Synthesis of nitrogen, phosphorus, selenium and sulfur-containing heterocyclic compounds - Determination of their carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase and α-glycosidase inhibition properties

被引:85
作者
Gulcin, Ilhami [1 ]
Trofimov, Boris [2 ]
Kaya, Ruya [1 ,3 ]
Taslimi, Parham [4 ]
Sobenina, Lyubov [2 ]
Schmidt, Elena [2 ]
Petrova, Olga [2 ]
Malysheva, Svetlana [2 ]
Gusarova, Nina [2 ]
Farzaliyev, Vagif [3 ]
Sujayev, Afsun [5 ]
Alwasel, Saleh [6 ]
Supuran, Claudiu T. [7 ,8 ,9 ]
机构
[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey
[2] Russian Acad Sci, Siberian Branch, Irkutsk Inst Chem, Irkutsk 664033, Russia
[3] Ibrahim Cecen Univ Agri, Cent Res & Applicat Lab, TR-04100 Agri, Turkey
[4] Bartin Univ, Dept Biotechnol, Fac Sci, TR-74100 Bartin, Turkey
[5] Azerbaijan Natl Acad Sci, Inst Chem Addit, Baku 1029, Azerbaijan
[6] King Saud Univ, Dept Zool, Coll Sci, Riyadh, Saudi Arabia
[7] Univ Firenze, Dipartimento Chim Ugo Schiff, Florence, Italy
[8] Univ Firenze, Neurofarba Dept, Sesto Fiorentino, Italy
[9] Univ Firenze, Lab Chim Bioinorgan, Sesto Fiorentino, Italy
关键词
Pyrrole; Carbonic anhydrase; Enzyme inhibition; alpha-Glycosidase; Acetylcholinesterase; Butyrylcholinesterase; GLUTATHIONE-S-TRANSFERASE; ERYTHROCYTE ISOZYMES I; ISOENZYMES HCA I; ISOFORMS I; ANTICHOLINERGIC PROPERTIES; BIOLOGICAL EVALUATION; 1ST SYNTHESIS; ANTIOXIDANT; DERIVATIVES; SULFAMIDES;
D O I
10.1016/j.bioorg.2020.104171
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
Sulfur-containing pyrroles (1-3), tris(2-pyridyl)phosphine(selenide) sulfide (4-5) and 4-benzyl-6-(thiophen-2-yl)pyrimidin-2-amine (6) were synthesized and characterized by elemental analysis, IR and NMR spectra. In this study, the synthesized compounds of nitrogen, phosphorus, selenium and sulfur-containing heterocyclic compounds (1-6) were evaluated against the human erythrocyte carbonic anhydrase I, and II isoenzymes, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glycosidase enzymes. The synthesized heterocyclic compounds showed IC50 values in range of 33.32-60.79 nM against hCA I, and 37.05-66.64 nM against hCA II closely associated with various physiological and pathological processes. On the other hand, IC50 values were found in range of 13.13-22.21 nM against AChE, 0.54-31.22 nM against BChE, and 13.51-26.55 nM against alpha-glycosidase as a hydrolytic enzyme. As a result, nitrogen, phosphorus, selenium and sulfur-containing heterocyclic compounds (1-6) demonstrated potent inhibition profiles against indicated metabolic enzymes. Therefore, we believe that these results may contribute to the development of new drugs particularly in the treatment of some global disorders including glaucoma, Alzheimer's disease and diabetes.
引用
收藏
页数:9
相关论文
共 36 条
[31]   Cytotoxic effects, carbonic anhydrase isoenzymes, α-glycosidase and acetylcholinesterase inhibitory properties, and molecular docking studies of heteroatom-containing sulfonyl hydrazone derivatives [J].
Celebioglu, Hasan Ufuk ;
Erden, Yavuz ;
Hamurcu, Fatma ;
Taslimi, Parham ;
Senturk, Ozan Sanli ;
Ozmen, Ummuhan Ozdemir ;
Tuzun, Burak ;
Gulcin, Ilhami .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 2021, 39 (15) :5539-5550
[32]   Synthesis of heterocyclic phosphonato esters by reaction between triphenyl phosphite and acetylenic diesters in the presence of sulfur-containing heterocyclic compounds [J].
Aminkhani, Ali ;
Kabiri, Roya ;
Habibi-Khorassani, Sayyed Mostafa ;
Heydari, Reza ;
Maghsoodlou, Malek Taher ;
Marandi, Ghasem ;
Lashkari, Mojtaba ;
Rostamizadeh, Mohsen .
JOURNAL OF SULFUR CHEMISTRY, 2009, 30 (05) :500-506
[33]   Synthesis of novel 5-amino-1,3,4-thiadiazole-2-sulfonamide containing acridine sulfonamide/carboxamide compounds and investigation of their inhibition effects on human carbonic anhydrase I, II, IV and VII [J].
Aday, Burak ;
Ulus, Ramazan ;
Tanc, Muhammet ;
Kaya, Muharrem ;
Supuran, Claudiu T. .
BIOORGANIC CHEMISTRY, 2018, 77 :101-105
[34]   New aromatic/heteroaromatic propanesulfonylhydrazone compounds: Synthesis, physical properties and inhibition studies against carbonic anhydrase II (CAII) enzyme [J].
Ozdemir, Ummuhan Ozmen ;
Altuntas, Aysegul ;
Gunduzalp, Ayla Balaban ;
Arslan, Fatma ;
Hamurcu, Fatma .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 128 :452-460
[35]   The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes [J].
Oktay, Koray ;
Kose, Leyla Polat ;
Sendil, Kivilcim ;
Gultekin, Mehmet Serdar ;
Gulcin, Ilhami ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2016, 31 (06) :939-945
[36]   Solid-phase synthesis of protonated nitrogen-containing heterocyclic compounds with the boron cluster anions starting from [Eu(H2O)9]2[B10Cl10]3: Synthesis, structure, and thermal properties of (HL)2[B10Cl10] (L=7-amino-4-methylcoumarin or 1-ethyl-2-(4-methoxyphenyl) azobenzimidazole) [J].
Malinina, Elena A. ;
Korolenko, Svetlana E. ;
Kubasov, Alexey S. ;
Buzanov, Grigorii A. ;
Golubev, Alexey, V ;
Goeva, Lyudmila, V ;
Simonenko, Nikolay P. ;
Avdeeva, Varvara V. ;
Kuznetsov, Nikolay T. .
JOURNAL OF SOLID STATE CHEMISTRY, 2021, 302