Novel sulfamate derivatives of menthol: Synthesis, characterization, and cholinesterases and carbonic anhydrase enzymes inhibition properties

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Daryadel S., Atmaca U., Taslımı P., Gülçin İ., Çelik M.

ARCHIV DER PHARMAZIE, cilt.351, sa.11, 2018 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 351 Sayı: 11
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1002/ardp.201800209
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase, enzyme inhibition, sulfamate, INCLUDING NATURAL-PRODUCTS, GLUTATHIONE-S-TRANSFERASE, ISOENZYMES I, ACETYLCHOLINE ESTERASE, CRYSTAL-STRUCTURE, 1ST SYNTHESIS, HCA I, BUTYRYLCHOLINESTERASE, BROMOPHENOLS, ANTIOXIDANT
  • Atatürk Üniversitesi Adresli: Evet

Özet

Sulfamates have a large spectrum of biological activities including enzyme inhibition. Eight sulfamates derived from menthol (2a-h) were synthesized. Also, in the other section of this study, novel sulfamate derivatives of menthol were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and carbonic anhydrase I and II enzymes (hCAs I and II). The newly synthesized novel menthol sulfamate and menthol carbonyl sulfamate derivatives showed K-i values in the range of 34.37 +/- 8.17 to 53.40 +/- 10.61 nM against hCA I, 12.91 +/- 4.57 to 38.67 +/- 6.22 nM against hCA II, 111.17 +/- 52.36 to 522.86 +/- 120.08 nM against AChE, and 50.01 +/- 11.73 to 109.63 +/- 50.08 nM against BChE. As a result, the novel menthol sulfamate and menthol carbonyl sulfamate derivatives can be promising Alzheimer's disease drug candidates and novel hCA I and hCA II enzymes inhibitors.