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 - Tập 92 - Trang 387-400 - 2015
Muhammad Taha1, Nor Hadiani Ismail1, Salima Lalani2, M. Fatmi3, Atia‐tul Wahab2, Salman Siddiqui2, Naveed Ahmed Khan2, Syahrul Imran1, M. Iqbal Choudhary2
1Faculty of Applied Science UiTM, 40450 Shah Alam, Selangor, Malaysia
2H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
3Department of Biosciences, COMSATS Institute of Information Technology (CIIT), Park Road, Chak Shahzad, Islamabad 45600, Pakistan

Tóm tắt

Từ khóa


Tài liệu tham khảo

Cao, 2002, Modulation of recombinant and native neuronal SK channels by the neuro protective drug riluzole, Eur. J. Pharmacol., 449, 47, 10.1016/S0014-2999(02)01987-8

Anzini, 2010, 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, 734, 10.1021/jm901375r

Khan, 2011, Synthesis of novel inhibitors of b-glucuronidase based on benzothiazole skeleton and study of their binding affinity by molecular docking, Bioorg. Med. Chem., 19, 4286, 10.1016/j.bmc.2011.05.052

Das, 2003, Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors, Bioorg. Med. Chem. Lett., 13, 2587, 10.1016/S0960-894X(03)00511-0

Turan-Zitouni, 2004, Synthesis of some 2-[(benzazole-2-yl)thioacetylamino]thiazole derivatives and their antimicrobial activity and toxicity, Eur. J. Med. Chem., 39, 267, 10.1016/j.ejmech.2003.11.001

Ban, 1998, Novel antiallergic and antiinflammatory agents. Part I: synthesis and pharmacology of glycolic amide derivatives, Bioorg. Med. Chem., 6, 1069, 10.1016/S0968-0896(98)00065-0

Hall, 1999, 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, 115, 10.1002/(SICI)1521-4184(19994)332:4<115::AID-ARDP115>3.0.CO;2-G

Bradshaw, 2004, The development of the antitumour benzothiazole prodrug, phortress, as a clinical candidate, Curr. Med. Chem., 11, 1009, 10.2174/0929867043455530

Westwell, 2004, The therapeutic potential of aryl Hydrocarbon Receptor (AhR) agonists in anticancer drug development, Drugs Future, 29, 479, 10.1358/dof.2004.029.05.804556

Chua, 1999, 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, 381, 10.1021/jm981076x

Hutchinson, 2002, Antitumor benzothiazoles: synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs, J. Med. Chem., 45, 744, 10.1021/jm011025r

Wells, 2000, Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives, Bioorg. Med. Chem. Lett., 10, 513, 10.1016/S0960-894X(00)00027-5

Hose, 2003, Induction of CYP1A1 in tumor cells by the antitumor agents 2-[4-amino-3-methylphenyl]-5-flouro-benzothiazole: a potential surrogate marker for patient sensitivity, Mol. Can. Ther., 2, 1265

Leong, 2003, Antitumour 2-(4-aminophenyl)benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo, Br. J. Cancer., 88, 470, 10.1038/sj.bjc.6600719

Brantley, 2005, 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, 137, 10.1097/00001813-200502000-00004

Mortimer, 2006, 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, 179, 10.1021/jm050942k

Sato, 2000, Assessment of potential mutagenic activities of a novel benzothiazole MAO-A inhibitor E2011 using Salmonella typhimurium YG1029, Mutat. Res., 472, 163, 10.1016/S1383-5718(00)00139-X

Tuylu, 2007, Synthesis and mutagenicity of 2-aryl-substitute (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, 626, 10.2478/s11756-007-0122-4

Khan, 2013, Acylhydrazide Schiff bases: synthesis and antiglycation activity, J. Pak. Chem. Soc., 35, 929

Khan, 2013, Synthesis of benzophenonehydrazone Schiff bases and their in vitro antiglycating activities, Med. Chem., 9, 588, 10.2174/1573406411309040013

Taha, 2014, Synthesis of 4-methoxybenzoylhydrazones and evaluation of their antiglycation activity, Molecules, 19, 1286, 10.3390/molecules19011286

Taha, 2014, 4-[5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl]benzohydrazide, Molbank, M826, 10.3390/M826

Anouar, 2013, Antioxidant properties of phenolic Schiff bases: structure–activity relationship and mechanism of action, J. Comput. Aided Mol. Des., 27, 951, 10.1007/s10822-013-9692-0

Taha, 2013, Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazones, Molecules, 18, 10912, 10.3390/molecules180910912

Khan, 2012, 2,4,6-trichlorophenylhydrazine Schiff bases as DPPH radical and super oxide anion scavengers, Med. Chem., 8, 452, 10.2174/1573406411208030452

Taha, 2013, Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanial activity, Bioorg. Med. Chem. Lett., 23, 3463, 10.1016/j.bmcl.2013.03.051

Imran, 2014, Synthesis of novel bisindolylmethane Schiff bases and their antibacterial activity, Molecules, 19, 11722, 10.3390/molecules190811722

Sundriyal, 2006, Current Advances in antifungal targets and drug development, Curr. Med. Chem., 13, 1321, 10.2174/092986706776873023

Popp, 1961, Synthesis of potential anticancer agents. V. Schiff bases and related compounds, J. Org. Chem., 26, 3858, 10.1021/jo01068a056

Jain, 2007, Synthesis and evaluation of schiff bases for anticonvulsant and Behavioral Depressant properties, Cent. Nerv. Syst. Agents Med. Chem., 7, 200, 10.2174/187152407781669143

Gan, 2013, Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer's disease, Med. Chem. Res., 22, 4069, 10.1007/s00044-012-0416-0

Priyadharsini, 2012, docking, synthesis, characterization and evaluation of novel cdk2 inhibitors: benzothiazole derivatives, Int. J. Pharm. Pharm. Sci., 4, 574

Geronikaki, 2003, Novel thiazolyl, thiazolinyl and benzothiazolyl Schiff bases as possible lipoxygenase's inhibitors and anti-inflammatory agents, Il Farm., 58, 489, 10.1016/S0014-827X(03)00065-X

Kabeer, 2001, Synthesis and antimicrobial activity of some Schiff bases from benzothiazoles, Asian J. Chem., 13, 496

Bruni, 1970, Further kinetic and structural characterization of the lysosomal α-D-glucoside glucohydrolase from cattle liver, Biochim. Biophys. Acta., 212, 470, 10.1016/0005-2744(70)90253-6

Flanagan, 1978, Purification of rat intestinal maltase/glucoamylase and its anomalous dissociation either by heat or by low pH, Biochem.. J., 173, 553, 10.1042/bj1730553

“EC 3.2.1.20”. ExPASy. Retrieved 1 March 2012.

Chiba, 1997, Molecular mechanism in α-glucosidase and glucoamylase, Biosci. Biotechnol. Biochem., 61, 1233, 10.1271/bbb.61.1233

Mehrani, 1993, Characterization of α-glucosidases from rainbow trout liver, Arch. Biochem. Biophys., 306, 188, 10.1006/abbi.1993.1499

FDA News Release FDA. Retrieved 1 March 2012.

Yoshimizu, 2008, 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, 68, 10.1016/j.cca.2008.02.014

Kim, 2000, Inhibition of alpha-glucosidase and amylase by luteolin, a flavonoid, Biosci. Biotechnol. Biochem., 64, 2458, 10.1271/bbb.64.2458

Bischoff, 1995, The mechanism of alpha-glucosidase inhibition in the management of diabetes, Clin. Invest. Med., 18, 303

Özkay, 2010, Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem., 45, 3293, 10.1016/j.ejmech.2010.04.012

El-Hamouly, 2011, Synthesis and antitumor activity of some new N-substituted-sulfonyl, 1,2,4-triazole, N-substituted-benzylidene and pyrrole derivatives attached to 4-(benzo[d]thiazol-2-yl)benzohydrazide, Der Pharma Chem., 3, 293

Taha, 2014, Synthesis of novel derivatives of 4-methylbenzimidazole and evaluation of their biological activities, Eur. J. Med. Chem., 84, 731, 10.1016/j.ejmech.2014.07.078

Jamil, 2014, Phenoxyacetohydrazide schiff bases: β-glucuronidase inhibitors, Molecules, 19, 8788, 10.3390/molecules19078788

Khan, 2014, Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones, Bioorg. Med. Chem., 22, 3449, 10.1016/j.bmc.2014.04.039

Saify, 2014, 2-(2'-Pyridyl) benzimidazole derivatives and their urease inhibitory activity, Med. Chem. Res., 23, 4447, 10.1007/s00044-014-1015-z

Khan, 2014, Structure-Based design, synthesis and biological evaluation of ß-glucuronidase inhibitors, J. Comput. Aided Mol. Des., 28, 577, 10.1007/s10822-014-9745-z

Khan, 2014, Evaluation of Bisindole as potent β-glucuronidase inhibitors: synthesis and in silico based studies, Bioorg. Med. Chem. Lett., 24, 1825, 10.1016/j.bmcl.2014.02.015

Khan, 2014, Synthesis and in vitro urease inhibitory activity of N,N'-disubsituted thioureas, Eur. J. Med. Chem., 74, 314, 10.1016/j.ejmech.2014.01.001

Brindis, 2011, (Z)-3-butylidenephthalide from ligusticum porteri, an alpha-glucosidase inhibitor, J. Nat. Prod., 74, 314, 10.1021/np100447a

Porto, 2012, Pharmacological enhancement of α-glucosidase by the allosteric chaperone n-acetylcysteine, Mol. Ther., 20, 2201, 10.1038/mt.2012.152

Liu, 2013, Binding mechanism and synergetic effects of xanthone derivatives as noncompetitive α-glucosidase inhibitors: a theoretical and experimental study, J. Phys. Chem. B, 117, 13464, 10.1021/jp4067235

J.E. Oben. Methods and related compositions using specific flavonoids and indanes to reduce weight and inhibit lipase, α-amylase and α-glucosidase activity in mammals. Gatew. Health Alliances, Inc. (US 8,394,860 B2; March 12, 2013).

Liu, 2013, Inhibiting enzymatic starch digestion by the phenolic compound diboside A: a mechanistic and in silico study, Food Res. Int., 54, 595, 10.1016/j.foodres.2013.07.062

Carreiro, 2014, 3-hydroxypyrrolidine and (3, 4)-dihydroxypyrrolidine derivatives: inhibition of rat intestinal α-glucosidase, Bioorg. Chem., 54, 81, 10.1016/j.bioorg.2014.04.007

Guerreiro, 2013, Five-membered iminocyclitol α-glucosidase inhibitors: synthetic, biological screening and in silico studies, Bioorg. Med. Chem., 21, 1911, 10.1016/j.bmc.2013.01.030

Khan, 2014, Synthesis and molecular docking studies of potentn α-glucosidase inhibitors based on biscoumarin skeleton, Eur. J. Med. Chem., 81, 245, 10.1016/j.ejmech.2014.05.010

Allouche, 2011, Graphical user interface for computational chemistry softwares, J. Comput. Chem., 32, 174, 10.1002/jcc.21600

Trott, 2010, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading, J. Comput. Chem., 31, 455, 10.1002/jcc.21334

William, 1996, VMD-visual molecular dynamics, J. Mol. Graph., 14, 33, 10.1016/0263-7855(96)00018-5

2013