Synthesis of novel inhibitors of α-glucosidase based on the benzothiazole skeleton containing benzohydrazide moiety and their molecular docking studies

European Journal of Medicinal Chemistry

Volumn 92, Issue , 2015, Pages 387-400

  Taha, Muhammad ^a,b   Ismail, Nor Hadiani ^a,b   Lalani, Salima ^c   Fatmi, Muhammad Qaiser ^d   Atia Tul Wahab, ^c   Siddiqui, Salman ^c   Khan, Khalid Mohammed ^c   Imran, Syahrul ^a,b   Choudhary, Muhammad Iqbal ^c  

^a UNIVERSITI TEKNOLOGI MARA   (Malaysia)

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

^c UNIVERSITY OF KARACHI   (Pakistan)

^d Department of Biosciences COMSATS Institute of Information Technology ^*  (Pakistan)

Author keywords

Benzothiazole derivatives; DFT calculations; Docking studies; Physico chemical properties; Glucosidase

Indexed keywords

4 (BENZO[D]THIAZOL 2 YL) N' ((FURAN 2 YL)METHYLENE)BENZOHYDRAZIDE; 4 (BENZO[D]THIAZOL 2 YL) N' ((PYRIDIN 3 YL)METHYLENE) BENZOHYDRAZIDE; 4 (BENZO[D]THIAZOL 2 YL) N' ((PYRIDIN 4 YL)METHYLENE) BENZOHYDRAZIDE; 4 (BENZO[D]THIAZOL 2 YL) N' ((THIOPHEN 2 YL)METHYLENE) BENZOHYDRAZIDE; 4 (BENZO[D]THIAZOL 2 YL) N' BENZYLIDENEBENZOHYDRAZIDE; 4 (BENZO[D]THIAZOL 2 YLL) N' ((PYRIDIN 2 YL)METHYLENE) BENZOHYDRAZIDE; ALPHA GLUCOSIDASE INHIBITOR; BENZOTHIAZOLE; HYDRAZIDE DERIVATIVE; METHYL 4 ((4 (BENZO[D]THIAZOL 2 YL)BENZOYLIMINO) METHYL)BENZOATE; N (4 HYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (2 HYDROXY4 METHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (2 HYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (2,3 DIHYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (2,4 DIHYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (2,4,6 TRIHYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2YL)BENZOHYDRAZIDE; N' (3 BROMO 4 FLUOROBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (3 BROMO 4 HYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (3 HYDROXY 4 METHOXYBENZYLIDENE) 4 (BENZO[D] THIAZOL 2 YL)BENZOHYDRAZIDE; N' (3 HYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (3 METHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (3,4 DIHYDROXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (3,4 DIIMETHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2YL)BENZOHYDRAZIDE; N' (3,5 DIMETHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2YL)BENZOHYDRAZIDE; N' (4 CHLOROBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (4 FLUOROBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N' (4 HYDROXY 3 METHOXYBENZYLIDENE) 4 (BENZO[D] THIAZOL 2 YL)BENZOHYDRAZIDE; N' (4 METHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL) BENZOHYDRAZIDE; N' (4 NITROBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; N'(2 HYDROXY 5 METHOXYBENZYLIDENE) 4 (BENZO[D]THIAZOL 2 YL)BENZOHYDRAZIDE; UNCLASSIFIED DRUG; ALPHA GLUCOSIDASE; BENZOTHIAZOLE DERIVATIVE; GLYCOSIDASE INHIBITOR;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING SITE; CARBOXY TERMINAL SEQUENCE; DENSITY FUNCTIONAL THEORY; DRUG DESIGN; DRUG INHIBITION; DRUG SYNTHESIS; ENERGY; ENZYME ACTIVITY; HYDROGEN BOND; IC50; MOLECULAR DOCKING; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALPHA-GLUCOSIDASES; BENZOTHIAZOLES; DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCOSIDE HYDROLASE INHIBITORS; HUMANS; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84920848432     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.01.009     Document Type: Article

References (64)

1. Y.J. Cao, J.C. Dreixler, J.J. Couey, K.M. Houamed, Modulation of recombinant and native neuronal SK channels by the neuro protective drug riluzole, Eur. J. Pharmacol. 449 (2002) 47-54
2. M. Anzini, A. Chelini, A. Mancini, A. Cappelli, M. Frosini, L. Ricci, M. Valoti, J. Magistretti, L. Castelli, A. Giordani, F. Makovec, S. Vomero, Synthesis and biological evaluation of amidine, guanidine, and thiourea derivatives of 2- amino(6-trifluoromethoxy)benzothiazole as neuroprotective agents potentially useful in brain diseases, J. Med. Chem. 53 (2010) 734-744
3. K.M. Khan, F. Rahim, S.A. Halim, M. Taha, M. Khan, S. Perveen, Zaheer-Ul-Haq, M.A. Mesaik, M.I. Choudhary, Synthesis of novel inhibitors of b-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking, Bioorg. Med. Chem. 19 (2011) 4286-4294
4. J. Das, R.V. Moquin, J. Lin, C. Liu, A.M. Doweyko, H.F. DeFex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors, Bioorg. Med. Chem. Lett. 13 (2003) 2587-2590
5. G. Turan-Zitouni, Ş. Demirayak, A. Özdemir, Z.A. Kaplancikl, M.T. Yildiz, Synthesis of some 2-[(benzazole-2-yl)thioacetylamino]thiazole derivatives and their antimicrobial activity and toxicity, Eur. J. Med. Chem. 39 (2004) 267-272
6. M. Ban, H. Taguchi, T. Katsushima, M. Takahashi, K. Shinoda, A. Watanabe, T. Tominaga, Novel antiallergic and antiinflammatory agents. Part I: synthesis and pharmacology of glycolic amide derivatives, Bioorg. Med. Chem. 6 (1998) 1069-1076
7. I.H. Hall, N.J. Peaty, J.R. Henry, J. Easmon, G. Heinisch, G. Pürstinger, Investigations on the mechanism of action of the novel antitumor agents 2- benzothiazolyl, 2-benzoxazolyl, and 2-benzimidazolyl hydrazones derived from 2-acetylpyridine, Arch. Pharm. 332 (1999) 115-123
8. T.D. Bradshaw, A.D. Westwell, The development of the antitumour benzothiazole prodrug, phortress, as a clinical candidate, Curr. Med. Chem. 11 (2004) 1009-1021
9. A.D. Westwell, The therapeutic potential of aryl Hydrocarbon Receptor (AhR) agonists in anticancer drug development, Drugs Future 29 (2004) 479-491
10. M.S. Chua, D.F. Shi, S. Wrigley, T.D. Bradshaw, I. Hutchinson, P. Nicholas, D.A. Barret, L.A. Stanley, M.F.G. Stevens, Antitumor benzothiazoles: synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines, J. Med. Chem. 42 (1999) 381-392
11. I. Hutchinson, S.A. Jennings, B.R. Vishnuvajjala, A.D. Wetsell, M.F.G. Stevens, Antitumor benzothiazoles: synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs, J. Med. Chem. 45 (2002) 744-747
12. G. Wells, T.D. Bradshaw, P. Diana, A. Seaton, D.F. Shi, A.D. Westwell, M.F.G. Stevens, Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives, Bioorg. Med. Chem. Lett. 10 (2000) 513-515, 10
13. C.D. Hose, M.E. Hollingshead, A. Sausville, A. Monks, Induction of CYP1-1 in tumor cells by the antitumor agents 2-[4-amino-3-methylphenyl]-5-flourobenzothiazole: a potential surrogate marker for patient sensitivity, Mol. Can. Ther. 2 (2003) 1265-1272
14. C.O. Leong, M. Gaskell, E.A. Martin, R.T. Heydon, P.B. Farmer, M.C. Bibby, P.A. Cooper, J.A. Double, T.D. Bradshaw, M.F.G. Stevens, Antitumour 2-(4- aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo, Br. J. Cancer. 88 (2003) 470-477
15. E. Brantley, V. Patel, S.F. Stinson, V. Trapani, C.D. Hose, H.P. Ciolino, G.C. Yeh, J.S. Gutkind, E.A. Sausville, A.I. Loaiza-Pérez, The antitumor drug candidate 2- (4-amino-3-methylphenyl)-5-fluorobenzothiazole induces NF-[kappa]B activity in drug-sensitive MCF-7 cells, AntiCancer Drugs 16 (2005) 137-143
16. C.G. Mortimer, G. Wells, J.P. Crochard, E.L. Stone, T.D. Bradshaw, M.F.G. Stevens, A.D. Westwell, Antitumor benzothiazoles. 26. 2-(3,4- dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-Arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines, J. Med. Chem. 49 (2006) 179-185
17. G. Sato, S. Asakura, A. Hakura, Y. Tsutsui-Hiyoshi, N. Kobayashi, K. Tsukidate, Assessment of potential mutagenic activities of a novel benzothiazole MAO-A inhibitor E2011 using Salmonella typhimurium YG1029, Mutat. Res. 472 (2000) 163-169
18. B.A. Tuylu, H.S. Zeytinoglu, I. Isikdag, Synthesis and mutagenicity of 2-arylsubstitute (o-hydroxy-, m-bromo-, o-methoxy-, o-nitro-phenyl or 4-pyridyl) benzothiazole derivatives on Salmonella typhimurium and human lymphocytes exposed in vitro, Biologia 62 (2007) 626-632
19. K.M. Khan, M. Taha, F. Rahim, M.I. Fakhri, W. Jamil, M. Khan, S. Rasheed, A. Karim, S. Perveen, M.I. Choudhary, Acylhydrazide Schiff bases: synthesis and antiglycation activity, J. Pak. Chem. Soc. 35 (2013) 929-937
20. K.M. Khan, F. Rahim, N. Ambreen, M. Taha, M. Khan, H. Jahan, Najeebullah, A. Shaikh, S. Iqbal, S. Perveen, M.I. Choudhary, Synthesis of benzophenonehydrazone Schiff bases and their in vitro antiglycating activities, Med. Chem. 9 (2013) 588-595
21. M. Taha, H. Naz, S. Rasheed, N.H. Ismail, A.A. Rahman, S. Yousuf, M.I. Choudhary, Synthesis of 4-methoxybenzoylhydrazones and evaluation of their antiglycation activity, Molecules 19 (2014) 1286-1301
22. M. Taha, N.H. Ismail, S. Imran, K.M. Khan, 4-[5-(2-methoxyphenyl)-1,3,4- oxadiazol-2-yl]benzohydrazide, Molbank (2014) M826
23. E. Anouar, S. Raweh, I. Bayach, M. Taha, M.S. Baharudin, F.D. Meo, M.H. Hasan, A. Adam, N.H. Ismail, J.F. Weber, P. Trouillas, Antioxidant properties of phenolic Schiff bases: structureeactivity relationship and mechanism of action, J. Comput. Aided Mol. Des. 27 (2013) 951-964
24. M. Taha, N.H. Ismail, W. Jamil, S. Yousuf, F.M. Jaafar, M.I. Ali, S.M. Kashif, E. Hussain, Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones, Molecules 18 (2013) 10912-10929
25. K.M. Khan, Z. Shah, V.U. Ahmad, M. Khan, M. Taha, S. Ali, S. Perveen, M.I. Choudhary, W. Voelter, 2,4,6-trichlorophenylhydrazine Schiff bases as DPPH radical and super oxide anion scavengers, Med. Chem. 8 (2012) 452-461
26. M. Taha, M.S. Baharudin, N.H. Ismail, K.M. Khan, F.M. Jaafar, Samreen, S. Siddiqui, M.I. Choudhary, Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanial activity, Bioorg. Med. Chem. Lett. 23 (2013) 3463-3466
27. S. Imran, M. Taha, N.H. Ismail, K.M. Khan, F. Naz, M. Hussain, S. Tauseef, Synthesis of novel bisindolylmethane Schiff bases and their antibacterial activity, Molecules 19 (2014) 11722-11740
28. S. Sundriyal, R.K. Sharma, R. Jain, Current Advances in antifungal targets and drug development, Curr. Med. Chem. 13 (2006) 1321-1335
29. F.D. Popp, W.J. Kirsch, Synthesis of potential anticancer agents. V. Schiff bases and related compounds, J. Org. Chem. 26 (1961) 3858-3860
30. J.S. Jain, R.S. Srivastava, N. Aggarwal, R. Sinha, Synthesis and evaluation of schiff bases for anticonvulsant and Behavioral Depressant properties, Cent. Nerv. Syst. Agents Med. Chem. 7 (2007) 200-204
31. C. Gan, L. Zhou, Z. Zhao, H. Wang, Benzothiazole Schiff-bases as potential imaging agents for b-amyloid plaques in Alzheimer′s disease, Med. Chem. Res. 22 (2013) 4069-4074
32. R. Priyadharsini, A.J. Suresh, M. Sathish, S. Kavitha, A.J.S. Thanuja, docking, synthesis, characterization and evaluation of novel cdk2 inhibitors: benzothiazole derivatives, Int. J. Pharm. Pharm. Sci. 4 (2012) 574-584
33. A. Geronikaki, D. Hadjipavlou-Litina, M. Amourgianou, Novel thiazolyl, thiazolinyl and benzothiazolyl Schiff bases as possible lipoxygenase′s inhibitors and anti-inflammatory agents, Il Farm. 58 (2003) 489-495
34. A.S. Kabeer, M.A. Baseer, N.A. Mote, Synthesis and antimicrobial activity of some Schiff bases from benzothiazoles, Asian J. Chem. 13 (2001) 496-500
35. C.B. Bruni, V. Sica, F. Auricchio, I. Covelli, Further kinetic and structural characterization of the lysosomal a-D-glucoside glucohydrolase from cattle liver, Biochim. Biophys. Acta. 212 (1970) 470-477
36. P.R. Flanagan, G.G. Forstner, Purification of rat intestinal maltase/glucoamylase and its anomalous dissociation either by heat or by low pH, Biochem. J. 173 (1978) 553-563
37. EC 3.2.1.20. ExPASy. Retrieved 1 March 2012
38. S. Chiba, Molecular mechanism in a-glucosidase and glucoamylase, Biosci. Biotechnol. Biochem. 61 (1997) 1233-1239
39. H. Mehrani, K.B. Storey, Characterization of a-glucosidases from rainbow trout liver, Arch. Biochem. Biophys. 306 (1993) 188-194
40. FDA News Release FDA. Retrieved 1 March 2012
41. M. Yoshimizu, Y. Tajima, F. Matsuzawa, S. Aikawa, K. Iwamoto, T. Kobayashi, T. Edmunds, K. Fujishima, D. Tsuji, K. Itoh, M. Ikekita, I. Kawashima, K. Sugawara, N. Ohyanagi, T. Suzuki, T. Togawa, K. Ohno, H. Sakuraba, Binding parameters and thermodynamics of the interaction of imino sugars with a recombinant human acid alpha-glucosidase (alglucosidase alfa): insight into the complex formation mechanism, Clin. Chim. Acta. 391 (2008) 68-73
42. J.S. Kim, C.S. Kwon, K.H. Son, Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid, Biosci. Biotechnol. Biochem. 64 (2000) 2458-2461
43. H. Bischoff, The mechanism of alpha-glucosidase inhibition in the management of diabetes, Clin. Invest. Med. 18 (1995) 303-311
44. Y. Özkay, Y. Tanah, H. Karaka,-I. Iskdág, Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem. 45 (2010) 3293-3298
45. W.S. El-Hamouly, K.M. Amin, S.A. El-Assaly, E.A.A. El-Meguid, Synthesis and antitumor activity of some new N-substituted-sulfonyl, 1,2,4-triazole, Nsubstituted- benzylidene and pyrrole derivatives attached to 4-(benzo[d] thiazol-2-yl)benzohydrazide, Der Pharma Chem. 3 (6) (2011) 293-306
46. M. Taha, N.H. Ismail, W. Jamil, H. Rashwan, S.M. Kashif, A.A. Sain, M.I. Adenan, E.H. Anouar, M. Ali, F. Rahim, K.M. Khan, Synthesis of novel derivatives of 4- methylbenzimidazole and evaluation of their biological activities, Eur. J. Med. Chem. 84 (2014) 731-738
47. W. Jamil, S. Perveen, S.A.A. Shah, M. Taha, N.H. Ismail, S. Perveen, N. Ambreen, K.M. Khan, M.I. Choudhary, Phenoxyacetohydrazide schiff bases: b-glucuronidase inhibitors, Molecules 19 (2014) 8788-8802
48. K.M. Khan, S.M. Saad, N.N. Shaikh, S. Hussain, M.I. Fakhri, S. Perveen, M. Taha, M.I. Choudhary, Synthesis and b-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones, Bioorg. Med. Chem. 22 (2014) 3449-3454
49. Z.S. Saify, A. Kamil, S. Akhtar, M. Taha, A. Khan, K.M. Khan, S. Jahan, F. Rahim, S. Perveen, M.I. Choudhary, 2-(2′-Pyridyl) benzimidazole derivatives and their urease inhibitory activity, Med. Chem. Res. 23 (2014) 4447-4454
50. K.M. Khan, N. Ambreen, M. Taha, S.A. Halim, Zaheer-ul-Haq, S. Naureen, S. Rasheed, S. Perveen, S. Ali, M.I. Choudhary, Structure-Based design, synthesis and biological evaluation of β-glucuronidase inhibitors, J. Comput. Aided Mol. Des. 28 (2014) 577-585
51. K.M. Khan, F. Rahim, A.Wadood, M. Taha, M. Khan, S. Naureen, N. Ambreen, S. Hussain, S. Perveen, M.I. Choudhary, Evaluation of Bisindole as potent bglucuronidase inhibitors: synthesis and in silico based studies, Bioorg. Med. Chem. Lett. 24 (2014) 1825-1829
52. K.M. Khan, F. Naz, M. Taha, A. Khan, S. Perveen, M.I. Choudhary, W. Voelter, Synthesis and in vitro urease inhibitory activity of N,N′-disubsituted thioureas, Eur. J. Med. Chem. 74 (2014) 314-323
53. F. Brindis, R. Rodríguez, R. Bye, M. Gonzalez-Andrade, R. Mata, (Z)-3- butylidenephthalide from ligusticum porteri, an alpha-glucosidase inhibitor, J. Nat. Prod. 74 (2011) 314-320
54. C. Porto, M.C. Ferrara, M. Meli, E. Acampora, V. Avolio, M. Rosa, B. Cobucci- Ponzano, G. Colombo, M. Moracci, G. Andria, G. Parenti, Pharmacological enhancement of a-glucosidase by the allosteric chaperone n-acetylcysteine, Mol. Ther. 20 (2012) 2201-2211
55. Y. Liu, L. Ma, W.-H. Chen, H. Park, Z. Ke, B. Wang, Binding mechanism and synergetic effects of xanthone derivatives as noncompetitive a-glucosidase inhibitors: a theoretical and experimental study, J. Phys. Chem. B 117 (2013) 13464-13471
56. J.E. Oben. Methods and related compositions using specific flavonoids and indanes to reduce weight and inhibit lipase, a-amylase and a-glucosidase activity in mammals. Gatew. Health Alliances, Inc. (US 8,394,860 B2; March 12, 2013
57. T. Liu, Y.M. Yip, L. Song, S. Feng, Y. Liu, F. Lai, D. Zhang, D. Huang, Inhibiting enzymatic starch digestion by the phenolic compound diboside A: a mechanistic and in silico study, Food Res. Int. 54 (2013) 595-600
58. E.P. Carreiro, P. Louro, G. Adriano, R.A. Guedes, N. Vannuchi, A.R. Costa, C.M.M. Antunes, R.C. Guedes, A.J. Burke, 3-hydroxypyrrolidine and (3, 4)- dihydroxypyrrolidine derivatives: inhibition of rat intestinal a-glucosidase, Bioorg. Chem. 54 (2014) 81-88
59. L.R. Guerreiro, E.P. Carreiro, L. Fernandes, T.A. Cardote, R. Moreira, A.T. Caldeira, R.C. Guedes, A.J. Burke, Five-membered iminocyclitol a-glucosidase inhibitors: synthetic, biological screening and in silico studies, Bioorg. Med. Chem. 21 (2013) 1911-1917
60. K.M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M.I. Fakhri, M. Junaid, W. Rehman, M. Khan, S. Perveen, M. Sajid, M.I. Choudhary, Synthesis and molecular docking studies of potentn aglucosidase inhibitors based on biscoumarin skeleton, Eur. J. Med. Chem. 81 (2014) 245-252
61. A.R. Allouche, A. Gabedit, Graphical user interface for computational chemistry softwares, J. Comput. Chem. 32 (2011) 174-182
62. O. Trott, A.J. Olson, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading, J. Comput. Chem. 31 (2010) 455-461
63. H. William, D. Andrew, S. Klaus, VMD-visual molecular dynamics, J. Mol. Graph. 14 (1996) 33-38
64. Molecular Operating Environment (MOE), 2013.08, Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2-7, 2013