242
Views
28
CrossRef citations to date
0
Altmetric
Reviews

Recent advances on structural modifications of benzothiazoles and their conjugate systems as potential chemotherapeutics

, , , &
Pages 619-635 | Published online: 12 Apr 2012

Bibliography

  • Lagunin A, Stepanchikova A, Filimonov D, Poroikov V. PASS: prediction of activity spectra for biologically active substances. Bioinformatics 2000;16:747-8
  • Nogradi A, Vrbova G. The effect of riluzole treatment in rats on the survival of injured adult and grafted embryonic motoneurons. Eur J Neurosci 2001;13:113-18
  • Bae HJ, Lee YS, Kang DW, Neuroprotective effect of low dose riluzole in gerbil model of transient global ischemia. Neurosci Lett 2000;294:29-32
  • Benavides J, Camelin JC, Mitrani N, 2-Amino-6-trifluoromethoxy benzothiazole, a possible antagonist of excitatory amino acid neurotransmission--II. Biochemical properties. Neuropharmacology 1985;24:1085-92
  • Amnerkar ND, Bhusari KP. Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetyl-pyrazolin derivatives of aminobenzothiazole. Eur J Med Chem 2010;45:149-59
  • Deng XQ, Song MX, Wei CX, Synthesis and anticonvulsant activity of 7-alkoxy-triazolo-[3, 4-b]benzo[d]thiazoles. Med Chem 2010;6:313-20
  • Siddiqui N, Ahsan W. Benzothiazole incorporated barbituric acid derivatives: synthesis and anticonvulsant screening. Arch Pharm (Weinheim) 2009;342:462-8
  • Chopade RS, Bahekar RH, Khedekar PB, Synthesis and anticonvulsant activity of 3-(6-substituted-benzothiazol-2-yl)-6-phenyl-[1,3]-xazinane-2-thiones. Arch Pharm (Weinheim) 2002;335:381-8
  • Jimonet P, Audiau F, Barreau M, Riluzole series. Synthesis and in vivo "antiglutamate" activity of 6-substituted-2-benzothiazolamines and 3-substituted-2-imino-benzothiazolines. J Med Chem 1999;42:2828-43
  • Burger A, Sawhey SN. Antimalarials. 3. Benzothiazole amino alcohols. J Med Chem 1968;11:270-3
  • Hori N, Tsukamoto G, Imamura A, Novel disease-modifying antirheumatic drugs. I. Synthesis and antiarthritic activity of 2-(4-methylphenyl)benzothiazoles. Chem Pharm Bull (Tokyo) 1992;40:2387-90
  • Palmer PJ, Trigg RB, Warrington JV. Benzothiazolines as antituberculous agents. J Med Chem 1971;14:248-51
  • Huang Q, Mao J, Wan B, Searching for new cures for tuberculosis: design, synthesis, and biological evaluation of 2-methylbenzothiazoles. J Med Chem 2009;52:6757-67
  • Waisser K, Dolezal M, Sidoova E, Biological side-effects of potential anti-tubercular agents. XIV. Relation between the chemical structure, antitubercular activity and hepatotoxicity of 2-alkylthio-6-(2-chlorobenzamido) benzothiazoles. Ceska Farm 1988;37:437-9
  • Patel NB, Khan IH, Rajani SD. Antimycobacterial and antimicrobial study of new 1,2,4-triazoles with benzothiazoles. Arch Pharm (Weinheim) 2010;343:692-9
  • Lee YR, Jin GH, Lee SM, Inhibition of TNF-alpha-mediated inflammatory responses by a benzodioxolylacetylamino-linked benzothiazole analog in human fibroblast-like synoviocytes. Biochem Biophys Res Commun 2011;408:625-9
  • Jin GH, Li H, An S, Design, synthesis and activity of benzothiazole-based inhibitors of NO production in LPS-activated macrophages. Bioorg Med Chem Lett 2010;20:6199-02
  • Paramashivappa R, Phani Kumar P, Subba Rao PV, Srinivasa Rao A. Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors. Bioorg Med Chem Lett 2003;13:657-60
  • Al-Tel TH, Al-Qawasmeh RA, Zaarour R. Design, synthesis and in vitro antimicrobial evaluation of novel Imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole motifs. Eur J Med Chem 2011;46:1874-81
  • Stella A, Segers K, De Jonghe S, Synthesis and antibacterial evaluation of a novel series of 2-(1,2-dihydro-3-oxo-3H-pyrazol-2-yl)benzothiazoles. Chem Biodivers 2011;8:253-65
  • Nam NH, Dung PT, Thuong PT. Synthesis and biological evaluation of a series of 2-(substitutedphenyl)benzothiazoles. Med Chem 2011;7:127-34
  • Gilani SJ, Khan SA, Siddiqui N, Synthesis and in vitro antimicrobial activity of novel N-(6-chlorobenzo[d]thiazol-2-yl) hydrazine carboxamide derivatives of benzothiazole class. J Enzyme Inhib Med Chem 2011;26:332-40
  • Franchini C, Muraglia M, Corbo F, Synthesis and biological evaluation of 2-mercapto-1,3-benzothiazole derivatives with potential antimicrobial activity. Arch Pharm (Weinheim) 2009;342:605-13
  • Latrofa A, Franco M, Lopedota A, Structural modifications and antimicrobial activity of N-cycloalkenyl-2-acylalkylidene-2,3-dihydro-1,3-benzothiazoles. Farmaco 2005;60:291-7
  • Youssef AM, Noaman E. Synthesis and evaluation of some novel benzothiazole derivatives as potential anticancer and antimicrobial agents. Arzneimittelforschung 2007;57:547-53
  • Singh T, Srivastava VK, Saxena KK, Synthesis of new thiazolyl thiazolidinylbenzothiazoles and thiazolylazetidinylbenzothiazoles as potential insecticidal, antifungal, and antibacterial agents. Arch Pharm (Weinheim) 2006;339:466-72
  • Gagos M, Menestrina G, Niewiadomy A, Gruszecki WI. Molecular organization of the antifungal and anticancer drug 2-(2,4-dihydroxyphenylo)-5,6-dichlorobenzothiazole in solution and in monolayers: an effect of pH. J Photochem. Photobiol B 2005;80:101-6
  • Chohan ZH, Scozzafava A, Supuran CT. Zinc complexes of benzothiazole-derived Schiff bases with antibacterial activity. J Enzyme Inhib Med Chem 2003;18:259-63
  • Bujdakova H, Kuchta T, Sidoova E, Gvozdjakova A. Anti-Candida activity of four antifungal benzothiazoles. FEMS Microbiol Lett 1993;112:329-33
  • Havrylyuk D, Mosula L, Zimenkovsky B, Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety. Eur J Med Chem 2010;45:5012-21
  • Kamal A, Srikanth YVV, Khan MNA, 2-Anilinonicotinyl linked 2-aminobenzothiazoles and [1,2,4]triazolo[1,5-b] [1,2,4]benzothiadiazine conjugates as potential mitochondrial apoptotic inducers. Bioorg Med Chem 2011;23:7136-50
  • Trapani G, Franco M, Latrofa A, Synthesis, in vitro and in vivo cytotoxicity, and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazo[2,1-b]benzothiazoles. Eur J Pharm Sci 2001;14:209-16
  • Amino N, Ideyama Y, Yamano M, YM-201627: an orally active antitumour agent with selective inhibition of vascular endothelial cell proliferation. Cancer Lett 2006;238:119-27
  • Kumbhare RM, Kumar KV, Ramaiah MJ, Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents. Eur J Med Chem 2011;46:4258-66
  • Huang S, Liu Z, Tian SS, Discovery of 2-amino-6-carboxamidobenzothiazoles as potent Lck inhibitors. Bioorg Med Chem Lett 2008;18:2324-8
  • Khokra SL, Arora K, Mehta H, Common methods to synthesize benzothiazole derivatives and their medicinal significance: a review. Int J Curr Pharm Res 2011;2:1356-77
  • Chaudhary P, Sharma PK, Sharma A, Varshney J. Recent advances in pharmacological activity of benzothiazole derivatives. Int J Curr Pharm Res 2010;2:5-11
  • Sanap MS, Dighe NS, Pattan SR, Benzothiazole it's current pharmacological profile and methods of synthesis. Pharmacology Online 2010;1:238-44
  • Priyanka Sharma NK, Jha KK. Benzothiazole: the molecule of diverse biological activities. Int J Curr Pharm Res 2010;2:1-6
  • Yadav PS, Devprakash Senthilkumar GP. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharm Sci Drug Res 2011;3:1-7
  • Caleta I, Kralj M, Branimir BB, Novel cyano- and amidinobenzothiazole derivatives: synthesis, antitumour evaluation, and X-ray and quantitative structure-activity relationship (QSAR) analysis. J Med Chem 2009;52:1744-56
  • Yates PC, Mccall CJ, Stevens MFG. Structural Studies on Benxothiazoles. Crystal and molecular structure of 5,6-dimethoxy-Z-(4-methoxyphenyl)-benzothiazole and molecular orbital calculations on related compounds. Tetrahedron 1991;47:6493-02
  • Stevens MF, McCall CJ, Lelieveld P, Structural studies on bioactive compounds. 23. Synthesis of polyhydroxylated 2-phenylbenzothiazoles and a comparison of their cytotoxicities and pharmacological properties with genistein and quercetin. J Med Chem 1994;37:1689-95
  • Shi DF, Bradshaw TD, Wrigley S, Antitumour benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J Med Chem 1996;39:3375-84
  • Bradshaw TD, Shi DF, Schultz RJ, Influence of 2-(4-aminophenyl)benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo. Br J Cancer 1998;78:421-9
  • Bradshaw TD, Stevens MF, Westwell AD. The discovery of the potent and selective antitumour agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds. Curr Med Chem 2001;8:203-10
  • Brantley E, Trapani V, Alley MC, Fluorinated 2-(4-amino-3-methylphenyl) benzothiazoles induce CYP1A1 expression, become metabolized, and bind to macromolecules in sensitive human cancer cells. Drug Metab Dispos 2004;32:1392-01
  • O'Brien SE, Browne HL, Bradshaw TD, Antitumour benzothiazoles. Frontier molecular orbital analysis predicts bioactivation of 2-(4-aminophenyl)benzothiazoles to reactive intermediates by cytochrome P4501A1. Org Biomol Chem 2003;1:493-7
  • Chua MS, Shi DF, Wrigley S, Antitumour benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumour activities of the parent amines. J Med Chem 1999;42:381-92
  • Kashiyama E, Hutchinson I, Chua M-S, J Med Chem 1999;42:4172-84
  • Shi DF, Bradshaw TD, Chua MS, Antitumour benzothiazoles. Part 15: the synthesis and physico-chemical properties of 2-(4-aminophenyl)benzothiazole sulfamate salt derivatives. Bioorg Med Chem Lett 2001;11:1093-5
  • Hutchinson I, Chua MS, Browne HL, Antitumour benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles. J Med Chem 2001;44:1446-55
  • Trapani V, Patel V, Leong CO, DNA damage and cell cycle arrest induced by 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203, NSC 703786) is attenuated in aryl hydrocarbon receptor deficient MCF-7 cells. Br J Cancer 2003;88:599-05
  • Bradshaw TD, Bibby MC, Double JA, Preclinical evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles. Mol Cancer Ther 2002;1:239-46
  • Hutchinson I, Jennings SA, Vishnuvajjala BR, Antitumour benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumour 2-(4-aminophenyl)benzothiazole amino acid prodrugs. J Med Chem 2002;45:744-7
  • Bradshaw TD, Westwell AD. The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate. Curr Med Chem 2004;11:1009-21
  • Bradshaw TD, Chua MS, Browne HL, In vitro evaluation of amino acid prodrugs of novel antitumour 2-(4-amino-3-methylphenyl)benzothiazoles. Br J Cancer 2002;86:1348-54
  • Mukherjee A, Martin SG. In vitro cytotoxicity of Phortress against colorectal cancer. Int J Oncol 2006;29:1287-94
  • Hutchinson I, Bradshaw TD, Matthews CS, Antitumour benzothiazoles. Part 20: 3'-cyano and 3'-alkynyl-substituted 2-(4'-aminophenyl)benzothiazoles as new potent and selective analogues. Bioorg Med Chem Lett 2003;13:471-4
  • Choi SJ, Park HJ, Lee SK, Solid phase combinatorial synthesis of benzothiazoles and evaluation of topoisomerase II inhibitory activity. Bioorg Med Chem 2006;14:1229-35
  • Gong B, Hong F, Kohm C, Synthesis and SAR of 2-arylbenzoxazoles, benzothiazoles and benzimidazoles as inhibitors of lysophosphatidic acid acyltransferase-beta. Bioorg Med Chem Lett 2004;14:1455-9
  • Racane L, Kralj M, Suman L, Novel amidino substituted 2-phenylbenzothiazoles: synthesis, antitumour evaluation in vitro and acute toxicity testing in vivo. Bioorg Med Chem 2010;18:1038-44
  • Devmurari VP, Shivanand P, Jivani NP, Synthesis and anticancer activity of some novel2-substituted benzothiazole derivatives. Int J Chem Tech Res 2010;2:681-9
  • Bhuva HA, Parmar RR, Kini SG. Synthesis and cytotoxic activity of some novel substituted 2-phenyl-1,3-benzothiazoles. J Pharm Res 2010;3:980-3
  • Prabhu PP, Shastry CS, Pande S, Pai A. Synthesis,characterization and biological evaluation of novel aryl benzothiazole derivatives. J Pharm Res 2011;4:2209-11
  • Hu WP, Chen YK, Liao CC, Synthesis, and biological evaluation of 2-(4-aminophenyl)benzothiazole derivatives as photosensitizing agents. Bioorg Med Chem 2010;18:6197-07
  • Tzanopoulou S, Sagnou M, Paravatou-Petsotas M, Evaluation of Re and (99m)Tc complexes of 2-(4'-aminophenyl)benzothiazole as potential breast cancer radio pharmaceuticals. J Med Chem 2010;53:4633-41
  • Tzanopoulou S, Pirmettis IC, Patsis G, Synthesis, characterization, and biological evaluation of M(I)(CO)3(NNO) complexes (M = Re, 99mTc) conjugated to 2-(4-amino phenyl)benzothiazole as potential breast cancer radiopharmaceuticals. J Med Chem 2006;49:5408-10
  • Mortimer CG, Wells G, Crochard JP, Antitumour benzothiazoles. 26.(1) 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 2006;49:179-85
  • Aiello S, Wells G, Stone EL, Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). J Med Chem 2008;51:5135-9
  • Wells G, Bradshaw TD, Diana P, Antitumour benzothiazoles. Part 10: the synthesis and antitumour activity of benzothiazole substituted quinol derivatives. Bioorg Med Chem Lett 2000;10:513-15
  • Wells G, Berry JM, Bradshaw TD, 4-Substituted 4-hydroxycyclohexa-2,5-dien-1-ones with selective activities against colon and renal cancer cell lines. J Med Chem 2003;46:532-41
  • Lion CJ, Matthews CS, Wells G, Antitumour properties of fluorinated benzothiazole-substituted hydroxycyclohexa-2,5-dienones ('quinols'). Bioorg Med Chem Lett 2006;16:5005-8
  • Huang ST, Hsei IJ, Chen C. Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles. Bioorg Med Chem 2006;14:6106-19
  • Viegas-Junior C, Danuello A, da Silva Bolzani V, Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 2007;14(17):1829-52
  • Xie L, Zhai X, Ren L, Design, synthesis and antitumor activity of novel artemisinin derivatives using hybrid approach. Chem Pharm Bull (Tokyo) 2011;59:984-90
  • Decker M. Hybrid molecules incorporating natural products: applications in cancer therapy, neurodegenerative disorders and beyond. Curr Med Chem 2011;18:1464-75
  • Breen EC, Walsh JJ. Tubulin-targeting agents in hybrid drugs. Curr Med Chem 2010;17:609-39
  • Mehta G, Singh V. Hybrid systems through natural product leads: an approach towards new molecular entities. Chem Soc Rev 2002;31:324-34
  • Kamal A, Reddy KS, Khan MN, Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates. Bioorg Med Chem 2010;18:4747-61
  • Kamal A, Khan MN, Reddy KS, Synthesis, structural characterization and biological evaluation of novel [1,2,4]triazolo[1,5-b][1,2,4]benzothiadiazine-benzothiazole conjugates as potential anticancer agents. Chem Biol Drug Des 2008;71:78-86
  • Kamal A, Kumar BA, Suresh P, An efficient one-pot synthesis of benzothiazolo-4beta-anilino-podophyllotoxin congeners: DNA topoisomerase-II inhibition and anticancer activity. Bioorg Med Chem Lett 2011;21:350-3
  • Tasler S, Muller O, Wieber T, N-substituted 2'-(aminoaryl)benzothiazoles as kinase inhibitors: hit identification and scaffold hopping. Bioorg Med Chem Lett 2009;19:1349-56
  • Tasler S, Muller O, Wieber T, Substituted 2-arylbenzothiazoles as kinase inhibitors: hit-to-lead optimization. Bioorg Med Chem 2009;17:6728-37
  • Bradshaw TD, Wrigley S, Shi DF, 2-(4-Aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro anti-tumour activity. Br J Cancer 1998;77:745-52
  • Stanley LA, Coroneos E, Cuff R, Immunochemical detection of arylamine N-acetyltransferase in normal and neoplastic bladder. J Histochem Cytochem 1996;44:1059-67
  • Loaiza-Perez AI, Trapani V, Hose C, Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumour agent 2-(4-amino-3-methylphenyl) benzothiazole. Mol Pharmacol 2002;61:13-19
  • Hose CD, Hollingshead M, Sausville EA, Monks A. Induction of CYP1A1 in tumour cells by the antitumour agent 2-[4-amino-3-methylphenyl]-5-fluoro-benzothiazole: a potential surrogate marker for patient sensitivity. Mol Cancer Ther 2003;2:1265-72
  • Chua MS, Kashiyama E, Bradshaw TD, Role of Cyp1A1 in modulation of antitumour properties of the novel agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203, NSC 674495) in human breast cancer cells. Cancer Res 2000;60:5196-03
  • Bradshaw TD, Trapani V, Vasselin DA, Westwell AD. The aryl hydrocarbon receptor in anticancer drug discovery: friend or foe? Curr Pharm Des 2002;8:2475-90
  • Whitlock JP Jr. Induction of cytochrome P4501A1. Annu Rev Pharmacol Toxicol 1999;39:103-25
  • Hose C, Riviera M, Sausville E, Monks A. Induction of cytochrome P450 CYP1A1 and cytochrome P450 CYP1B1 by 2-(4-amino-3-methylphenyl)benzothiazole (BZ) in 60 human tumour cell lines: correlation with BZ toxicity. Proc Am Assoc Cancer Res 2001;42(2749):511
  • Tan BS, Tiong KH, Muruhadas A, CYP2S1 and CYP2W1 mediate 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW-610, NSC 721648) sensitivity in breast and colorectal cancer cells. Mol Cancer Ther 2011;10:1982-92
  • Leong CO, Gaskell M, Martin EA, Heydon RT. Antitumour 2-(4-aminophenyl) benzothiazoles generate DNA adducts in sensitive tumour cells in vitro and in vivo. Br J Cancer 2003;88:470-7
  • Leong CO, Suggitt M, Swaine DJ, In vitro, in vivo, and in silico analyses of the antitumour activity of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazoles. Mol Cancer Ther 2004;3:1565-75
  • Brantley E, Antony S, Kohlhagen G, Anti-tumor drug candidate 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole induces single-strand breaks and DNA-protein cross-links in sensitive MCF-7 breast cancer cells. Cancer Chemother Pharmacol 2006;58:62-72
  • Novak M, Chakraborty M. Reactions of a putative metabolite of the model antitumor drug 2-(4-aminophenyl)benzothiazole with purines and pyrimidines. J Phys Org Chem 2011;24:960-8

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.