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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Efficient Synthesis of 2-[(3,4-Dichlorophenyl)methyl]-1H-benzimidazole Derivatives, and their α-Glucosidase Inhibitory and Antioxidant Activities

Author(s): Emre Menteşe, Fatih Yılmaz* and Nimet Baltaş

Volume 17, Issue 10, 2020

Page: [806 - 814] Pages: 9

DOI: 10.2174/1570178617666200330130024

Price: $65

Abstract

In this work, some new 2-[(3,4-dichlorophenyl)methyl]-1H-benzimidazole derivatives containing different five-membered heterocycles like 1,3,4-oxadiazole, 1,3,4-triazole, and 1,3,4- thiadiazole moieties were designed and efficiently synthesized starting from 2-[(3,4-dichlorophenyl) methyl]-1H-benzimidazole. The products were screened for their in vitro antioxidant and α-glucosidase inhibitory activities. Among the synthesized compounds, some of them showed efficient α-glucosidase inhibition with IC50 values ranging between 16.05 ± 0.94 and 77.02 ± 1.12 μg/mL when they were compared with the standard α-glucosidase inhibitor acarbose having IC50 value 12.04 ± 0.68 μg/mL. The antioxidant activity of all products was screened by using various in vitro antioxidant assays, including CUPric Reducing Antioxidant Capacity (CUPRAC) and Ferric Reducing Antioxidant Power (FRAP) assays. Also, the radical scavenging activities of the products were assayed by using the ABTS method.

Keywords: α-Glucosidase, antioxidant activity, benzimidazole, enzyme inhibition, thiadiazole, triazole.

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[1]
Ahmad, R.; Hashim, H.M.; Noor, Z.M.; Ismail, N.H.; Salim, F.; Lajis, N.H.; Shaari, K. Res. J. Med. Plant, 2011, 5, 587-595.
[http://dx.doi.org/10.3923/rjmp.2011.630.649]
[2]
Salehi, P.; Asghari, B.; Esmaeili, M.A.; Dehghan, H.; Ghazi, I. J. Med. Plants Res., 2013, 7, 257-266.
[3]
Qaseem, A.; Humphrey, L.L.; Sweet, D.E.; Starkey, M.; Shekelle, P. Ann. Intern. Med., 2012, 156(3), 218-231.
[http://dx.doi.org/10.7326/0003-4819-156-3-201202070-00011] [PMID: 22312141]
[4]
Hosseinzadeh, N.; Seraj, S.; Bakhshi-Dezffoli, M.E.; Hasani, M.; Khoshneviszadeh, M.; Fallah-Bonekohal, S.; Abdollahi, M.; Foroumadi, A.; Shafiee, A. Iran. J. Pharm. Res., 2013, 12(2), 325-330.
[PMID: 24250607]
[5]
Ren, S.; Xu, D.; Pan, Z.; Gao, Y.; Jiang, Z.; Gao, Q. Food Chem., 2011, 127, 1760-1763.
[http://dx.doi.org/10.1016/j.foodchem.2011.02.054] [PMID: 23675073]
[6]
Menteşe, E.; Ülker, S.; Kahveci, B. Chem. Heterocycl. Compd., 2015, 50, 1671-1682.
[http://dx.doi.org/10.1007/s10593-015-1637-1]
[7]
Uttara, B.; Singh, A.V.; Zamboni, P.; Mahajan, R.T. Curr. Neuropharmacol., 2009, 7(1), 65-74.
[http://dx.doi.org/10.2174/157015909787602823] [PMID: 19721819]
[8]
Pham-Huy, L.A.; He, H.; Pham-Huy, C. Int. J. Biomed. Sci., 2008, 4(2), 89-96.
[9]
Fang, Y-Z.; Yang, S.; Wu, G. Nutrition, 2002, 18(10), 872-879.
[http://dx.doi.org/10.1016/S0899-9007(02)00916-4] [PMID: 12361782]
[10]
Güngör, T.; Fouquet, A.; Teulon, J.M.; Provost, D.; Cazes, M.; Cloarec, A. J. Med. Chem., 1992, 35(23), 4455-4463.
[http://dx.doi.org/10.1021/jm00101a024] [PMID: 1447745]
[11]
Desai, K.G.; Desai, K.R. Bioorg. Med. Chem., 2006, 14(24), 8271-8279.
[http://dx.doi.org/10.1016/j.bmc.2006.09.017] [PMID: 17035035]
[12]
Yadav, S.; Narasimhan, B.; Kaur, H. Anticancer. Agents Med. Chem., 2016, 16(11), 1403-1425.
[http://dx.doi.org/10.2174/1871520616666151103113412] [PMID: 26526461]
[13]
Mavrova, A.Ts.; Anichina, K.K.; Vuchev, D.I.; Tsenov, J.A.; Denkova, P.S.; Kondeva, M.S.; Micheva, M.K. Eur. J. Med. Chem., 2006, 41(12), 1412-1420.
[http://dx.doi.org/10.1016/j.ejmech.2006.07.005] [PMID: 16996654]
[14]
Diao, X.; Wang, Y.; Jiang, Y.; Ma, D. J. Org. Chem., 2009, 74(20), 7974-7977.
[http://dx.doi.org/10.1021/jo9017183] [PMID: 19775088]
[15]
Baraldi, P.G.; Bovero, A.; Fruttarolo, F.; Preti, D.; Tabrizi, M.A.; Pavani, M.G.; Romagnoli, R. Med. Res. Rev., 2004, 24(4), 475-528.
[http://dx.doi.org/10.1002/med.20000] [PMID: 15170593]
[16]
Menteşe, E.; Karaali, N.; Akyüz, G.; Yılmaz, F.; Ülker, S.; Kahveci, B. Chem. Heterocycl. Compd., 2016, 52, 1017-1024.
[http://dx.doi.org/10.1007/s10593-017-2002-3]
[17]
Menteşe, E.; Yılmaz, F.; Emirik, M.; Ülker, S.; Kahveci, B. Bioorg. Chem., 2018, 76, 478-486.
[http://dx.doi.org/10.1016/j.bioorg.2017.12.023] [PMID: 29306066]
[18]
Kahveci, B.; Yılmaz, F.; Menteşe, E.; Ülker, S. Chem. Heterocycl. Compd., 2015, 51, 447-456.
[http://dx.doi.org/10.1007/s10593-015-1714-5]
[19]
Yılmaz, F.; Menteşe, E.; Baltaş, N. Lett. Drug Des. Discov., 2017, 14, 201-208.
[http://dx.doi.org/10.2174/1570180813666160609082633]
[20]
Usta, A.; Yılmaz, F.; Kapucu, G.; Baltaş, N.; Menteşe, E. Lett. Org. Chem., 2015, 12, 227-232.
[http://dx.doi.org/10.2174/1570178612666150203233804]
[21]
Kim, T.; Yang, H.Y.; Park, B.G.; Jung, S.Y.; Park, J-H.; Park, K.D.; Min, S-J.; Tae, J.; Yang, H.; Cho, S.; Cho, S.J.; Song, H.; Mook-Jung, I.; Lee, J.; Pae, A.N. Eur. J. Med. Chem., 2017, 125, 1172-1192.
[http://dx.doi.org/10.1016/j.ejmech.2016.11.017] [PMID: 27855359]
[22]
Kahveci, B.; Menteşe, E.; Özil, M.; Yılmaz, F.; Serdar, M. J. Heterocycl. Chem., 2016, 53, 975-980.
[http://dx.doi.org/10.1002/jhet.2107]
[23]
Menteşe, E.; Yılmaz, F.; Baltaş, N.; Bekircan, O.; Kahveci, B. J. Enzyme Inhib. Med. Chem., 2015, 30(3), 435-441.
[http://dx.doi.org/10.3109/14756366.2014.943203] [PMID: 25198894]
[24]
Ünver, Y.; Sancak, K.; Çelik, F.; Birinci, E.; Küçük, M.; Soylu, S.; Burnaz, N.A. Eur. J. Med. Chem., 2014, 84, 639-650.
[http://dx.doi.org/10.1016/j.ejmech.2014.01.014] [PMID: 25063946]
[25]
Boggu, P.; Venkateswararao, E.; Manickam, M.; Kwak, D.; Kim, Y.; Jung, S-H. Bioorg. Med. Chem., 2016, 24(8), 1872-1878.
[http://dx.doi.org/10.1016/j.bmc.2016.03.012] [PMID: 26976506]
[26]
Apak, R.; Güçlü, K.; Ozyürek, M.; Karademir, S.E. J. Agric. Food Chem., 2004, 52(26), 7970-7981.
[http://dx.doi.org/10.1021/jf048741x] [PMID: 15612784]
[27]
Benzie, I.F.F.; Strain, J.J. Methods Enzymol., 1999, 299, 15-27.
[http://dx.doi.org/10.1016/S0076-6879(99)99005-5] [PMID: 9916193]
[28]
Can, Z.; Baltas, N. Curr. Enzym. Inhib., 2016, 12, 188-194.
[http://dx.doi.org/10.2174/1573408012666160402001925]
[29]
Özil, M.; Emirik, M.; Beldüz, A.; Ülker, S. Bioorg. Med. Chem., 2016, 24(21), 5103-5114.
[http://dx.doi.org/10.1016/j.bmc.2016.08.024] [PMID: 27576293 ]

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