Organocatalyzed solvent free an efficient novel synthesis of 2,4,5-trisubstituted imidazoles for α-glucosidase inhibition to treat diabetes

Bioorganic Chemistry

Volumn 58, Issue , 2015, Pages 65-71

  Yar, Muhammad ^a   Bajda, Marek ^b,c   Shahzad, Sohail ^a,d   Ullah, Nisar ^e   Gilani, Mazhar Amjad ^a   Ashraf, Muhammad ^d   Rauf, Abdul ^d   Shaukat, Ayesha ^d  

^a Process and Energy Systems Engineering Center PRESTIGE   (Pakistan)

^b UNIVERSITY OF WARSAW   (Poland)

^c JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^d THE ISLAMIA UNIVERSITY OF BAHAWALPUR   (Pakistan)

^e KING FAHD UNIVERSITY OF PETROLEUM AND MINERALS   (Saudi Arabia)

Author keywords

Baker's yeast; Diabetes; Imidazoles; Molecular modeling; Organocatalysis; glucosidase inhibition

Indexed keywords

2 (2 METHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3 METHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (3,4 DIMETHOXYPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (4 CHLOROPHENYL) 4,5 DIPHENYL 1H IMIDAZOLE; 2 (4,5 DIPHENYL 1H IMIDAZOL 2 YL) 6 METHOXYPHENOL; 2 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 2,4,5 TRIPHENYL 1H IMIDAZOLE; 4 (4,5 DIPHENYL 1H IMIDAZOL 2 YL)PHENOL; 4,5 DIPHENYL 2 (PROPAN 2 YL) 1H IMIDAZOLE; ALDEHYDE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; AMMONIUM ACETATE; ANTIDIABETIC AGENT; BENZALDEHYDE; BENZILIC ACID DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG; GLYCOSIDASE INHIBITOR; SOLVENT;

ANTIDIABETIC ACTIVITY; ARTICLE; BIOCATALYSIS; CATALYSIS; CATALYST; CONCENTRATION (PARAMETERS); CRYSTAL STRUCTURE; DIABETES MELLITUS; DRUG HYDROLYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; ENZYME INHIBITION; ENZYME MECHANISM; HYDROGEN BOND; HYDROPHILICITY; IC50; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; NONHUMAN; NUCLEOPHILICITY; PROTON TRANSPORT; SACCHAROMYCES CEREVISIAE; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

CATALYSIS; DIABETES MELLITUS; GLYCOSIDE HYDROLASE INHIBITORS; HUMANS; IMIDAZOLES; MODELS, MOLECULAR; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84914674502     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2014.11.006     Document Type: Article

References (58)

1. Y.-G. Chen, P. Li, P. Li, R. Yan, X.-Q. Zhang, and Y. Wang Molecules 18 2013 4221 4232
2. G. Danaei, M. Finucane, Y. Lu, G. Singh, M. Cowan, and C. Paciorek Lancet 378 2011 31 40
3. N. Asano Glycobiology 13 2003 93R 104R
4. R.R. Holman, C.A. Cull, and R.C. Turner Diabetes Care 22 1999 960 964
5. M.J. Humphries, K. Matsumoto, S.L. White, and K. Olden Cancer Res. 46 1986 5215 5222
6. H. Park, K.Y. Hwang, K.H. Oh, Y.H. Kim, J.Y. Lee, and K. Kim Bioorg. Med. Chem. 16 2008 284 292
7. S.J. Storr, L. Royle, C.J. Chapman, U.M.A. Hamid, J.F. Robertson, and A. Murray Glycobiology 18 2008 456 462
8. D.P. Gamblin, E.M. Scanlan, and B.G. Davis Chem. Rev. 109 2008 131 163
9. 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
10. A.J. Rawlings, H. Lomas, A.W. Pilling, M.J.R. Lee, D.S. Alonzi, and J. Rountree Chem. Biol. Chem. 10 2009 1101 1105
11. D. Schmidt, W. Frommer, B. Junge, L. Muller, W. Wingender, and E. Truscheit Naturwissenschaften 64 1977 535 536
12. L.J. Scott, and C.M. Spencer Miglitol Drugs 59 2000 521 549
13. T. Matsuo, H. Odaka, and H. Ikeda Am. J. Clin. Nutr. 55 1992 314S-7S
14. N. Asano, K. Oseki, E. Tomioka, H. Kizu, and K. Matsui Carbohydr. Res. 259 1994 243 255
15. P. Hollander Drugs 44 1992 47 53
16. S. Adisakwattana, K. Sookkongwaree, S. Roengsumran, A. Petsom, N. Ngamrojnavanich, and W. Chavasiri Bioorg. Med. Chem. Lett. 14 2004 2893 2896
17. S. Sou, S. Mayumi, H. Takahashi, R. Yamasaki, S. Kadoya, and M. Sodeoka Bioorg. Med. Chem. Lett. 10 2000 1081 1084
18. J. Lee, J. Laydon, P. McDonnell, T. Gallagher, S. Kumar, D. Green, S.W. Land vatter, J.E. Strickler, M.M. McLaughlin, I.R. Siemens, S.M. Fisher, G.P. Livi, J.R. White, J.L. Adams, and P.R. Young Nature 372 1994 739 746
19. A.K. Takle, M.J. Brown, S. Davies, D.K. Dean, G. Francis, and A. Gaiba Bioorg. Med. Chem. Lett. 16 2006 378 381
20. I.K. Khanna, R.M. Weier, Y. Yu, X.D. Xu, F.J. Koszyk, and P.W. Collins J. Med. Chem. 40 1997 1634 1647
21. J.H. Lange, H.H. van Stuivenberg, H.K. Coolen, T.J. Adolfs, A.C. McCreary, and H.G. Keizer J. Med. Chem. 48 2005 1823 1838
22. T.F. Gallagher, S.M. Fier-Thompson, R.S. Garigipati, M.E. Sorenson, J.M. Smietana, and D. Lee Bioorg. Med. Chem. Lett. 5 1995 1171 1176
23. K.P. Chooi, S.R. Galan, R. Raj, J. McCullagh, S. Mohammed, and L.H. Jones J. Am. Chem. Soc. 136 2014 1698 1701
24. S. Samai, G.C. Nandi, P. Singh, and M. Singh Tetrahedron 65 2009 10155 10161
25. A. Teimouri, and A.N. Chermahini J. Mol. Catal. A: Chem. 346 2011 39 45
26. H. Zang, Q. Su, Y. Mo, B.-W. Cheng, and S. Jun Ultrason. Sonochem. 17 2010 749 751
27. A.R. Khosropour Ultrason. Sonochem. 15 2008 659 664
28. M. Xia, and Y-d. Lu J. Mol. Catal. A: Chem. 265 2007 205 208
29. S.E. Wolkenberg, D.D. Wisnoski, W.H. Leister, Y. Wang, Z. Zhao, and C.W. Lindsley Org. Lett. 6 2004 1453 1456
30. M.V. Chary, N.C. Keerthysri, S.V. Vupallapati, N. Lingaiah, and S. Kantevari Catal. Commun. 9 2008 2013 2017
31. L. Wang, and C. Cai Monatshefte für Chemie-Chemical Monthly 140 2009 541 546
32. M. Saffari Jourshari, M. Mamaghani, F. Shirini, K. Tabatabaeian, M. Rassa, and H. Langari Chin. Chem. Lett. 24 2013 993 996
33. B.F. Mirjalili, A. Bamoniri, and M.A. Mirhoseini Scientia Iranica, Trans. C: Chem. Chem. Eng. 20 2013 587 591
34. H. Roy, M. Rahman, and P. Pramanick Indian J. Chem. Section B-Org. Chem. Incl. Med. Chem. 52 2013 153 159
35. D.I. MaGee, M. Bahramnejad, and M. Dabiri Tetrahedron Lett. 54 2013 2591 2594
36. R.S. Joshi, P.G. Mandhane, M.U. Shaikh, R.P. Kale, and C.H. Gill Chin. Chem. Lett. 21 2010 429 432
37. M. Yar, M. Bajda, L. Shahzadi, S.A. Shahzad, M. Ahmed, M. Ashraf, U. Alam, I.U. Khan, and A.F. Khan Bioorg. Chem. 54 2014 96 104
38. S.A. Shahzad, M. Yar, M. Bajda, B. Jadoon, Z.A. Khan, S.A.R. Naqvi, A.J. Shaikh, K. Hayat, A. Mahmood, N. Mahmood, and S. Filipek Bioorg. Med. Chem. 22 2014 1008 1015
39. M. Yar, M. Bajda, R.A. Mehmood, L.R. Sidra, N. Ullah, L. Shahzadi, M. Ashraf, T. Ismail, S.A. Shahzad, Z.A. Khan, S.A.R. Naqvi, and N. Mahmood Lett. Drug Des. Discov. 11 2014 331 338
40. M. Yar, L.R. Sidra, E. Pontiki, N. Mushtaq, M. Ashraf, R. Nasar, I.U. Khan, N. Mahmood, S.A.R. Naqvi, Z.A. Khan, and S.A. Shahzad J. Iran. Chem. Soc. 11 2014 369 378
41. S. Riaz, I.U. Khan, M. Yar, M. Ashraf, T.U. Rehman, A. Shaukat, S.B. Jamal, V.C.M. Duarte, and M.J. Alves Bioorg. Chem. 57 2014 148 154
42. K. Ramesh, S.N. Murthy, K. Karnakar, Y. Nageswar, K. Vijayalakhshmi, and B.L. Prabhavathi Devi Tetrahedron Lett. 53 2012 1126 1129
43. M. Balba, N.A. El-Hady, N. Taha, N. Rezki, and E.S.H. El Ashry Eur. J. Med. Chem. 46 2011 2596 2601
44. R. Schowen, J. Liebman, and A. Greenberg Mechanistic Principles of Enzyme Activity 1988 VCH New York 119
45. M.L. Sinnott Chem. Rev. 90 1990 1171 1202
46. A.J. Kirby Crit. Rev. Biochem. Mol. Biol. 22 1987 283 315
47. M.P. Dale, W.P. Kopfler, I. Chait, and L.D. Byers Biochemistry 25 1986 2522 2529
48. R. Field, A.H. Haines, E. Chrystal, and M.C. Luszniak Biochem. J. 274 1991 885 889
49. F.J. Luque, J.M. López, M. Orozco. Perspective on "electrostatic interactions of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects". Theoretical Chemistry Accounts: Springer; 2001. p. 343-5.
50. E. Scrocco, and J. Tomasi Adv. Quant. Chem. 11 1978 115 193
51. P. Politzer, P.R. Laurence, and K. Jayasuriya Environ. Health Perspect. 61 1985 191
52. Corina on-line, < http://www.molecular-networks.com/online-demos/corina-demo >.
53. Sybyl-X 1.1, Tripos, St. Louis, MO, USA, 2010.
54. Gold 5.1, The Cambridge Crystallographic Data Centre, Cambridge, UK, 2011.
55. PyMOL 0.99rc6, DeLano Scientific LLC: Palo Alto, CA, USA, 2006.
56. M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, et al. Gaussian 09, Rev. C. 01, Gaussian. Inc., Wallingford CT, 2009.
57. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
58. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785