European Journal of Chemistry

Quinazolin derivatives as emerging alpha-glucosidase inhibitors

Crossmark


Main Article Content

Ashok Reddy Ankireddy
Rambabu Gundla
Tuniki Balaraju
Venkanna Banothu
Krishna Prasad Gundla
Uma Addepally
Jithendra Chimakurthy

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.


icon graph This Abstract was viewed 1682 times | icon graph Article PDF downloaded 624 times

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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).