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Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions.
J Enzyme Inhib Med Chem. 2016; 31(sup2):79-85.JE

Abstract

A series of diaryl ethers were synthesized and their human (h) carbonic anhydrase (CA) isoenzymes hCA I and II, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) inhibitory actions were investigated. The new compounds were synthesized from the corresponding phenols and bromobenzenes via the Ullmann reaction, by using dipicolinic acid as a copper (I) complexing ligand. hCA I and II were inhibited with Kis in the low nanomolar range of 102.01-127.13 nM against hCA I, and of 73.71-113.40 nM against hCA II, whereas the inhibition constants against AChE were of 15.35-18.34 nM and against BChE in the range of 9.07-22.90 nM. The CA inhibition mechanism with these ethers is unknown, but may be similar to that of aryl methyl ethers investigated earlier by computational approaches.

Authors+Show Affiliations

a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey.a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey.a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey. b Department of Zoology , College of Science, King Saud University , Riyadh , Saudi Arabia.a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey.a Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey.c Dipartimento di Chimica Ugo Schiff, Universita degli Studi di Firenze , Sesto Fiorentino , Firenz , Italy , and. d Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences, Universita degli Studi di Firenze , Sesto Fiorentino , Florence , Italy.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27241224

Citation

Özbey, Fadime, et al. "Synthesis of Diaryl Ethers With Acetylcholinesterase, Butyrylcholinesterase and Carbonic Anhydrase Inhibitory Actions." Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 31, no. sup2, 2016, pp. 79-85.
Özbey F, Taslimi P, Gülçin İ, et al. Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. J Enzyme Inhib Med Chem. 2016;31(sup2):79-85.
Özbey, F., Taslimi, P., Gülçin, İ., Maraş, A., Göksu, S., & Supuran, C. T. (2016). Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(sup2), 79-85.
Özbey F, et al. Synthesis of Diaryl Ethers With Acetylcholinesterase, Butyrylcholinesterase and Carbonic Anhydrase Inhibitory Actions. J Enzyme Inhib Med Chem. 2016;31(sup2):79-85. PubMed PMID: 27241224.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. AU - Özbey,Fadime, AU - Taslimi,Parham, AU - Gülçin,İlhami, AU - Maraş,Ahmet, AU - Göksu,Süleyman, AU - Supuran,Claudiu T, Y1 - 2016/05/31/ PY - 2016/6/1/pubmed PY - 2017/2/15/medline PY - 2016/6/1/entrez KW - Acetylcholinesterase KW - butyrylcholinesterase KW - carbonic anhydrase KW - diaryl ethers KW - enzyme inhibition SP - 79 EP - 85 JF - Journal of enzyme inhibition and medicinal chemistry JO - J Enzyme Inhib Med Chem VL - 31 IS - sup2 N2 - A series of diaryl ethers were synthesized and their human (h) carbonic anhydrase (CA) isoenzymes hCA I and II, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) inhibitory actions were investigated. The new compounds were synthesized from the corresponding phenols and bromobenzenes via the Ullmann reaction, by using dipicolinic acid as a copper (I) complexing ligand. hCA I and II were inhibited with Kis in the low nanomolar range of 102.01-127.13 nM against hCA I, and of 73.71-113.40 nM against hCA II, whereas the inhibition constants against AChE were of 15.35-18.34 nM and against BChE in the range of 9.07-22.90 nM. The CA inhibition mechanism with these ethers is unknown, but may be similar to that of aryl methyl ethers investigated earlier by computational approaches. SN - 1475-6374 UR - https://www.unboundmedicine.com/medline/citation/27241224/Synthesis_of_diaryl_ethers_with_acetylcholinesterase_butyrylcholinesterase_and_carbonic_anhydrase_inhibitory_actions_ L2 - http://www.tandfonline.com/doi/full/10.1080/14756366.2016.1189422 DB - PRIME DP - Unbound Medicine ER -