Synthesis of diaryl ethers with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions

被引：118
作者：
Ozbey, Fadime [1 ]
Taslimi, Parham [1 ]
Gulcin, Ilhami [1 ,2 ]
Maras, Ahmet [1 ]
Goksu, Sueleyman [1 ]
Supuran, Claudiu T. [3 ,4 ]
机构：
[1] Ataturk Univ, Dept Chem, Fac Sci, Erzurum, Turkey
[2] King Saud Univ, Dept Zool, Coll Sci, Riyadh, Saudi Arabia
[3] Univ Firenze, Dipartimento Chim Ugo Schiff, Florence, Italy
[4] Univ Firenze, Sect Pharmaceut & Nutriceut Sci, Neurofarba Dept, Florence, Italy
来源：
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2016年 / 31卷
关键词：
Acetylcholinesterase; butyrylcholinesterase; carbonic anhydrase; diaryl ethers; enzyme inhibition; TROUT ONCORHYNCHUS-MYKISS; ERYTHROCYTES IN-VITRO; ISOENZYMES HCA I; BIOLOGICAL EVALUATION; BROMOPHENOL DERIVATIVES; SULFONAMIDE DERIVATIVES; ENZYME-ACTIVITY; ISOZYMES I; VIVO; ANTIOXIDANT;
D O I：
10.1080/14756366.2016.1189422
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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 K(i)s in the low nanomolar range of 102.01-127.13nM against hCA I, and of 73.71-113.40nM against hCA II, whereas the inhibition constants against AChE were of 15.35-18.34nM and against BChE in the range of 9.07-22.90nM. The CA inhibition mechanism with these ethers is unknown, but may be similar to that of aryl methyl ethers investigated earlier by computational approaches.
引用
收藏
页码：79 / 85
页数：7
相关论文
共 82 条
[1]   Synthesis and Carbonic Anhydrase Inhibitory Effects of Novel Sulfamides Derived from 1-Aminoindanes and Anilines [J].
Akbaba, Yusuf ;
Bastem, Enes ;
Topal, Fevzi ;
Gulcin, Ilhami ;
Maras, Ahmet ;
Goksu, Suleyman .
ARCHIV DER PHARMAZIE, 2014, 347 (12) :950-957
[2]   Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins [J].
Akbaba, Yusuf ;
Akincioglu, Akin ;
Gocer, Hulya ;
Goksu, Suleyman ;
Gulcin, Ilhami ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2014, 29 (01) :35-42
[3]   Synthesis and Biological Evaluation of Novel Bromophenol Derivatives as Carbonic Anhydrase Inhibitors [J].
Akbaba, Yusuf ;
Balaydin, Halis Turker ;
Menzek, Abdullah ;
Goksu, Suleyman ;
Sahin, Ertan ;
Ekinci, Deniz .
ARCHIV DER PHARMAZIE, 2013, 346 (06) :447-454
[4]   Discovery of potent carbonic anhydrase and acetylcholine esterase inhibitors: Novel sulfamoylcarbamates and sulfamides derived from acetophenones [J].
Akincioglu, Akin ;
Akincioglu, Hulya ;
Gulcin, Ilhami ;
Durdagi, Serdar ;
Supuran, Claudiu T. ;
Goksu, Suleyman .
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (13) :3592-3602
[5]   Novel Sulphamides and Sulphonamides Incorporating the Tetralin Scaffold as Carbonic Anhydrase and Acetylcholine Esterase Inhibitors [J].
Akincioglu, Akin ;
Topal, Meryem ;
Guelcin, Ilhami ;
Goeksu, Sueleyman .
ARCHIV DER PHARMAZIE, 2014, 347 (01) :68-76
[6]   Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors [J].
Akincioglu, Akin ;
Akbaba, Yusuf ;
Gocer, Hulya ;
Goksu, Suleyman ;
Gulcin, Ilhami ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (06) :1379-1385
[7]   Acetylcholinesterase Inhibitory and Antioxidant Activities of Novel Symmetric Sulfamides Derived from Phenethylamines [J].
Aksu, Kadir ;
Topal, Fevzi ;
Gulcin, Ilhami ;
Tumer, Ferhan ;
Goksu, Suleyman .
ARCHIV DER PHARMAZIE, 2015, 348 (06) :446-455
[8]   Synthesis and carbonic anhydrase inhibitory properties of sulfamides structurally related to dopamine [J].
Aksu, Kadir ;
Nar, Meryem ;
Tanc, Muhammet ;
Vullo, Daniela ;
Gulcin, Ilhami ;
Goksu, Suleyman ;
Tumer, Ferhan ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (11) :2925-2931
[9]   Capsaicin: A Potent Inhibitor of Carbonic Anhydrase Isoenzymes [J].
Arabaci, Betul ;
Gulcin, Ilhami ;
Alwasel, Saleh .
MOLECULES, 2014, 19 (07) :10103-10114
[10]   Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo [J].
Aras-Hisar, S ;
Hisar, O ;
Beydemir, S ;
Gülcin, I ;
Yanik, T .
ACTA VETERINARIA HUNGARICA, 2004, 52 (04) :413-422
123456789