European Journal of Chemistry

Quinazolin derivatives as emerging alpha-glucosidase inhibitors

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Published: Dec 31, 2018
DOI: https://doi.org/10.5155/eurjchem.9.4.322-330.1748
Keywords:
Diabetes, Acarbose, Inhibitors, Inflammation, Alpha-glucosidase, Quninazoline derivatives
Section
Research Article
Issue
Vol. 9 No. 4 (2018): December 2018
Dates
Received 2018-05-29
Accepted 2018-09-06
Published 2018-12-31
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Main Article Content

Ashok Reddy Ankireddy
Department of Chemistry, Gitam University, Hyderabad, Rudraram Mandal, Sangareddy District, Patancheru, Hyderabad, Telangana 502329, India
http://orcid.org/0000-0001-9621-0907
Rambabu Gundla
Department of Chemistry, Gitam University, Hyderabad, Rudraram Mandal, Sangareddy District, Patancheru, Hyderabad, Telangana 502329, India
http://orcid.org/0000-0003-0390-6505
Tuniki Balaraju
Department of Chemistry, Birla Institute of Technology, Mesra, Jharkhand 835215, India
http://orcid.org/0000-0003-2466-1471
Venkanna Banothu
Centre for Biotechnology (CBT), Institute of Science & Technology (IST), Jawaharlal Nehru Technological University Hyderabad (JNTUH), Kukatpally, Hyderabad, Telangana State, 500085, India
http://orcid.org/0000-0002-4446-8786
Krishna Prasad Gundla
Department of Chemistry, Gitam University, Hyderabad, Rudraram Mandal, Sangareddy District, Patancheru, Hyderabad, Telangana 502329, India
http://orcid.org/0000-0002-2096-1664
Uma Addepally
Centre for Biotechnology (CBT), Institute of Science & Technology (IST), Jawaharlal Nehru Technological University Hyderabad (JNTUH), Kukatpally, Hyderabad, Telangana State, 500085, India
http://orcid.org/0000-0002-1074-1588
Jithendra Chimakurthy
Department of Pharmaceutical Sciences, Vignan’s Foundation for Science, Technology and Research Vadlamudi, Guntur, Andhra Pradesh 522213, India
http://orcid.org/0000-0002-2948-4948

Abstract

A series of C-7 substituted-2-morpholino-N-(pyridin-2-ylmethyl)quinazolin-4-amine have been synthesized and biochemical assay was examined against α-glucosidase function inhibition activity. A structure activity and structure property relationship study was experimented to surface the new hit compound. This study led to the identification of C-7substituted quinazolines with minimum inhibitory concentrations (MICs) in the preffered micromolar range in addition with interesting physicochemical properties. Biological evaluation yielded eight analogs which rose with significant α-glucosidase inhibition potency (IC50 values < 2 μM, where reference compound (Acarbose) potency value is IC50 = 0.586 uM) and could be promising candidates for further lead optimization.


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How to Cite
(1)
Ankireddy, A. R.; Gundla, R.; Balaraju, T.; Banothu, V.; Gundla, K. P.; Addepally, U.; Chimakurthy, J. Quinazolin Derivatives As Emerging Alpha-Glucosidase Inhibitors. Eur. J. Chem. 2018, 9, 322-330.

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References

[1]. Geiss, L. S.; Wang, J.; Cheng, Y. J.; Thompson, T. J.; Barker, L.; Li, Y.; Albright, A. L.; Gregg, E. W. Jama 2014, 312, 1218-1226.
https://doi.org/10.1001/jama.2014.11494

[2]. Ferreres, F.; Gil-Izquierdo, A.; Vinholes, J.; Silva, S. T.; Valentao, P.; Andrade, P. B. Food Chem. 2012, 134, 894-904.
https://doi.org/10.1016/j.foodchem.2012.02.201

[3]. Bruni, C.; Sica, V.; Auricchio, F.; Covelli, I. Biochim. Biophys. Acta (BBA)-Enzymol. 1970, 212, 470-477.

[4]. Garlapati, R.; Pottabathini, N.; Gurram, V.; Chaudhary, A. B.; Chunduri, V. R.; Patro, B. Tetrahedron Lett. 2012, 53, 5162-5166.
https://doi.org/10.1016/j.tetlet.2012.07.061

[5]. Garlapati, R.; Pottabathini, N.; Gurram, V.; Kasani, K. S.; Gundla, R.; Thulluri, C.; Machiraju, P. K.; Chaudhary, A. B.; Addepally, U.; Dayam, R. Org. Biomol. Chem. 2013, 11, 4778-4791.
https://doi.org/10.1039/c3ob40636a

[6]. Chandrika, P. M.; Yakaiah, T.; Rao, A. R. R.; Narsaiah, B.; Reddy, N. C.; Sridhar, V.; Rao, J. V. Eur. J. Med. Chem. 2008, 43, 846-852.
https://doi.org/10.1016/j.ejmech.2007.06.010

[7]. Ram, V. J.; Tripathi, B. K.; Srivastava, A. K. Bioorg. Med. Chem. 2003, 11, 2439-2444.
https://doi.org/10.1016/S0968-0896(03)00142-1

[8]. Koh, K. K.; Park, S. M.; Quon, M. J. Circulation 2008, 117, 3238-3249.
https://doi.org/10.1161/CIRCULATIONAHA.107.741645

[9]. Saltiel, A. R.; Olefsky, J. M. Diabetes 1996, 45, 1661-1669.
https://doi.org/10.2337/diab.45.12.1661

[10]. De Melo, E. B.; Gomes, A. S.; Carvalho, I. Tetrahedron 2006, 62, 10277-10302.
https://doi.org/10.1016/j.tet.2006.08.055

[11]. Landgraf, R. Drugs Aging 2000, 17, 411-425.
https://doi.org/10.2165/00002512-200017050-00007

[12]. Sinclair, A. J. International textbook of Diabetes mellitus, Wiley, Worcestershire, United Kingdom, 2004.

[13]. Wan, Z. K.; Wacharasindhu, S.; Levins, C. G.; Lin, M.; Tabei, K.; Mansour, T. S. J. Org. Chem. 2007, 72, 10194-10210.
https://doi.org/10.1021/jo7020373

[14]. Goto, S.; Tsuboi, H.; Kanoda, M.; Mukai, K.; Kagara, K. Org. Proc. Res. Dev. 2003, 7, 700-706.
https://doi.org/10.1021/op0340661

[15]. Friesner, R. A.; Murphy, R. B.; Repasky, M. P.; Frye, L. L.; Greenwood, J. R.; Halgren, T. A.; Sanschagrin, P. C.; Mainz, D. T. J. Med. Chem. 2006, 49, 6177-6196.
https://doi.org/10.1021/jm051256o

[16]. Rosenstock, J.; Brazg, R.; Andryuk, P. J.; Lu, K.; Stein, P.; Study, S. Clin. Therap. 2006, 28, 1556-1568.
https://doi.org/10.1016/j.clinthera.2006.10.007

[17]. Yamaguchi, T.; Sakairi, K.; Yamaguchi, E.; Tada, N.; Itoh, A. RSC Adv. 2016, 6, 56892-56895.
https://doi.org/10.1039/C6RA04073J

[18]. Ghavami, A.; Johnston, B. D.; Pinto, B. M. J. Org. Chem. 2001, 66, 2312-2317.
https://doi.org/10.1021/jo001444g

[19]. Andrews, J. S.; Weimar, T.; Frandsen, T. P.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 1995, 117, 10799-10804.
https://doi.org/10.1021/ja00149a002

[20]. Flanagan, P. R.; Forstner, G. G. Biochem. J. 1978, 173, 553-563.
https://doi.org/10.1042/bj1730553

[21]. Balaraju, T.; Kumar, A.; Bal, C.; Chattopadhyay, D.; Jena, N.; Bal, N. C.; Sharon, A. Struc. Chem. 2013, 24, 1499-1512.
https://doi.org/10.1007/s11224-012-0181-1

[22]. Khan, I.; Ibrar, A.; Abbas, N.; Saeed, A. Eur. J. Med. Chem. 2014, 76, 193-244.
https://doi.org/10.1016/j.ejmech.2014.02.005

[23]. Gurram, V.; Garlapati, R.; Thulluri, C.; Madala, N.; Kasani, K. S.; Machiraju, P. K.; Doddapalla, R.; Addepally, U.; Gundla, R.; Patro, B. Med. Chem. Res. 2015, 24, 2227-2237.
https://doi.org/10.1007/s00044-014-1293-5

[24]. Iino, T.; Sasaki, Y.; Bamba, M.; Mitsuya, M.; Ohno, A.; Kamata, K.; Hosaka, H.; Maruki, H.; Futamura, M.; Yoshimoto, R. Bioorg. Med. Chem. Lett. 2009, 19, 5531-5538.
https://doi.org/10.1016/j.bmcl.2009.08.064

[25]. Thiyagarajan, A.; Salim, M. T.; Balaraju, T.; Bal, C.; Baba, M.; Sharon, A. Bioorg. Med. Chem. Lett. 2012, 22, 7742-7747.
https://doi.org/10.1016/j.bmcl.2012.09.072

[26]. Gurram, V.; Akula, H. K.; Garlapati, R.; Pottabathini, N.; Lakshman, M. K. Adv. Syn. Catal. 2015, 357, 451-462.
https://doi.org/10.1002/adsc.201400889

[27]. Liu, J. F.; Lee, J.; Dalton, A. M.; Bi, G.; Yu, L.; Baldino, C. M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005, 46, 1241-1244.
https://doi.org/10.1016/j.tetlet.2005.01.008

[28]. Hikawa, H.; Ino, Y.; Suzuki, H.; Yokoyama, Y. J. Org. Chem. 2012, 77, 7046-7051.
https://doi.org/10.1021/jo301282n

[29]. Garlapati, R.; Pottabathini, N.; Gurram, V.; Kasani, K. S.; Gundla, R.; Thulluri, C.; Machiraju, P. K.; Chaudhary, A. B.; Addepally, U.; Dayam, R.; Chunduri, V. R.; Patro, B. Org. Biomol. Chem. 2013, 11, 4778-4791.
https://doi.org/10.1039/c3ob40636a

[30]. Kasula, M.; Balaraju, T.; Toyama, M.; Thiyagarajan, A.; Bal, C.; Baba, M.; Sharon, A. Chem. Med. Chem. 2013, 8, 1673-1680.

[31]. Balaraju, T.; Kumar, A.; Bal, C.; Chattopadhyay, D.; Jena, N.; Bal, N. C.; Sharon, A. Struc. Chem. 2013, 24(5), 1499-1512.
https://doi.org/10.1007/s11224-012-0181-1

[32]. Bal, N. C.; Jena, N.; Sopariwala, D.; Balaraju, T.; Shaikh, S.; Bal, C.; Sharon, A.; Gyorke, S.; Periasamy, M. Biochem. J. 2011, 435(2), 391-399.
https://doi.org/10.1042/BJ20101771

[33]. Thiyagarajan, A.; Salim, M. T. A.; Balaraju, T.; Bal, C.; Baba, M.; Sharon, A. Bioorg. Med. Chem. Lett. 2012, 22(24), 7742-7747.
https://doi.org/10.1016/j.bmcl.2012.09.072

[34]. Kumar, A.; Chakravarty, H.; Bal, N. C.; Balaraju, T.; Jena, N.; Misra, G.; Bal, C.; Balaraju, T.; Jena, N.; Misra, G.; Pieroni, E.; Periasamy, M.; Sharon, A. Mol. Biosys. 2013, 9(7), 1949-1957.
https://doi.org/10.1039/c3mb25588c

[35]. Bal, N. C.; Jena, N.; Chakravarty, H.; Kumar, A.; Chi, M.; Balaraju, T.; Rawale, S. V.; Sharon, A.; Periasamy, M. Biopolymers 2015, 103(1), 15-22.
https://doi.org/10.1002/bip.22534

[36]. Talasila, M.; Bavirisetti, H.; Chimakurthy, J.; Candasamy, M. J. Health Sci. 2014, 4(3), 162-168.
https://doi.org/10.17532/jhsci.2014.163

Supporting Agencies

Science and Engineering Research Board (SERB) India and Gandhi Institute of Technology and Management (GITAM) University School of Science, Departmet of Chemistry, Hyderabad
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