Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives

Guney, Murat; Coskun, Ahmet; TOPAL, Fevzi; Daştan, Arif; Gülçin, İlhami; SUPURAN, Claudiu T.

doi:10.1016/j.bmc.2014.04.007

Makale Tam Makale Uluslararası 2014

Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives

Murat Guney, Ahmet Coskun, Fevzi TOPAL, Arif Daştan, İlhami Gülçin, Claudiu T. SUPURAN

BIOORGANIC & MEDICINAL CHEMISTRY Cilt 22 · Sayı 13 · ss. 3537–3543 · 01.07.2014

DOI ile aç

Özet

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.

Anahtar kelimeler

antioxidant SULFONAMIDE DERIVATIVES ISOFORMS I VITRO CARBONIC-ANHYDRASE INHIBITION ERYTHROCYTE ISOZYMES I oxidation benzotropone Rearrangement BICYCLIC ENDOPEROXIDES CYCLOADDITION REACTIONS singlet oxygen Benzocycloheptatriene Nitrile-substituted drugs ANTITUMOR AGENTS ESTER ANALOGS

Atıf için künye

Guney, M., Coskun, A., TOPAL, F., Daştan, A., Gülçin, İ., & SUPURAN, C. T. (2014). Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives. BIOORGANIC & MEDICINAL CHEMISTRY, 22(13), 3537–3543. https://doi.org/10.1016/j.bmc.2014.04.007

BibTeX

@article{guney2014-67645,
  author = {Guney, Murat and Coskun, Ahmet and TOPAL, Fevzi and Daştan, Arif and Gülçin, İlhami and SUPURAN, Claudiu T.},
  title = {Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives},
  journal = {BIOORGANIC & MEDICINAL CHEMISTRY},
  year = {2014},
  volume = {22},
  number = {13},
  pages = {3537--3543},
  issn = {0968-0896},
  doi = {10.1016/j.bmc.2014.04.007},
  url = {https://akademik.atauni.edu.tr/yayinlar/67645-oxidation-of-cyanobenzocycloheptatrienes-synthesis-photooxygenation-reaction-and}
}