviors (e.g. cardioprotective, neuroprotective and hepatoprotective). In addition. they can be used as virueides, bactericides, fungicides, cytokine inducers and immunomodulators. The chemical and biological activity of organose leniumcompounds is discussed herein. The strategies and methods for the preparation of biologically relevant small molecules containing selenium are reviewed in this chapter. The unique redox properties of selenium confer catalytic activity to organoselenium compounds and influence their biological properties as well as the methods selected for their preparation. The approaches available to obtain organoselenium compounds, including reaction of elemental selenium or diselenides with different types of carbanions or reaction of organic electrophiles with selenolate anions generated by different methods, are disclosed in this chapter.

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Iron‐Promoted Tandem Cyclization of 1,3‐Diynyl Chalcogen Derivatives with Diorganyl Dichalcogenides for the Synthesis of Benzo[b]furan‐Fused Selenophenes

et al. 2016

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Ad ouble intramolecular 5-endo-dig cyclization of butyl[2-(phenylbuta-1,3-diynyl)phenyl]chalcogens has been employed in as electivep reparation of benzo[b]chalcogenopheno[2,3-d]furans. Severalr eactionp arameters were studied to determine the best reactionc onditions and we observed that the reactiono fb utyl[2-(phenylbuta-1,3-diynyl)phenyl]chalcogens (0.25 mmol) with iron(III) chloride hexahydrate (2.0 equiv.) and diorganyl diselenides (1.75 equiv.) at reflux of dichloromethane was the most appropriate to give the productsi n3 5-89% yields.T hese standard reactionc onditions were compatible with many functional groups in the substrates,s uch as methyl, chlorine,f luorine,m ethoxy and heteroaryl. This protocolw as also efficient for diorganyl diselenidesb ut it was ineffective with di-organyl disulfidesa nd ditellurides.I nacompetition among selenium, sulfura nd oxygenn ucleophiles we observed that the nucleophilicity and steric effects of the competingf unctional groups were determinant factorsf or the selectivity of the cyclization. Theb enzo[b]chalcogenopheno[2,3-d]furans had absorptions in the UV region (300-350nmr ange) with molar absorptivity coefficient values ascribed to spin and symmetry allowed p-p*e lectronic transitions.A n emission located in the purple region (380-440nm range), with aS tokes shift of between 65-100 nm, is probably associated to the charge transfer character of the excited state.

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Selenium- and tellurium-containing redox modulators with distinct activity against macrophages: possible implications for the treatment of inflammatory diseases

Cited by 32 publications

References 48 publications

Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2H-pyran, and 2,5-Dihydro-1H-pyrrole Organoselanyl Derivatives

Synthesis of Biologically Relevant Small Molecules Containing Selenium. Part C. Miscellaneous Biological Activities

Iron‐Promoted Tandem Cyclization of 1,3‐Diynyl Chalcogen Derivatives with Diorganyl Dichalcogenides for the Synthesis of Benzo[b]furan‐Fused Selenophenes

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