Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives
Küçük Resim Yok
Tarih
2014
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pergamon-Elsevier Science Ltd
Erişim Hakkı
info:eu-repo/semantics/closedAccess
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.
Açıklama
Anahtar Kelimeler
Benzocycloheptatriene, Benzotropone, Oxidation, Rearrangement, Nitrile-Substituted Drugs, Carbonic Anhydrase Inhibition
Kaynak
Bioorganic & Medicinal Chemistry
WoS Q Değeri
Q2
Scopus Q Değeri
Q2
Cilt
22
Sayı
13
