Synthesis and Molecular Docking studies of Some Tetrahydroimidazo[1,2-a] pyridine Derivatives as Potent α-Glucosidase Inhibitors

Subject Areas : Polymer

Mohammad R.  Asghariganjeh ¹ (Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran. Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran)
Ali A.  Mohammadi ² (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran. Chemistry and Chemical Engineering Research Center of Iran (CCERCI), 14335-186, Tehran, Iran.)
Elham  Tahanpesar ³ (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran)
Ayeh  Rayatzadeh ⁴ (Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran)
Somayeh  Makarem ⁵ (Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran)

Received: 2020-12-02 Accepted : 2020-12-02 Published : 2021-01-01

Keywords:

Abstract :

KAl(SO4)2.12H2O is found to efficiently and heterogeneously catalyze the one-pot three-component reaction of 2-(nitromethylene)imidazolidine, malononitrile and aldehydes under mild conditions to afford the corresponding tetrahydroimidazo[1,2-a]pyridine in good yields and short reaction times. Docking study of some compounds in the active site of α-glucosidase demonstrated that these compounds interacted with important active site residues with low binding energy in comparison to standard inhibitor acarbose.

References:

[1]. M.A. Martinez-Urbina, A. Zentella, M.A. Vilchis-Reyes, A. Guzman, O. Vargas, M.T.
Ramirez Apan, J.L. Ventura Gallegos, E. Diaz, Eur. J. Med. Chem., 45, 1211 (2010).
[2]. S. Mavel, J.L. Renou, C. Galtier, H. Allouchi, R. Snoeck, G. Andrei, E. De Clercq, J.
Balzarini, A. Gueiffier, Bioorg. Med. Chem., 10, 941 (2002).
[3]. J.J. Kaminski, A. Doweyko, J. Med. Chem., 40, 427 (1997).
[4]. A.K. Saxena, K.J. Schaper, QSAR Comb. Sci., 25, 590 (2006).

[5]. M. Bollini, J.J. Casal, D. E. Alvarez, L. Boiani, M. Gonzalez, H. Cerecetto, A.M. Bruno,
Bioorg. Med. Chem., 17, 1437 (2009).
[6]. M.H. Wiegand, Drugs, 68, 2411 (2008).
[7]. K.C. Rupert, J.R. Henry, J.H. Dodd, S.A. Wadsworth, D.E. Cavender, G.C. Olini, B.
Fahmy, J.J. Siekierka, Bioorg. Med. Chem. Lett., 13, 347 (2003).
[8]. Y. Rival, G. Grassy, G. Michel, Chem Pharm Bull., 40, 1170 (1992).
[9]. A. Chaouni-Benabdallah, C. Galtier, H. Allouchi, A. Kherbeche, J.C. Debouzy, J.C.
Teulade, O. Chavignon, M. Witvrouw, C. Pannecouque, J. Balzarini, E. De Clercq, C. Enguehard,
A. Gueiffier, Arch. Pharm., 334, 224 (2001).
[10]. S.Z. Langer, S. Arbilla, J. Benavides, B. Scatton, Adv. Biochem. Psychopharmacol., 46, 61
(1990).
[11]. T. Ueda, K. Mizushige, K. Yukiiri, T. Takahashi, M. Kohno, Cerebrovasc. Dis. , 16, 396
(2003).
[12]. T. Swainston Harrison, G.M. Keating, CNS Drugs., 19, 65 (2005).
[13]. P. Budumuru, S. Golagani, V.S.S. Kantamreddi, Asian J. Pharm. Clin. Res., 11, 252 (2018).
[14]. W. An, W. Wang, T. Yu, Y. Zhang, Z. Miao, T. Meng, J. Shen, Eur. J. Med. Chem., 112,
367 (2016).
[15]. R. Garamvolgyi, J. Dobos, A. Sipos, S. Boros, E. Illyes, F. Baska, L. Kekesi, I. Szabadkai,
C. Szantai-Kis, G. Keri, L. Orfi, Eur. J. Med. Chem., 108, 623 (2016).
[16]. Y.H. Fan, W. Li, D.D. Liu, M.X. Bai, H.R. Song, Y.N. Xu, S. Lee, Z.P. Zhou, J. Wang,
H.W. Ding, Eur. J. Med. Chem., 139, 95 (2017).
[17]. E. Allahabadi, S. Ebrahimi, M. Soheilizad, M. Khoshneviszadeh, M. Mahdavi,
TetrahedronLett., 58, 121 (2017).
[18]. N. Devi, D. Singh, G. Kaur, S. Mor, V.P.R.K. Putta, S. Polina, C.C. Malakar, V. Singh,
New. J. Chem., 41, 1082 (2017).
[19]. Z. Cui, B. Zhu, X. Li, H. Cao, Org. Chem. Front., 5, 2219 (2018).
[20]. J.E. Reynoso Lara, H. Salgado-Zamora, M.A. Bazin, M.E. Campos-Aldrete, P.J Marchand,
Heterocycl. Chem., 55, 1101 (2018).
[21]. M. Hammouda, Z.M. Abou Zeid, M.A. Metwally, Chem. Heterocycl. Comp., 41, 1525
(2005).
[22]. A. Alizadeh, T. Firuzyar, A. Mikaeili, J. Heterocycl. Chem., 50, 676 (2013).
[23]. A. Domling, Chem. Rev., 17, 106 (2006).
[24]. A.R. Karimi, F. Sedaghatpour, Synthesis, 51, 1731 (2010).
[25]. A. Alizadeh, N. Zohreh, Synlett., 3, 428 (2012).

[26]. R. Wang, Z.Q. Liu, J. Org. Chem., 78, 8696 (2013).
[27]. I. Yavari, R. Pashazadeh, R. Hosseinpour, E. Ghanbari, Tetrahedron Lett., 54, 2785 (2013).
[28]. R. Akbarzadeh, T. Amanpour, A. Bazgir, Tetrahedron, 70, 8142 (2014).
[29]. H. Kashtoh, M.T. Muhammad, J.J. Khan, S. Rasheed, A. Khan, S. Perveen, K. Javaid, K.M.
Khan, M.I. Choudhary, Bioorg. Chem., 65, 61 (2016).
[30]. M. Adib, F. Peytam, M.R. Jazi, M.M. Khanaposhtani, S. Mahernia, H.R. Bijanzadeh, M.
Jahani, S. Imanparast, M.A. Faramarzi, M. Mahdavi, B. Larijani, New J. Chem., 42, 17268 (2018).
[31]. J.Azizian, A.A. Mohammadi, A.R. Karimi, M.R. Mohammadizadeh, J. Org. Chem., 70, 350
(2005).
[32]. A.A. Mohammadi, S. Taheri, A. Amini, R. Ahdenov, Mol. Divers., 22, 999 (2018).
[33]. A.A. Mohammadi, S. Taheri, A. Amouzegar, R. Ahdenov, M.R. Halvagar, A.S. Sadr, J. Mol.
Struct., 1139, 166 (2017).
[34]. A.A. Mohammadi, S. Makarem, R. Ahdenov, N.A. Notash, Mol. Divers., Article in Press
(2019). DOI: 10.1007/s11030-019-09979-8
[35]. A.A. Mohammadi, S. Taheri, S. Askari, J. Heterocycl. Chem., 54, 484 (2017).
[36]. A.A.Mohammadi, S. Taheri, A. Amouzegar, J. Heterocycl. Chem., 54, 2085 (2017).
[37]. A.A. Mohammadi, S. Taheri, S. Askari, R. Ahdenov, J. Heterocycl. Chem., 52, 1871 (2015).
[38]. M. Adib, F. Peytam, M.R. Jazi, S. Mahernia, H.R. Bijanzadeh, M. Jahani, M.M.
Khanaposhtani, S. Imanparast, M.A. Faramarzi, M. Mahdavi, B. Larijani, Eur. J. Med. Chem., 155,
353 (2018).