Yazarlar

• Coskun, Ahmet(1)
• Dastan, Arif(1)
• Ecer, Kadriye(1)
• Erdem, Safiye S.(1)
• Gülçin, Ilhami(1)
• Güney, Murat(1)
• Kaya, Afşin A.(1)
• Menzek, Abdullah(1)
• Salamci, Emine(1)
• Supuran, Claudiu T.(1)
• Topal, Fevzi(1)
• Şahin, Ertan(1)

• MakaleAçık Erişim2017Scopus SJRQ2/r/gumushane/11341
  Reaction of 9-oxabicyclo[4.2.1]non-7-ene-1-ol with tetrazine: An unusually facile intramolecular rearrangement

  Kaya, Afşin A.; Salamci, Emine; Menzek, Abdullah; Erdem, Safiye S.; Şahin, Ertan; Ecer, Kadriye

  Reaction of (1S*,7R*)-9-oxabicyclo[4.2.1]non-7-en-1-ol (5) with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (6) produced (2R*,4R*)-dimethyl 4-(7-oxooxepan-2-yl)-1,4-dihydropyridazine-3,6-dicarboxylate (11) in a one-pot reaction involving cycloaddition at ambient conditions. The structure of the rearrangement product 11 was determined by X-ray crystallographic analysis. Its formation was discussed based on experimental studies and density functional theory calculations. The driving force of this unusually facile reaction was the stability of the caprolactone product 11 and the extremely exorgenic loss of N2. Structural factors facilitating this rearrangement were also explored employing PCM//M06-2X/6-31G(d, p) calculations.

  AtıfScopus22·WoS17·OpenAlex22

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• MakaleAçık Erişim2014Scopus SJRQ1/r/gumushane/10328
  Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives

  Güney, Murat; Coskun, Ahmet; Topal, Fevzi; Dastan, Arif; Gülçin, Ilhami; Supuran, Claudiu T.

  The oxidation of some cyanocycloheptatrienes with CrO3 and pyridine was investigated and a few new nitrile functionalised benzotropone derivatives were obtained. Photooxygenation reaction of these products was also studied. The structures of the formed products were determined on the basis of NMR spectroscopy and the formation mechanism of unusual products was discussed. Human carbonic anhydrase isoenzymes I, and II (hCA I and hCA II) inhibition properties of nitrile functionalized new benzotropone derivatives were also studied. Both CA isozymes were inhibited in the low micromolar range by these nitrile functionalized benzotropone analogues. The newly synthesized benzotropone derivatives showed inhibition constants in the sub-micromolar range (2.51-4.06 mu M). The best hCA I inhibition was observed in 5H-benzocycloheptene-7-carbonitrile (K-1: 2.88 +/- 0.86 mu M). On the other hand, 5-oxo-5H-benzocycloheptatriene-7-carbonitrile showed the powerful inhibitory effect against hCA II (K-i: 2.51 +/- 0.34 mu M). (C) 2014 Elsevier Ltd. All rights reserved.

  AtıfScopus128·WoS132·OpenAlex127

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