Synthesis of Benzimidazole-sugar Derivatives: a Potential Treatment for Alzheimer’s Disease

Authors

  • Seda YUKSEKDANACI Department of Occupational Health and Safety, Faculty of Health Sciences, Uşak University, Uşak, Turkey. Email: seda.yuksekdanaci@usak.edu.tr. https://orcid.org/0000-0003-0387-8591
  • Demet ASTLEY Department of Chemistry, Faculty of Science, Ege University, Izmir, Turkey. Corresponding author: seda.yuksekdanaci@usak.edu.tr. https://orcid.org/0000-0001-7436-9407
  • Murat SENTURK Department of Biochemistry, Faculty of Pharmacy, Ağrı İbrahim Çeçen University, Ağrı, Turkey. Corresponding author: seda.yuksekdanaci@usak.edu.tr.

DOI:

https://doi.org/10.24193/subbchem.2023.4.08

Keywords:

Benzimidazole; amino acid; glycosyl thiourea; carbonic anhydrase; cholinesterase

Abstract

In this study, a new series of chiral benzimidazole-glycosyl thiourea derivatives (5-10) were synthesized and evaluated for their inhibitory effects against hCA I, hCA II, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The structures of the benzimidazole-glycosyl thiourea compounds were determined by FTIR, 1H-NMR, 13C-NMR and elemental analysis. The KI values for the CA isoenzymes of the synthesized materials ranged from 6.03 to 42.98 nM. KI values for cholinesterase enzymes were shown to be between 5.32 and 39.14 nM. It was observed that compound 10 is the best hCA I inhibitor (KI:6.03 nM), compund 9 is the best hCAII inhibitor (KI:17.29 nM) and compound 8 is the best AChE (KI:5.32 nM) and the best BChE (KI:18.73 nM) inhibitor.

References

J. D. Ulrich; D. M. Holtzman; ACS Chem. Neurosci.; 2016; 7; 420-427.

L. S. Schneider; Clinics in Geriatric Medicine; 2001; 17; 337-358.

A. V. Terry; J. J. Buccafusco; J Pharmacol Exp. Ther.; 2003; 306; 821-827.

M. R. Picciotto; M. J. Higley; Y. S. Mineur; Neuron; 2012; 76; 116-129;

P. Bar-On; C. B. Millard; M. Harel; H. Dvir; A. Enz; L. Sussman; I. Silman; Biochemistry; 2002; 41; 3555-3564.

F. Comert Onder; K. Sahin; M. Senturk; S. Durdagi; M. Ay; J. Mol. Graph. Modell; 2022; 115; 108210.

M. Ozil; H. T. Balaydin; M. Senturk; Bioorganic Chemistry; 2019; 86; 705-713.

R. Cakmak; E. Basaran; M. Senturk; Arch. Pharm.; 2022; 355; e2100430.

C. T. Supuran; Nat. Rev. Drug Discov.; 2008; 7; 168-181.

M. Hilvo; L. Baranauskiene; A. M. Salzano; A. Scaloni; D. Matulis; A. Innocenti; A. Scozzafava; S. M. Monti; A. Di Fiore; G. De Simone; J. Biol. Chem.; 2008; 283; 27799-27809.

G. Provensi; F. Carta; A. Nocentini; C. T. Supuran; F. Casamenti; M. B. Passani; S. Fossati; Int. J Mol. Sci.; 2019; 20; 4724.

S. Isik; D. Vullo; S. Durdagi; D. Ekinci; M. Senturk; A. Cetin; E. Senturk; C. T. Supuran; Bioorg. Med. Chem. Lett.; 2015; 25; 5636-5641.

T. Arslan; Z. Biyiklioglu; M. Senturk; RSC Adv.; 2018; 8; 10172-10178.

R. Yaseen; D. Ekinci; M. Senturk; A. D. Hameed; S. Ovais; P. Rathore; M. Samim; K. Javed; C. T. Supuran; Bioorg. Med. Chem. Lett.; 2016; 26; 1337-1341.

H. T. Balaydın; M. Senturk; A. Menzek; Bioorg. Med. Chem. Lett.; 2012; 22; 1352-1357.

I. Fidan; R. E. Salmas; M. Arslan; M. Senturk; S. Durdagi; D. Ekinci; E. Senturk; E. Cosgun; C. T. Supuran; Bioorganic & Medicinal Chemistry; 2015; 23; 7353-7358.

M. Guney; H. Cavdar; M. Senturk; D. Ekinci; Bioorganic & Medicinal Chemistry Letters; 2015; 25; 3261-3263.

S. Durdagi; N. Korkmaz; S. Işık; D. Vullo; D. Astley; D. Ekinci; R. E. Salmas; M. Senturk; C. T. Supuran; Journal of Enzyme Inhibition and Medicinal Chemistry; 2016; 31; 1214-1220.

D. A. Butterfield; T. Reed; S. F. Newman; R. Sultana; Free Radic. Biol. Med.; 2007; 43; 658-677.

R. Sultana; D. Boyd-Kimball; J. Cai; W. M. Pierce; J. B. Klein; M. Merchant; D. A. Butterfield; J. Alzheimers Dis.; 2017; 11; 156-164.

W. Meier-Ruge; P. Iwangoff; K. Reichlmeier; Arch. Gerontol. Geriatr.; 1984; 3; 161-165.

E. Drummond; S. Nayak; A. Faustin; G. Pires; R. A. Hickman; M. Askenazi; M. Cohen; T. Haldiman; C. Kim; X. Han; Acta Neuropathol.; 2017; 133; 933-954.

A. Pollard; F. Shephard; J. Freed; S. Liddell; L. Chakrabarti; Aging; 2016; 8; 2425-2436.

B. G. Jang; S. M. Yun; K. Ahn; J. H. Song; S. A. Jo; Y. Y. Kim; D. K. Kim; M. H. Park; C. Han; Y. H. Koh; J. Alzheimers Dis.; 2010; 21; 939-945.

F. Angiulli; M. E. Solesio; L. Debure; J. R. Cejudo; T. Wisniewski; S. Fossati; Alzheimer’s &Dement; 2018; 14; 1296.

F. Fei; Z. Zhou; Expert Opin. Ther. Pat.; 2013; 23; 1157-1179.

Y. N. Wang; R. R. Y. Bheemanaboina; G. X. Cai; C. H. Zhou; Inorg. Med. Chem. Lett.; 2018; 28; 1621-1628.

Z. Wang; X. Deng; S. Xiong; R. Xiong; J. Liu; L. Zou; Nat. Product. Res.; 2017; 32; 2900-2909.

G. R. Morais; E. Palma; F. Marques; L. Gano; M. C. Oliveira; A. Abrunhosa; J. Heterocyclic Chem.; 2017; 54; 255-267.

Y. Bansal; O. Silakari; Bioorg. Med. Chem.; 2012; 20; 6208-6236.

R. S. Keri; A. Hiremathad; S. Budagumpi; B. M. Nagaraja; Chem. Biol. Drug Des.; 2015; 86; 19-65.

Y. Fang; H. Zhou; Q. Gu; J. Xu; Eur. J of Med. Chem.; 2019; 167; 133-145.

G. Sarıkaya; G. Çoban; S. Parlar; A. H. Tarikogullari; G. Armagan, M. A. Erdoğan; V. Alptüzün; A. S. Alpan; Arch Pharm Chem Life Sci.; 2018; 351; 1800076-1800093.

L. Dinparast; G. Zengin; M. B. Bahadori; Biointerface Research in Applied Chemistry; 2021; 11; 10739-10745.

T. Kim; H. Y. Yang; B. G. Park; S. Y. Jung; J. Park; K. D. Park; S. J. Min; J. Tae; H. Yang; S. Cho; S. J. Cho; H. Song; I. Mook-Jung; J. Lee; A. N. Pae; Eur. J of Med. Chem.; 2017; 125; 1172-1192.

A. B. Reitz; R. W. Tuman; C. S. Marchione; A. D. Jordan; C. R. Jr Bowden; B. E. Maryanoff; J. Med. Chem.; 1989; 32; 2110-2116.

H. Parrot-Lopez; H. Galons; A. W. Coleman; J. Mahnteau; M. Miocque; Tetrahedron Lett.; 1992; 33; 209-212.

A. S. Dandale; D. V. Mangte; S. P. Deshmukh; The 14th International Electronic Conference on Synthetic Organic Chemistry; 2010.

Y. Wu; S. Ren; L. Wang; Y. Wang; S. Liu; W. Liu; D. Shi; Z. Cao; Journal of Chemical Research; 2020; 44; 363-366.

L. Yin; F. Cheng; Q. Li; W. Liu; X. Liu; Z. Cao; S. Shi; Journal of Chemical Research; 2016; 40; 545-548.

L. Cao; K. Jiang; Z. Shao; Y. Wang; S. Liu; X. Lu; Y. Wu; C. Chen; Z. Su; L. Wang; W. Liu; D. Shi; Z. Cao; Russian J of Org. Chem.; 2021; 57; 1513-1518.

D. Shendage; R. Fröhlich; G. Haufe; Org. Lett.; 2004; 6; 3675-3678.

N. Korkmaz; O. A. Obaidi; M. Senturk; D. Astley; D. Ekinci; C. T. Supuran; Journal of Enzyme Inhibition and Medicinal Chemistry; 2015; 30; 75-80.

M. L. Wolfrom; Methods in carbohydrate Chemistry. London: Academic; New York; San Francisco; 1963.

F. Weygard; H. Ziemann; H. J. Bestmann; Chem. Ber.; 1958; 91; 2534-2537.

Z. Shusheng; Z. Tianrong; C. Kun; X. Youfeng; Y. Bo; Eur. J. Med. Chem.; 2008; 43; 2778-2783.

T. L. Rosenberry; X. Brazzolotto; I. R. Macdonald; M. Wandhammer; M. Trovaslet-Leroy; S. Darvesh; F. Nachon; Molecules; 2017; 22; 2098-2119.

V. M. Krishnamurthy; G. K. Kaufman; A. R. Urbach; I. Gitlin; K. L. Gudiksen; D. B. Weibel; G. M. Whitesides; Chem. Rev.; 2008; 108; 946–1051.

C. A. Lesburg; C. Huang; D. W. Christianson; C. A. Fierke; Biochemistry; 1997; 36; 15780–15791.

T. Arslan; M. B. Ceylan; H. Baş; Z. Biyiklioglu; M. Senturk; Dalton Transactions; 2020; 49; 203-209.

J. M. G. Fernandez; C. O. Mellet; Advances in Carbohydrate Chemistry and Biochemistry; 2000; 55; 35-135.

L. J. Haynes; F. H. Newth; Advances in Carbohydrate Chemistry; 1995; 10; 207-256.

H. Osborn; Carbohydrates; 1st ed.; Academic Press; United Kingdom; 2003.

G. L. Ellman; K. D. Courtney; V. Jr Andres; R. M. Featherstone; Biochem. Pharmacol.; 1961; 7; 91-95.

J. A. Verpoorte; S. Mehta; J. T. Edsall; J. Biol. Chem.; 1967; 242; 4221-4229.

K. Zilbeyaz; N. Stellenboom; M. Guney; A. Oztekin; M. Senturk M; J Biochem. Mol. Toxicol.; 2018; 32; e22210.

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Published

2023-12-20

How to Cite

YUKSEKDANACI, S. ., ASTLEY, D. ., & SENTURK, M. . (2023). Synthesis of Benzimidazole-sugar Derivatives: a Potential Treatment for Alzheimer’s Disease. Studia Universitatis Babeș-Bolyai Chemia, 68(4), 111–126. https://doi.org/10.24193/subbchem.2023.4.08

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