期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 22, 期 13, 页码 3537-3543出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2014.04.007
关键词
Benzocycloheptatriene; Benzotropone; Oxidation; Rearrangement; Nitrile-substituted drugs; Carbonic anhydrase inhibition
资金
- TUBITAK [104T401]
- Ataturk University
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.
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