Benzimidazoles as new scaffold of sirtuin inhibitors: Green synthesis, in vitro studies, molecular docking analysis and evaluation of their anti-cancer properties

European Journal of Medicinal Chemistry

Volumn 83, Issue , 2014, Pages 448-454

  Yoon, Yeong Keng ^a   Ali, Mohamed Ashraf ^a,b,c   Wei, Ang Chee ^a   Shirazi, Amir Nasrolahi ^d   Parang, Keykavous ^d   Choon, Tan Soo ^a  

^a INSTITUTE FOR RESEARCH IN MOLECULAR MEDICINE INFORMM   (Malaysia)

^b Alwar Pharmacy College   (India)

^c Sunrise University   (India)

^d UNIVERSITY OF RHODE ISLAND   (United States)

Author keywords

Anti proliferative; Benzimidazole; Green chemistry synthesis; Sirtuin

Indexed keywords

ANTINEOPLASTIC AGENT; BENZIMIDAZOLE DERIVATIVE; CAMBINOL; ETHYL 2 [ 4 (DIMETHYLAMINO)PHENYL] 1 PHENYL 1H BENZO[D]IMIDAZOL 5 CARBOXYLIC ACID; ETHYL 2 [ 4 (DIMETHYLAMINO)PHENYL] 1 [ 3 ( 2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOL 5 CARBOXYLIC ACID; HYDROGEN; SIRTUIN 1; SIRTUIN 2; TENOVIN 6; UNCLASSIFIED DRUG; HISTONE DEACETYLASE INHIBITOR; SIRTUIN; 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 2 P TOLYL 1H BENZO [D]IMIDAZOLE 5 CARBOXYLATE; 2 (4 NITROPHENYL) 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL (1,2 DISUBSTITUTED) 5 CARBOXYLATE; ETHYL 1 PHENYL 2 P TOLYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 2 PHENYL 1H BENZO [D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 1,2 DIPHENYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 BROMOPHENYL) 1 PHENYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 BROMOPHENYL) 1 [3 (2 OXOPYRROLIDIN 1 YL) PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 CHLOROPHENYL) 1 PHENYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 CHLOROPHENYL) 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 HYDROXYPHENYL) 1 PHENYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 HYDROXYPHENYL) 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 (4 NITROPHENYL) 1 PHENYL 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 [4 (DIMETHYLAMINO)PHENYL] 1 PHENYL 1H BENZO[D] IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 [4 (DIMETHYLAMINO)PHENYL] 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 [4 (TRIFLUOROMETHYL)PHENYL] 1 PHENYL 1H BENZO[D] IMIDAZOLE 5 CARBOXYLATE; ETHYL 2 [4 (TRIFLUOROMETHYL)PHENYL] 1 [3 (2 OXOPYRROLIDIN 1 YL)PROPYL] 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; HYDROLASE INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CELL PROLIFERATION; CELL TYPE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; GREEN CHEMISTRY; HCT116 CELL LINE; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; IN VITRO STUDY; LEUKEMIA; MOLECULAR DOCKING; TUMOR CELL LINE; ANTAGONISTS AND INHIBITORS; CELL SURVIVAL; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; METABOLISM; PROTEIN CONFORMATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; CELL PROLIFERATION ASSAY;

ANTINEOPLASTIC AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; GREEN CHEMISTRY TECHNOLOGY; HISTONE DEACETYLASE INHIBITORS; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN CONFORMATION; SIRTUINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84903726443     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.06.060     Document Type: Article

References (34)

1. S. Michan, and D. Sinclair Sirtuins in mammals: insights into their biological function Biochem. J. 404 2007 1 13 (Pubitemid 46788079)
2. J.M. Denu The Sir2 family of protein deacetylase Curr. Opin. Chem. Biol. 9 2005 431 440
3. D.M. Taylor, M.M. Maxwell, R. Luthi-Carter, and A.G. Kazantsev Biological and potential therapeutic roles of sirtuin deacetylases Cell. Mol. Life Sci. 65 2008 4000 4018
4. R.A. Fyre Phylogenetic classification of prokaryotic and eukaryotic Sir2-like proteins Biochem. Biophys. Res. Commun. 273 2000 793 798
5. J. Milner Cellular regulation of SIRT1 Curr. Pharm. Des. 15 2009 39 44
6. T. Inoue, M. Hiratsuka, M. Osaki, and M. Oshimura The molecular biology of mammalian SIRT proteins: SIRT2 in cell cycle regulation Cell. Cycle 6 2007 1011 1018 (Pubitemid 46708571)
7. B. Zschoernig, and U. Mahlknecht SIRTUIN 1: regulating the regulator Biochem. Biophys. Res. Commun. 376 2008 251 255
8. A. Mai, D. Rotili, S. Valente, and A.G. Kazantsev Histone deacetylase inhibitors and neurodegenerative disorders: holding the promise Curr. Pharm. Des. 15 2009 3940 3957
9. A.L. Garske, B.C. Smith, and J.M. Denu Linking SIRT2 to Parkinson's disease ACS Chem. Biol. 2 2007 529 532 (Pubitemid 350011322)
10. L.R. Saunders, and E. Verdin Sirtuins: critical regulators at the crossroads between cancer and aging Oncogene 26 2007 5489 5504 (Pubitemid 47255930)
11. L. Bosch-Presegue, and A. Vaquero The dual role of sirtuins in cancer Genes. Cancer 2 2011 648 662
12. J. Chen, Y. Zhou, S. Mueller-Steiner, L.F. Chen, H. Kwon, S. Yi, L. Mucke, and L. Gan SIRT1 protects against microglia-dependent amyloid-β toxicity through inhibiting NF-KB signaling J. Biol. Chem. 280 2005 40364 40374 (Pubitemid 41779174)
13. A.Z. Herskovits, and L. Guarente Sirtuin deacetylases in neurodegenerative diseases of aging Cell. Res. 23 2013 746 758
14. F. Yeung, J.E. Hoberg, C.S. Ramsey, M.D. Keller, D.R. Jones, R.A. Frye, and M.W. Mayo Modulation of NF-Kb-dependent transcription and cell survival by the SIRT1 deacetylase EMBO J. 23 2004 2369 2380 (Pubitemid 38954844)
15. A. Berdichevsky, and L. Guarente A stress response pathway involving sirtuins, forkheads and 14-3-3 proteins Cell. Cycle 5 2006 2588 2591 (Pubitemid 44785802)
16. M. Lakshminarasimhan, D. Rauh, M. Schutkowski, and C. Steegborn Sirt1 activation by resveratrol is substrate sequence-selective Aging 5 2013 151 154
17. C.M. Grozinger, E.D. Chao, H.E. Blackwell, D. Moazed, and S.L. Schreiber Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotype screening J. Biol. Chem. 276 2001 38837 38843
18. J. Posakony, M. Hirao, S. Stevens, J.A. Simon, and A. Bedalov Inhibitors of Sir2: evaluation of splitomicin analogues J. Med. Chem. 47 2004 2635 2644 (Pubitemid 38580099)
19. S. Lain, J.J. Hollick, J. Campbell, O.D. Staples, M. Higgins, M. Aoubala, A. McCarthy, V. Appleyard, K.E. Murray, L. Baker, A. Thompson, J. Mathers, S.J. Holland, M.J.R. Stark, G. Pass, J. Woods, D.P. Lane, and N.J. Westwood Discovery, in-vivo activity, and mechanism of action of a small molecule p53 activator Cancer Cell. 13 2008 454 463 (Pubitemid 351609441)
20. A.D. Napper, J. Hixon, T. McDonagh, K. Keavey, J.F. Pons, J. Barker, W.T. Yau, P. Amouzegh, A. Flegg, E. Hamelin, R.J. Thomas, M. Kates, S. Jones, M.A. Navia, J.O. Saunders, P.S. DiStefano, and R. Curtis Discovery of indoles as potent and selective inhibitors of the deacetylase SIRT1 J. Med. Chem. 48 2005 8045 8054 (Pubitemid 41798434)
21. M. Mader, A. de Dios, C. Shih, and B.D. Anderson Imidazolyl benzimidazoles and imidazo[4,5-b]pyridines as potent p38α MAP kinase inhibitors with excellent in vivo antiinflammatory properties Bioorg. Med. Chem. Lett. 18 2008 179 183
22. T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit Jr., and C.J. Michejda Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-aryl-substituted benzimidazoles J. Med. Chem. 40 1997 4199
23. D.A. Horton, G.T. Bourne, and M.L. Smythe The combinatorial synthesis of bicyclic privileged structures or priviledged substructures Chem. Rev. 103 2003 893 930
24. Y. Kim, M.R. Kumar, N. Park, Y. Heo, and S. Lee Copper-catalyzed, one-pot, three-component synthesis of benzimidazoles by condensation and C-N bond formation J. Org. Chem. 76 2011 9577 9583
25. M. Shen, and T.G. Driver Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides Org. Lett. 10 2008 3367 3370
26. 2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines Tetrahedron Lett. 45 2004 4185 4187 (Pubitemid 38581841)
27. L.M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence, A.J. Blake, C. Wilson, and M. Poliakoff Synthesis of benzimidazoles in high-temperature water Green. Chem. 5 2003 187 192 (Pubitemid 37487477)
28. K. Nagata, T. Itoh, H. Ishikawa, and A. Ohsawa Synthesis of 2-substituted benzimidazoles by reaction of o-phenylenediamine with aldehydes in the presence of Sc(OTf)∼3 Heterocycles 61 2003 93 96
29. S. Moniot, M. Schutkowski, and C. Steegborn Crystal structure analysis of human Sirt2 and its ADP-ribose complex J. Struct. Biol. 182 2013 136 143
30. S. Sakkiah, M. Arooj, M.R. Kumar, S.H. Eom, and K.W. Lee Identification of inhibitor binding site in human Sirtuin 2 using molecular docking and dynamics simulations PLoS One 8 2013 e51429
31. B. Heltweg, T. Gatbonton, A.D. Schuler, J. Posakony, H. Li, S. Goehle, R. Kollipara, R.A. Depinho, Y. Gu, J.A. Simon, and A. Bedalov Antitumor activity of a small-molecule inhibitor of human silent information regulator 2 enzymes Cancer Res. 66 2006 4368 4377
32. B. Peck, C.Y. Chen, K.K. Ho, P. Di Fruscia, S.S. Myatt, R.C. Coombes, M.J. Fuchter, C.D. Hsiao, and W.F. Eric Lam SIRT1 inhibitors induce cell death and p53 acetylation through targeting both SIRT1 and SIRT2 Mol. Cancer Ther. 9 2010 844 855
33. K. Fahey, L. O'Donovan, M. Carr, M.P. Carty, and F. Aldabbagh The influence of aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells Eur. J. Med. Chem. 45 2010 1873 1879
34. E. Moriarty, M. Carr, S. Bonham, M.P. Carty, and F. Aldabbagh Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents Eur. J. Med. Chem. 45 2010 3762 3769