Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis of New Glucose-containing 5-Arylisoxazoles and their Enzyme Inhibitory Activity

Author(s): Roshanak Hariri, Aida Iraji, Somayeh Mojtabavi, Mina Saeedi, Mohammad Ali Faramarzi, Mohsen Amini and Tahmineh Akbarzadeh*

Volume 21, Issue 8, 2024

Published on: 25 January, 2024

Page: [707 - 719] Pages: 13

DOI: 10.2174/0115701786283334231228104931

Price: $65

Abstract

Carbohydrates are an important group of biomolecules that have received special attention due to their significant role in the design and synthesis of new bioactive compounds. In this study, a new class of 5-arylisoxazole-glucose hybrids was designed and synthesized for evaluation of their inhibitory effects on α-glucosidase, α-amylase, and tyrosinase. The target compounds depicted selective α-glucosidase inhibitory activity over α-amylase, which is an important factor in reducing probable gastrointestinal problems in the treatment of type 2 diabetes. In this respect, compound 9a, possessing the phenylisoxazole group, was found to be the most potent α-glucosidase inhibitor (IC50 = 292.2 ± 0.1 μM) compared to acarbose (IC50 = 750.2 ± 0.1 μM) as the positive control. All compounds were also evaluated for their anti-tyrosinase effect, and among them, compound 9j, containing a fluoroaryl moiety, showed potent activity (IC50 = 50.1 ± 6.3 μM) in comparison to kojic acid (IC50 = 23.6 ± 2.6 μM). Also, docking studies were performed to investigate the probable mode of action, which indicated the construction of important H-bonding interactions between the sugar moiety and the enzyme’s active sites. According to the results, hybrids containing heterocycles attached to glucose can be used to inhibit α-glucosidase.

« Previous Next »
Graphical Abstract

[1]
Jiang, H.; Qin, X.; Wang, Q.; Xu, Q.; Wang, J.; Wu, Y.; Chen, W.; Wang, C.; Zhang, T.; Xing, D.; Zhang, R. Eur. J. Med. Chem., 2021, 223, 113633.
[http://dx.doi.org/10.1016/j.ejmech.2021.113633] [PMID: 34171659]
[2]
Cummings, R.D. Glycoconj. J., 2019, 36(4), 241-257.
[http://dx.doi.org/10.1007/s10719-019-09876-0] [PMID: 31267247]
[3]
Pan, L.; Cai, C.; Liu, C.; Liu, D.; Li, G.; Linhardt, R.J.; Yu, G. Curr. Opin. Biotechnol., 2021, 69, 191-198.
[http://dx.doi.org/10.1016/j.copbio.2020.12.023] [PMID: 33530023]
[4]
Lopes, J.P.B.; Silva, L.; Lüdtke, D.S. RSC. Medicinal Chemistry, 2021, 12(12), 2001-2015.
[http://dx.doi.org/10.1039/D1MD00217A] [PMID: 35028560]
[5]
Kassem, A.F.; Nassar, I.F.; Abdel-Aal, M.T.; Awad, H.M.; El-Sayed, W.A. Chem. Pharm. Bull., 2019, 67(8), 888-895.
[http://dx.doi.org/10.1248/cpb.c19-00280] [PMID: 31366838]
[6]
Tolan, H.E.M.; El-Sayed, W.A.; Tawfek, N.; Abdel-Megeid, F.M.E.; Kutkat, O.M. Nucleosides Nucleotides Nucleic Acids, 2020, 39(5), 649-670.
[http://dx.doi.org/10.1080/15257770.2019.1674331] [PMID: 31599202]
[7]
Toobaei, Z.; Yousefi, R.; Panahi, F.; Shahidpour, S.; Nourisefat, M.; Doroodmand, M.M.; Khalafi-Nezhad, A. Carbohydr. Res., 2015, 411, 22-32.
[http://dx.doi.org/10.1016/j.carres.2015.04.005] [PMID: 25957572]
[8]
Khajeh Dangolani, S.; Panahi, F.; Tavaf, Z.; Nourisefat, M.; Yousefi, R.; Khalafi-Nezhad, A. ACS Omega, 2018, 3(8), 10341-10350.
[http://dx.doi.org/10.1021/acsomega.8b01124] [PMID: 31459162]
[9]
Hudson, K.L.; Bartlett, G.J.; Diehl, R.C.; Agirre, J.; Gallagher, T.; Kiessling, L.L.; Woolfson, D.N. J. Am. Chem. Soc., 2015, 137(48), 15152-15160.
[http://dx.doi.org/10.1021/jacs.5b08424] [PMID: 26561965]
[10]
Drinnan, N.; Vari, F. Mini Rev. Med. Chem., 2003, 3(7), 633-649.
[http://dx.doi.org/10.2174/1389557033487737] [PMID: 14529505]
[11]
Oraii, A.; Shafiee, A.; Jalali, A.; Alaeddini, F.; Saadat, S.; Masoudkabir, F.; Vasheghani-Farahani, A.; Heidari, A.; Sadeghian, S.; Boroumand, M.; Karimi, A.; Franco, H. O. BMC Endocr. Disord., 2022, 22(1), 248.
[http://dx.doi.org/10.1186/s12902-022-01161-w] [PMID: 36253738]
[12]
Saeedi, M.; Raeisi-Nafchi, M.; Sobhani, S.; Mirfazli, S.S.; Zardkanlou, M.; Mojtabavi, S.; Faramarzi, M.A.; Akbarzadeh, T. Mol. Divers., 2021, 25(4), 2399-2409.
[http://dx.doi.org/10.1007/s11030-020-10137-8] [PMID: 33047276]
[13]
Iraji, A.; Saeedi, M.; Rafiee-Sereshky, T.; Mojtabavi, S.; Faramarzi, M.A.; Akbarzadeh, T. Lett. Org. Chem., 2022, 19(12), 1084-1093.
[http://dx.doi.org/10.2174/1570178619666220401143634]
[14]
Saeedi, M.; Eslami, A.; Mirfazli, S.S.; Zardkanlou, M.; Faramarzi, M.A.; Mahdavi, M.; Akbarzadeh, T. Lett. Drug Des. Discov., 2021, 18(5), 436-444.
[http://dx.doi.org/10.2174/1570180817999201104125018]
[15]
Farid, S.M.; Iraji, A.; Mojtabavi, S.; Ghasemi, M.; Faramarzi, M.A.; Mahdavi, M. Quinazolinone-1, 2, 3-triazole-acetamide conjugates as potent α-glucosidase inhibitors: Synthesis, enzyme inhibition, kinetic analysis, and molecular docking study; RSC Medicinal Chemistry, 2023.
[16]
Iraji, A.; Shareghi-Brojeni, D.; Mojtabavi, S.; Faramarzi, M.A.; Akbarzadeh, T.; Saeedi, M. Sci. Rep., 2022, 12(1), 8647.
[http://dx.doi.org/10.1038/s41598-022-11771-y] [PMID: 35606520]
[17]
Saeedi, M.; Mohammadi-Khanaposhtani, M.; Asgari, M.S.; Eghbalnejad, N.; Imanparast, S.; Faramarzi, M.A.; Larijani, B.; Mahdavi, M.; Akbarzadeh, T. Bioorg. Med. Chem., 2019, 27(23), 115148.
[http://dx.doi.org/10.1016/j.bmc.2019.115148] [PMID: 31679980]
[18]
Kageyama, S. Varieties and characteristics of drugs for diabetes. How to Choose and Use Drugs for Diabetes Tokyo; Nankaido: Japan, 1996, pp. 23-44.
[19]
Qian, W.; Liu, W.; Zhu, D.; Cao, Y.; Tang, A.; Gong, G.; Su, H. Exp. Ther. Med., 2020, 20(1), 173-185.
[http://dx.doi.org/10.3892/etm.2020.8687] [PMID: 32509007]
[20]
Hariri, R.; Saeedi, M.; Akbarzadeh, T. J. Pept. Sci., 2021, 27(7), e3329.
[http://dx.doi.org/10.1002/psc.3329] [PMID: 33860571]
[21]
Pillaiyar, T.; Namasivayam, V.; Manickam, M.; Jung, S.H. J. Med. Chem., 2018, 61(17), 7395-7418.
[http://dx.doi.org/10.1021/acs.jmedchem.7b00967] [PMID: 29763564]
[22]
Agrawal, N.; Mishra, P. Med. Chem. Res., 2018, 27(5), 1309-1344.
[http://dx.doi.org/10.1007/s00044-018-2152-6] [PMID: 32214770]
[23]
Walunj, Y.; Mhaske, P.; Kulkarni, P. Mini Rev. Org. Chem., 2021, 18(1), 55-77.
[http://dx.doi.org/10.2174/1570193X17999200511131621]
[24]
Pandhurnekar, C.P.; Pandhurnekar, H.C.; Mungole, A.J.; Butoliya, S.S.; Yadao, B.G. J. Heterocycl. Chem., 2023, 60(4), 537-565.
[http://dx.doi.org/10.1002/jhet.4586]
[25]
Gujjarappa, R.; Sravani, S.; Kabi, A.K.; Garg, A.; Vodnala, N.; Tyagi, U. Nanostruct. Biomat: Basic Struct. Appl., 2022, 379-400.
[26]
Saeedi, M.; Mohtadi-Haghighi, D.; Mirfazli, S.S.; Mahdavi, M.; Hariri, R.; Lotfian, H.; Edraki, N.; Iraji, A.; Firuzi, O.; Akbarzadeh, T. Chem. Biodivers., 2019, 16(2), e1800433.
[http://dx.doi.org/10.1002/cbdv.201800433] [PMID: 30460743]
[27]
Saeedi, M.; Rastegari, A.; Hariri, R.; Mirfazli, S.S.; Mahdavi, M.; Edraki, N.; Firuzi, O.; Akbarzadeh, T. Chem. Biodivers., 2020, 17(5), e1900746.
[http://dx.doi.org/10.1002/cbdv.201900746] [PMID: 32154628]
[28]
Najafi, Z.; Mahdavi, M.; Saeedi, M.; Sabourian, R.; Khanavi, M.; Safavi, M.; Tehrani, M.; Shafiee, A.; Foroumadi, A.; Akbarzadeh, T. Lett. Drug Des. Discov., 2016, 14(1), 58-65.
[http://dx.doi.org/10.2174/1570180813666160628085515]
[29]
Vafadarnejad, F.; Karimpour-Razkenari, E.; Sameem, B.; Saeedi, M.; Firuzi, O.; Edraki, N.; Mahdavi, M.; Akbarzadeh, T. Bioorg. Chem., 2019, 92, 103192.
[http://dx.doi.org/10.1016/j.bioorg.2019.103192] [PMID: 31446239]
[30]
Shareghi-Boroujeni, D.; Iraji, A.; Mojtabavi, S.; Faramarzi, M.A.; Akbarzadeh, T.; Saeedi, M. Bioorg. Chem., 2021, 111, 104869.
[http://dx.doi.org/10.1016/j.bioorg.2021.104869] [PMID: 33839583]
[31]
Rastegari, A.; Safavi, M.; Vafadarnejad, F.; Najafi, Z.; Hariri, R.; Bukhari, S.N.A.; Iraji, A.; Edraki, N.; Firuzi, O.; Saeedi, M.; Mahdavi, M.; Akbarzadeh, T. Mol. Divers., 2022, 26(1), 409-428.
[http://dx.doi.org/10.1007/s11030-021-10248-w] [PMID: 34273065]
[32]
Saeedi, M.; Hashemi, M.; Mahdavi, M.; Rafinejad, A.; Najafi, Z.; Mirfazli, S.S. Polycycl. Aromat. Compd.,; , 2019.
[33]
Saidi, I.; Manachou, M.; Znati, M.; Bouajila, J.; Ben Jannet, H. J. Mol. Struct., 2022, 1247, 131379.
[http://dx.doi.org/10.1016/j.molstruc.2021.131379]
[34]
Olanipekun, B.E.; Ponnapalli, M.G.; Patel, H.K.; Munipalle, K.; Shaik, K. Nat. Prod. Res., 2021, 1-6.
[PMID: 34625004]
[35]
Gupta, S.J.; Dutta, S.; Gajbhiye, R.L.; Jaisankar, P.; Sen, A.K. Bioorg. Chem., 2017, 72, 11-20.
[http://dx.doi.org/10.1016/j.bioorg.2017.03.006] [PMID: 28346871]
[36]
Zhang, Y.; Gao, H.; Liu, R.; Liu, J.; Chen, L.; Li, X.; Zhao, L.; Wang, W.; Li, B. Bioorg. Med. Chem. Lett., 2017, 27(18), 4309-4313.
[http://dx.doi.org/10.1016/j.bmcl.2017.08.035] [PMID: 28838691]
[37]
Ershov, A.Y.; Martynenkov, A.A.; Lagoda, I.V.; Yakimansky, A.V. Russ. J. Gen. Chem., 2019, 89(2), 292-299.
[http://dx.doi.org/10.1134/S1070363219020208]
[38]
Ali, A.; Cottrell, J.J.; Dunshea, F.R. Antioxidants, 2023, 12(2), 254.
[http://dx.doi.org/10.3390/antiox12020254] [PMID: 36829816]
[39]
Adinortey, C.A.; Kwarko, G.B.; Koranteng, R.; Boison, D.; Obuaba, I.; Wilson, M.D.; Kwofie, S.K. Curr. Issues Mol. Biol., 2022, 44(2), 963-987.
[http://dx.doi.org/10.3390/cimb44020064] [PMID: 35723349]
[40]
Ali, A.; Cottrell, J.J.; Dunshea, F.R. Food Res. Int., 2022, 162(Pt B), 111951.
[http://dx.doi.org/10.1016/j.foodres.2022.111951] [PMID: 36461310]
[41]
Bishoff, H. Diabetes Res. Clin. Pract., 1985, 1, S53.
[42]
Filler, R.; Saha, R. Future Med. Chem., 2009, 1(5), 777-791.
[http://dx.doi.org/10.4155/fmc.09.65] [PMID: 21426080]
[43]
Purser, S.; Moore, P.R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev., 2008, 37(2), 320-330.
[http://dx.doi.org/10.1039/B610213C] [PMID: 18197348]
[44]
García P.; Salazar, M.O.; Ramallo, I.A.; Furlan, R.L.E. ACS Comb. Sci., 2016, 18(6), 283-286.
[http://dx.doi.org/10.1021/acscombsci.6b00004] [PMID: 27144399]
[45]
Chochkova, M.; Stoykova, B.; Ivanova, G.; Ranz, A.; Guo, X.; Lankmayr, E.; Milkova, T. J. Fluor. Chem., 2013, 156, 203-208.
[http://dx.doi.org/10.1016/j.jfluchem.2013.09.013]
[46]
Berkowitz, D.B.; Karukurichi, K.R.; de la Salud-Bea, R.; Nelson, D.L.; McCune, C.D. J. Fluor. Chem., 2008, 129(9), 731-742.
[http://dx.doi.org/10.1016/j.jfluchem.2008.05.016] [PMID: 19727327]
[47]
Sharma, A.K.; Srivastava, G.N.; Roy, A.; Sharma, V.K. Front. Pharmacol., 2017, 8, 880.
[http://dx.doi.org/10.3389/fphar.2017.00880] [PMID: 29249969]
[48]
Akbarzadeh, T.; Rafinejad, A.; Mollaghasem, J.M.; Safavi, M.; Fallah-Tafti, A.; Pordeli, M.; Ardestani, S.K.; Shafiee, A.; Foroumadi, A. Arch. Pharm., 2012, 345(5), 386-392.
[http://dx.doi.org/10.1002/ardp.201100345] [PMID: 22266847]
[49]
Abou-Seri, S.M.; Eissa, A.A.M.; Behery, M.G.M.; Omar, F.A. Bioorg. Chem., 2021, 116, 105334.
[http://dx.doi.org/10.1016/j.bioorg.2021.105334] [PMID: 34534755]
[50]
Khalifa, N.M.; Al-Omar, M.A.; Nossier, E.S. Russ. J. Gen. Chem., 2017, 87(12), 2909-2914.
[http://dx.doi.org/10.1134/S1070363217120301]
[51]
Asgari, M.S.; Mohammadi-Khanaposhtani, M.; Kiani, M.; Ranjbar, P.R.; Zabihi, E.; Pourbagher, R.; Rahimi, R.; Faramarzi, M.A.; Biglar, M.; Larijani, B.; Mahdavi, M.; Hamedifar, H.; Hajimiri, M.H. Bioorg. Chem., 2019, 92, 103206.
[http://dx.doi.org/10.1016/j.bioorg.2019.103206] [PMID: 31445191]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy