Synthesis of 4,5-disubstituted-2-thioxo-1,2,3,4-tetrahydropyrimidines and investigation of their acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase I/II inhibitory and antioxidant activities

被引：133

作者：

Garibov, Emin ^{[1
]}

Taslimi, Parham ^{[2
]}

Sujayev, Afsun ^{[1
]}

Bingol, Zeynebe ^{[2
]}

Cetinkaya, Songul ^{[2
]}

Gulcin, Ilhami ^{[2
,3
]}

Beydemir, Sukru ^{[2
]}

Farzaliyev, Vagif ^{[1
]}

Alwasel, Saleh H. ^{[2
]}

Supuran, Claudiu T. ^{[4
,5
]}

机构：

[1] Azerbaijan Natl Acad Sci, Inst Chem Addit, Lab Theoret Bases Synth & Act Mech Addit, Baku, Azerbaijan

[2] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey

[3] King Saud Univ, Dept Zool, Coll Sci, Riyadh, Saudi Arabia

[4] Univ Firenze, Dipartimento Chim Ugo Schiff, Florence, Sesto Fiorentin, Italy

[5] Univ Firenze, Sect Pharmaceut & Nutriceut Sci, Neurofarba Dept, Florence, Sesto Fiorentin, Italy

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2016年 / 31卷

关键词：

Acetylcholinesterase; antioxidant activity; butyrylcholinesterase; carbonic anhydrase; enzyme inhibition; IN-VITRO ANTIOXIDANT; LYOPHILIZED AQUEOUS EXTRACT; RADICAL SCAVENGING ACTIVITY; ERYTHROCYTE ISOZYMES I; ISOENZYMES HCA I; ANTIRADICAL ACTIVITIES; POLYPHENOL CONTENTS; SULFONAMIDE DERIVATIVES; L; ESTERASE;

D O I：

10.1080/14756366.2016.1198901

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 tetrahydropyrimidinethiones were synthesized from thiourea, -diketones and aromatic aldehydes, such as p-tolualdehyde, p-anisaldehyde, o-tolualdehyde, salicylaldehyde and benzaldehyde. These cyclic thioureas showed good inhibitory action against acetylcholine esterase (AChE), butyrylcholine esterase (BChE), and human (h) carbonic anhydrase (CA) isoforms I and II. AChE and BChE inhibitions were in the range of 6.11-16.13 and 6.76-15.68nM, respectively. hCA I and II were effectively inhibited by these compounds, with K-i values in the range of 47.40-76.06nM for hCA I, and of 30.63-76.06nM for hCA II, respectively. The antioxidant activity of the cyclic thioureas was investigated by using different in vitro antioxidant assays, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, Cu(2+)and Fe(3+)reducing, and Fe(2+)chelating activities.

引用

页码：1 / 9

页数：9

共 123 条

[1] An improved synthesis of Biginelli-type compounds via phase-transfer catalysis [J].

Ahmed, Bahar ;

Khan, Riaz A. ;

Habibullah ;

Keshari, Manoj .

TETRAHEDRON LETTERS, 2009, 50 (24) :2889-2892

[2] Antioxidant and radical scavenging properties of curcumin [J].

Ak, Tuba ;

Gulcin, Ilhami .

CHEMICO-BIOLOGICAL INTERACTIONS, 2008, 174 (01) :27-37

[3] 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

[4] 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

[5] Isatin analogs as novel inhibitors of Candida spp. β-carbonic anhydrase enzymes [J].

Akdemir, Atilla ;

Guzel-Akdemir, Ozlen ;

Karali, Nilgun ;

Supuran, Claudiu T. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (08) :1648-1652

[6] 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

[7] 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

[8] 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

[9] 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

[10] Carbonic anhydrase IX correlates with survival and is a potential therapeutic target for neuroblastoma [J].

Ameis, Helen M. ;

Drenckhan, Astrid ;

Freytag, Morton ;

Izbicki, Jakob R. ;

Supuran, Claudiu T. ;

Reinshagen, Konrad ;

Holland-Cunz, Stefan ;

Gros, Stephanie J. .

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 (03) :404-409

← 1 2 3 4 5 6 7 8 9 10 →