Triazinoindole analogs as potent inhibitors of α-glucosidase: Synthesis, biological evaluation and molecular docking studies

Bioorganic Chemistry

Volumn 58, Issue , 2015, Pages 81-87

  Rahim, Fazal ^a   Ullah, Khadim ^a   Ullah, Hayat ^a   Wadood, Abdul ^b   Taha, Muhammad ^c,d   Rehman, Ashfaq Ur ^b   Uddin, Imad ^a   Ashraf, Muhammad ^e   Shaukat, Ayesha ^e   Rehman, Wajid ^a   Hussain, Shafqat ^f   Khan, Khalid Mohammed ^f  

^a HAZARA UNIVERSITY   (Pakistan)

^b ABDUL WALI KHAN UNIVERSITY   (Pakistan)

^c UNIVERSITI TEKNOLOGI MARA   (Malaysia)

^d Faculty of Civil Engineering (UiTM)   (Malaysia)

^e THE ISLAMIA UNIVERSITY OF BAHAWALPUR   (Pakistan)

^f UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

Molecular docking; Synthesis; Triazinoindole; Glucosidase inhibition

Indexed keywords

2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (2 METHOXYPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (3 BROMOPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (3 FLOUROPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (3 HYDROXYPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (3 METHOXYPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (4 BROMOPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (4 METHOXYPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (4 NITROPHENYL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 (BIPHENYL 4 YL)ETHANONE; 2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO) 1 PHENYLPROPANE 1 ONE; 3 [2 (5H [1,2,4]TRIAZINO[5,6 B]INDOL 3 YLTHIO)ACETYL) 2H CHROMEN 2 ONE; ACARBOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; INDOLE DERIVATIVE; TRIAZINE; TRIAZINOINDOLE DERIVATIVE; UNCLASSIFIED DRUG; GLYCOSIDASE INHIBITOR; TRIAZINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; COMPARATIVE STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INHIBITION; EVALUATION STUDY; IC50; MOLECULAR DOCKING; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; SYNTHESIS;

GLYCOSIDE HYDROLASE INHIBITORS; INDOLES; INHIBITORY CONCENTRATION 50; MOLECULAR DOCKING SIMULATION; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TRIAZINES;

EID: 84919941245     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2014.12.001     Document Type: Article

References (32)

1. J. Burani, and L. Rao Good Carbs, Bad Carbs. Weight and Optimum Health 2002 NY Marlowe & Co.
2. H. Park, K.Y. Hwang, Y.H. Kim, K.H. Oh, J.Y. Lee, and K. Kim Bioorg. Med. Chem. Lett. 18 2008 3711 3715
3. H. Ali, P.J. Houghton, and A. Soumyanath J. Ethnopharmacol. 107 2006 449 455
4. M. Bhat, S.S. Zinjarde, S.Y. Bhargava, A.R. Kumar, and B.N. Joshi Evi. Based Complement Alternate Med. 2011 810-207
5. G.A. Bray, and F.L. Greenway Endocr. Rev. 20 1999 805 879
6. U. saqib, and M. Imran Siddiqi Int. J. Integ. Bio. 2 2008 115 121
7. J.L. Chiasson, R.G. Josse, and R. Gomis Lancet 359 2002 2072 2077
8. A. Mehta, Z. zitzmann, P.M. Rudd, T.M. Block, and R.A. Dwek FEBS Lett. 430 1998 17 22
9. A. Metha, N. Zitzmann, P.M. Rudd, T.M. Block, and R.A. Dwek FEBS Lett. 430 1998 17
10. R.A. Gruters, J.J. Neefjes, M. Tersmetti, R.E.W. De Goede, A. Tulp, H.G. Huisman, F. Miedeme, and H.C. Ploegh Nature 330 1987 74
11. S. Shelke, and S. Bhosale Bioorg. Med. Chem. Lett. 20 2010 4661
12. A. Monge, J.A. Palop, C. Ramierz, M. Font, and A.E. Fernandez Eur. J. Chem. 26 1991 179
13. J.L. Kgokong, P.P. Smith, and G.M. Matsabisa Bioorg. Med. Chem. 13 2005 2935 2942
14. U.M. Aswar, P.P. Kalshetti, S.M. Shelke, S.H. Bhosale, and S.L. Bodhankar Asian J. Trop. Biomed. 2 2012 992
15. A.B. Tomchin, O.Y. Uryupov, T.I. Zhukova, and T.A. Kuznetsova Pharma. Chem. J. 31 1997 19
16. J.M.Z. Gladych, J.H. Hunt, D. Jack, R.F. Haff, J.J. Boyle, R.C. Stewart, and R. Ferlanto J. Nature. 221 1969 286
17. J.J. Boyle, W.G. Raupp, F.J. Stanfield, R.F. Haff, E.C. Dick, D.D. Alessio, C.R. Dick, and N.Y. Ann Acad. Sci. 173 1970 477
18. J.M. Gwaltney Proc. Soc. Exp. Biol. Med. 133 1970 1148
19. R.F. Haff, W.B. Flagg, J.J. Gallo, J.R.E. Hoover, J.A. Miller, C.A. Pinto, and J.F. Pagano Proc. Soc. Exp. Biol. Med. 141 1972 475
20. W. Jamil, S. Perveen, S.A.A. Shah, M. Taha, N.H. Ismail, S. Perveen, N. Ambreen, K.M. Khan, and M.I. Choudhary Molecules 19 2014 8788 8802
21. K.M. Khan, S.M. Saad, N.N. Shaikh, S Hussain, M.I. Fakhri, S. Perveen, M. Taha, and M.I. Choudhary Bioorg. Med. Chem. 22 2014 3449 3454
22. Z.S. Saify, A. Kamil, S. Akhtar, M. Taha, A. Khan, K.M. Khan, S. Jahan, F. Rahim, S. Perveen, and M.I. Choudhary Med. Chem. Res. 23 2014 4447 4454
23. K.M. Khan, N. Ambreen, M. Taha, S.A. Halim, Zaheer-ul-Haq, S. Naureen, S. Rasheed, S. Perveen, S. Ali, and M.I. Choudhary J. Comput. Aided Mol. Des. 28 2014 577 585
24. K.M. Khan, F. Rahim, A. Wadood, M. Taha, M. Khan, S. Naureen, N. Ambreen, S. Hussain, S. Perveen, and M.I. Choudhary Bioorg. Med. Chem. Lett. 24 2014 1825 1829
25. K.M. Khan, F. Naz, M. Taha, A. Khan, S. Perveen, M.I. Choudhary, and W. Voelter Eur. J. Med. Chem. 74 2014 314 323
26. Y. Liu, L. Zou, L. Ma, W.H. Chen, B. Wang, and Z.L. Xu Bioorg. Med. Chem. 14 2006 5683
27. Y. Liu, L. Ma, W.H. Chen, B. Wang, and Z.L. Xu Bioorg. Med. Chem. 15 2007 2810
28. S.B. Ferreira, A.C. Sodero, M.F. Cardoso, E.S. Lima, C.R. Kaiser, F.P. Silva, and V.F. Ferreira Jr J. Med. Chem. 53 2010 2364
29. J. Park, S. Ko, and H. Park Bull. Korean Chem. Soc. 29 2008 921
30. A. Roujeinikova, C. Raasch, S. Sedelnikova, W. Liebl, and D.W. Rice J. Mol. Biol. 321 2002 149
31. L.R. Guerreiro, E.P. Carreiro, L. Fernandes, T.A. Cardote, R. Moreira, A.T. Caldeira, R.C. Guedes, and A. Burke Bioorg. Med. Chem. 21 2013 1911
32. K. Yamamoto, H. Miyake, M. Kusunoki, and S. Osaki FEBS J. 277 2010 4205