11,769
Views
125
CrossRef citations to date
0
Altmetric
Review Article

Benzothiazole derivatives as anticancer agents

, , , , , , & ORCID Icon show all
Pages 265-279 | Received 23 Oct 2019, Accepted 21 Nov 2019, Published online: 02 Dec 2019

References

  • Akhtar J, Khan AA, Ali Z. Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities. Eur J Med Chem 2017;5:143–89.
  • Keri SR, Patil RM, Patil AS, Budagumpi S. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. Eur J Med Chem 2015;89:207–51.
  • Gunawardana GP, Koehn FE, Lee AY, et al. Pyridoacridine alkaloids from deep water marine sponges of the family Pachastrellidae: structure revision of dercitin and related compounds and correlation with the Kuanoniamines. J Org Chem 1992;57:1523–6.
  • Jaiswal S, Mishra PA, Srivastava A. The different kinds of reaction involved in synthesis of 2-substituted 2enzothiazole and its derivatives: a review. Res J Pharm Biol Chem Sci 2012;3:631–41.
  • Bryson M, Fulton B, Benfield P. Riluzole a review of its pharmacodynamic and pharmacokinetic properties and therapeutic potential in amyotrophic lateral sclerosis. Drugs 1996;52:549–63.
  • Venkatesh P, Pandeya NS. Synthesis, characterisation and anti-inflammatory activity of some 2-amino benzothiazole derivatives. Int J ChemTech Res 2009;1:1354–8.
  • Liu Y, Wang Y, Dong G, et.al. Novel benzothiazole derivatives with a broad antifungal spectrum: design, synthesis and structure–activity relationships. Med Chem Commun 2013;4:1551–61.
  • Mats ME, Shani BG, Pasternak L, et al. Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives. J Med Chem 2013;56:5335–50.
  • Bele DS, Singhvi I. Synthesis and analgesic activity of some Mannich bases of 6-substituted-2-aminobenzothiazole. Res J Pharm and Tech 2008;1:22–4.
  • Padalkar SV, Gupta DV, Phatangare RK, et al. Synthesis of novel dipodal-benzimidazole, benzoxazole and benzothiazole from cyanuric chloride: structural, photophysical and antimicrobial studies. J Saudi Chem Soc 2014;18:262–8.
  • Cai J, Sun M, Wu X, et al. Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents. Eur J Med Chem 2013;63:702–12.
  • Delmas F, Avellaneda A, Giorgio DC, et al. Synthesis and antileishmanial activity of (1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. Eur J Med Chem 2004;39:685–90.
  • Munirajasekhar D, Himaja M, Sunil VM. Synthesis and anthelmintic activity of 2-amino-6- substituted benzothiazoles. Int Res J Pharm 2011;2:114–7.
  • Yadav SP, Devprakash D, Senthilkumar GP. Benzothiazole: different methods of synthesis and diverse biological activities. Int J Pharm Sci Drug Res 2011;3:01–7.
  • Siddiqui N, Rana A, Khan AS, et al. Synthesis of benzothiazole semicarbazones as novel anticonvulsants—the role of hydrophobic domain. Bioorg Med Chem Lett 2007;17:4178–82.
  • Shi HX, Wang Z, Xia Y, et al. Synthesis and biological evaluation of novel benzothiazole-2-thiol derivatives as potential anticancer agents. Molecules 2012;17:3933–44.
  • Leong CO, Suggitt M, Swaine DJ, et al. In vitro, in vivo, and in silico analyses of the antitumor activity of 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazoles. Mol Cancer Ther 2004;3:1565–75.
  • Mortimer CG, Wells G, Crochard JP, et al. Antitumor 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.
  • Baffy G. Hepatocellular carcinoma in type 2 diabetes: more than meets the eye. Am J Gastroenterol 2012;107:53–5.
  • McCutcheon M. Where have my eyebrows gone? Cengage learning. 2019. ISBN 07668393462001;5.
  • Anand P, Kunnumakara AB, Sundaram C, et al. Cancer is a preventable disease that requires major lifestyle changes. Pharm Res 2008;25:2097–116.
  • Kumbhare MR, Dadmal T, Kosurkar U, et al. Synthesis and cytotoxic evaluation of thiourea and N-bis-benzothiazolederivatives: a novel class of cytotoxic agents. Bioorg Med Chem Lett 2012; 22:453–5.
  • Kumbhare MR, Kumar VK, Ramaiah JM, et al. Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1- b]benzothi azoles as potential anti-cancer agents. Eur J Med Chem 2011;46:4258–66.
  • El-Damasy KA, Lee HJ, Seo HS, et al. Design and synthesis of new potent anticancer benzothiazole amides and ureas featuring pyridylamide moiety and possessing dual B-RafV600E and C-Raf kinase inhibitory activities. Eur J Med Chem 2016;115:201–16.
  • Ma J, Zhang G, Han X, et al. Synthesis and biological evaluation of benzothiazole derivatives bearing theortho hydroxy- N –acylhydrazone moiety as potent antitumor agents. Arch Pharm Chem Life Sci 2014;347:1–14.
  • Gabr TM, El-Gohary SN, El-Bendary RE, et al. Synthesis, in vitro antitumor activity and molecular modeling studies 4 of a new series of benzothiazole Schiff bases. Chin Chem Lett 2016;27:380–6.
  • Junjie AM, Gang UH, Lijun EIX, et al. Design, synthesis and biological evaluation of novel benzothiazole derivatives bearing semicarbazone moiety as antitumor agents. Chem Res Chin Univ 2015;31:958–63.
  • Yurttas L, Tay F, Demirayak S. Synthesis and antitumor activity evaluation of new 2-(4-aminophenyl)benzothiazole derivatives bearing different heterocyclic rings. J Enzyme Inhib Med Chem 2014;30:458–65.
  • Singh Y, Kaur B, Kaur A, et al. spectral studies and biological activity of 2, 3-disubstituted imidazo [2, 1-b] benzothiazole derivatives. Indian J Pharmaceut Biol Res 2018;6:1–8.
  • Al-Soud AY, Al-Sa’doni HH, Saeed B, et al. Synthesis and in vitro anti-proliferative activity of new benzothiazole derivatives. ARKIVOC 2008;2008:225–238.
  • Gurdal EE, Durmaz I, Atalay CR, Yarim M. Cytotoxic activities of some benzothiazole-piperazine derivatives. J Enzyme Inhib Med Chem 2015;30:649–54.
  • Akhtar T, Hameed S, Al-Masoudi AN, et al. In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives. Acta Pharm 2008;58:135–49.
  • Saeed S, Rashid N, Jones GP, et al. Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents. Eur J Med Chem 2010;45:1323–31.
  • Lei Q, Zhang L, Xia Y, et al. A novel benzothiazole derivative SKLB826 inhibits human hepatocellular carcinoma growth via inducing G2/M phase arrest and apoptosis. RSC Adv 2015;5:41341.
  • Racane L, Kulenovic TV, Pavelic KS, et al. Novel diamidino-substituted derivatives of phenyl benzothiazolyl and dibenzothia zolyl furans and thiophenes: synthesis, anti-proliferative and DNA binding properties. J Med Chem 2010;53:2418–32.
  • Sekar V, Perumal P, Arunachalam , Gandhimathi S. Screening of anticancer activity in newly synthesized benzothiazole derivatives. J Pharm Sci Res 2011;3:1520–4.
  • Xuejiao S, Yong X, Ningyu W, et al. A novel benzothiazole derivative YLT322 induces apoptosis via the mitochondrial apoptosis pathway in vitro with anti-tumor activity in solid malignancies. PLoS One 2013;8:e63900.
  • Kamal A, Ashraf M, Vardhan VSP, et al. Synthesis and anticancer potential of benzothiazole linked phenylpyridopyrimidinones and their diones as mitochondrial apoptotic inducers. Bioorg Med Chem Lett 2014;24:147–51.
  • Gabr TM, El-Gohary SN, El-Bendary RE, El-Kerdawy MM. Synthesis and in vitro antitumor activity of new series ofbenzothiazole and pyrimido[2,1-b]benzothiazole derivatives. Euro J Med Chem 2014;85:576–92.
  • Kumbhare MR, Dadmal LT, Devi AT, et al. Isoxazole derivatives of 6-fluoro-N-(6-methoxybenzo[d]thiazol-2-yl)benzo[d]thiazol-2-amine and N-(pyrimidin-2-yl)benzo[d]thiazol-2-amine: regulation of cell cycle and apoptosis by p53 activation via mitochondrial-dependent pathways. Med Chem Commun 2014;5:1744.
  • Waghmare SG, Chidrawar BA, Bhosale NV, et al. Synthesis and in-vitro anticancer activity of 3-cyano-6,9-dimethyl-4-imino 2-methylthio 4H-pyrimido [2,1-b] [1,3] benzothiazole and its 2-substituted derivative. J Pharm Res 2013;7:823–7.
  • Caleta I, Kralj M, Marjanovic M, et al. Novel cyano- and amidinobenzothiazole derivatives: synthesis, antitumor evaluation, and X-ray and quantitative structure-activity relationship (QSAR) analysis. J Med Chem 2009;52:1744–56.
  • Osmaniye D, Levent S, Karaduman BA, et al. Synthesis of new benzothiazole acylhydrazones as anticancer agents. Molecules 2018;23:1054.
  • Lad NP, Manohar Y, Mascarenhas M, et al. Methylsulfonyl benzothiazoles (MSBT) derivatives: search for new potential antimicrobial and anticancer agents. Bioorg Med Chem Lett 2017; 27:1319–24.
  • Sadhasivam G, Kulanthai K, Natarajan A. Synthesis and anti-cancer Studies of 2, 6-disubstituted benzothiazole derivatives. Orient J Chem 2015;31:819–26.
  • Wang Z, Shi HX, Wang J, et al. Synthesis, structure–activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers. Bioorg Med Chem Lett 2011;21:1097–101.
  • Bolelli k, Musdal Y, Aki-Yalcin E, et al. Synthesis and activity mechanism of some novel 2-substituted benzothiazoles as hGSTP1-1 enzyme inhibitors. SAR QSAR Environ Res 2017;28:927–40.
  • Corbo F, Carocci A, Armenise D, et al. Antiproliferative activity evaluation of a series of N-1,3-benzothiazol-2-ylbenzamides as novel apoptosis inducers. J Chem 2016;5:4267564.
  • Abdelgawad AM, Lamie FP, Ahmed MO. Synthesis of new quinolone derivatives linked to benzothiazole or benzoxazole moieties as anticancer and anti-oxidant agents. Med Chem 2016;6: 31–9.
  • Sarkar B, Maiti S, Jadhav RG, Paira P. Benzothiazolylquinoline conjugates as novel human A3 receptor antagonists: biological evaluations and molecular docking studies. R Soc Open Sci 2018;5:171622.
  • Tay F, Yurttaş L, Demirayak Ş. Synthesis of some N-[4-(benzothiazole-2yl) phenyl]-2-aryloxyacetamide derivatives and their anticancer activities. J Enzyme Inhib Med Chem 2012;27:515–20.
  • Noolvi NM, Patel MH, Kaur M. Benzothiazoles: search for anticancer agents. Eur J Med Chem 2012;54:447–62.
  • Havrylyuk D, Mosula L, Zimenkovsky B, et al. Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety. Eur J Med Chem 2010;45:5012–21.
  • Prabhu PP, Panneerselvam T, Shastry SC, et al. Synthesis and anticancer evaluation of 2-phenyl thiaolidinone substituted 2-phenyl benzothiazole-6-carboxylic acid derivatives. J Saudi Chem Soc 2015;19:181–5.
  • Abdelgawad AM, Belal A, Ahmed MO. Synthesis, molecular docking studies and cytotoxic screening of certain novel thiazolidinone derivatives substituted with benzothiazole or benzoxazole. J Chem. pharm Sci 2013;5:318–27.
  • Ma J, Bao G, Wang L, et al. Design, synthesis, biological evaluation and preliminary mechanism study of novel benzothiazole derivatives bearing indole-based moiety as potent antitumor agents. Eur J Med Chem 2015;96:173–86.
  • Xie X, Yan Y, Zhu N, Liu G. Benzothiazoles exhibit broad-spectrum antitumor activity: their potency, structure-activity and structure-metabolism relationships. Eur J Med Chem 2014;76:67–78.
  • Uremis N, Uremis MM, Tolun IF, et al. Synthesis of 2-substituted benzothiazole derivatives and their in vitro anticancer effects and antioxidant activities against pancreatic cancer cells. Anticancer Res 2017;37:6381–9.
  • Cindric M, Peric M, Kralj M, et al. Antibacterial and antiproliferative activity of novel 2-benzimidazolyland 2-benzothiazolyl-substituted benzo[b]thieno-2-carboxamides. Mol Divers 2018;22:637–46.
  • Nikolova Momekov G, Bakalova A, et al. Novel Ru(III) complexes with some benzothiazole derivatives: synthesis, physicochemical and pharmacological investigations. Drug Res 2015;65:317–22.
  • Yurttas L, Cavusoglu KB, Sever A, Ciftci AG. A preliminary investigation of anticanceractivity of novel benzothiazole derivatives against A549 lung carcinoma cell line. Turk J Biochem 2017;42: 217–24.
  • Oanh KTD, Hai VH, Park HS, et al. Benzothiazole-containing hydroxamic acids as histone deacetylase inhibitors and antitumor agents. Bioorg Med Chem Lett 2011;21:7509–12.
  • Rodrigues RJ, Charris J, Camacho J, et al. N-Formyl-2-(5-nitrothiophen-2-yl)benzothiazole-6-carbohydrazide as a potential anti-tumour agent for prostate cancer in experimental studies. J Pharm Pharmacol 2013;65:411–22.
  • Rao NS, Nagesh N, Nayak LV, et al. Design and synthesis of DNA-intercalative naphthalimide- benzothiazole/cinnamide derivatives: cytotoxicity evaluation and topoisomerase-IIα inhibition. Med Chem Comm 2019;10:72–9.
  • Rao SVA, Rao BB, Sunkari S, et al. 2-Arylaminobenzothiazole-arylpropenone conjugates as tubulin polymerization inhibitors. Med Chem Commun 2017;8:924–41.
  • Osmaniye D, Levent S, Ardıc MC, et al. Synthesis and anticancer activity of some novel benzothiazolethiazolidine derivatives. Phosphorus Sulfur 2018;193:249–56.
  • Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nature Rev Drug Discov 2008;7:168–81.
  • Supuran CT. Structure and function of carbonic anhydrases. Biochem J 2016;473:2023–32.
  • Supuran CT. How many carbonic anhydrase inhibition mechanisms exist? J Enzyme Inhib Med Chem 2016;31:345–60.
  • Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011;10:767–77.
  • Supuran CT. Carbonic anhydrases and metabolism. Metabolites 2018;8:pii:E25.
  • Supuran CT. Carbonic anhydrase inhibition and the management of hypoxic tumors. Metabolites 2017;7:pii:E48.
  • Supuran CT. Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin Drug Discov 2017;12:61–88.
  • Supuran CT. Carbonic anhydrase inhibitors and their potential in a range of therapeutic areas. Expert Opin Ther Pat 2018;28:709–12.
  • Supuran CT. Applications of carbonic anhydrases inhibitors in renal and central nervous system diseases. Expert Opin Ther Pat 2018;28:713–21.
  • Nocentini A, Supuran CT. Advances in the structural annotation of human carbonic anhydrases and impact on future drug discovery. Expert Opin Drug Discov 2019;14:1175–97.
  • De Simone G, Supuran CT. (In)organic anions as carbonic anhydrase inhibitors. J Inorg Biochem 2012;111:117–29.
  • Supuran CT. Carbonic anhydrase inhibitors as emerging agents for the treatment and imaging of hypoxic tumors. Expert Opin Investig Drugs 2018;27:963–70.
  • Tars K, Vullo D, Kazaks A, et al. Sulfocoumarins (1,2-benzoxathiine 2,2-dioxides): a class of potent and isoform-selective inhibitors of tumor-associated carbonic anhydrases. J Med Chem 2013;56:293–300.
  • Köhler K, Hillebrecht A, Schulze Wischeler J, et al. Saccharin inhibits carbonic anhydrases: possible explanation for its unpleasant metallic aftertaste. Angew Chem Int Ed Engl 2007;46:7697–9.
  • Supuran CT, Ilies MA, Scozzafava A. Carbonic anhydrase inhibitors. Part 29. Interaction of isozymes I, II and IV with benzolamide-like derivatives. Eur J Med Chem 1998;33:739–52.
  • Sentürk M, Gülçin I, Daştan A, et al. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009;17:3207–11.
  • Nocentini A, Supuran CT. Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008–2018). Expert Opin Ther Pat 2018;28:729–40.
  • Di Fiore A, Pedone C, Antel J, et al. Carbonic anhydrase inhibitors: the X-ray crystal structure of ethoxzolamide complexed to human isoform II reveals the importance of thr200 and gln92 for obtaining tight-binding inhibitors. Bioorg Med Chem Lett 2008;18:2669–74.
  • SitaRam CM, Khloya P, et al. 4-Functionalized 1,3-diarylpyrazoles bearing 6-aminosulfonylbenzothiazole moiety as potent inhibitors of carbonic anhydrase isoforms hCA I, II, IX and XII. Bioorg Med Chem 2014;22:6945–52.
  • Ibrahim DA, Lasheen DS, Zaky MY, et al. Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII. Bioorg Med Chem 2015;23:4989–99.
  • Küçükbay FZ, Buğday N, Küçükbay H, et al. Synthesis, characterization and carbonic anhydrase inhibitory activity of novel benzothiazole derivatives. J Enzyme Inhib Med Chem 2016;31:1221–5.
  • Petrou A, Geronikaki A, Terzi E, et al. Inhibition of carbonic anhydrase isoforms I, II, IX and XII with secondary sulfonamides incorporating benzothiazole scaffolds. J Enzyme Inhib Med Chem 2016;31:1306–11.
  • Payaz DÜ, Küçükbay FZ, Küçükbay H, et al. Synthesis carbonic anhydrase enzyme inhibition and antioxidant activity of novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine moieties. J Enzyme Inhib Med Chem 2019;34:343–9.
  • Ammazzalorso A, Carradori S, Angeli A, et al. Fibrate-based N-acylsulphonamides targeting carbonic anhydrases: synthesis, biochemical evaluation, and docking studies. J Enzyme Inhib Med Chem 2019;34:1051–61.
  • Abdoli M, Angeli A, Bozdag M, et al. Synthesis and carbonic anhydrase I, II, VII, and IX inhibition studies with a series of benzo[d]thiazole-5- and 6-sulfonamides. J Enzyme Inhib Med Chem 2017;32:1071–8.
  • Alterio V, Esposito D, Monti SM, et al. Crystal structure of the human carbonic anhydrase II adduct with 1-(4-sulfamoylphenyl-ethyl)-2,4,6-triphenylpyridinium perchlorate, a membrane-impermeant, isoform selective inhibitor. J Enzyme Inhib Med Chem 2018;33:151–7.
  • Supuran CT. Carbon-versus sulphur-based zinc binding groups for carbonic anhydrase inhibitors? J Enzyme Inhib Med Chem 2018;33:485–95.
  • Pustenko A, Stepanovs D, Žalubovskis R, et al. 3H-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors. J Enzyme Inhib Med Chem 2017;32:767–75.
  • Ramya PVS, Angapelly S, Angeli A, et al. Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors. J Enzyme Inhib Med Chem 2017;32:1274–81.
  • Akocak S, Lolak N, Bua S, Supuran CT. Discovery of novel 1,3-diaryltriazene sulfonamides as carbonic anhydrase I, II, VII, and IX inhibitors. J Enzyme Inhib Med Chem 2018;33:1575–80.
  • El-Gazzar MG, Nafie NH, Nocentini A, et al. Carbonic anhydrase inhibition with a series of novel benzenesulfonamide-triazole conjugates. J Enzyme Inhib Med Chem 2018;33:1565–74.
  • D'Ascenzio M, Guglielmi P, Carradori S, et al. Open saccharin-based secondary sulfonamides as potent and selective inhibitors of cancer-related carbonic anhydrase IX and XII isoforms. J Enzyme Inhib Med Chem 2017;32:51–9.
  • Scozzafava A, Menabuoni L, Mincione F, et al. Carbonic anhydrase inhibitors: perfluoroalkyl/aryl-substituted derivatives of aromatic/heterocyclic sulfonamides as topical intraocular pressure-lowering agents with prolonged duration of action. J Med Chem 2000;43:4542–51.
  • Scozzafava A, Briganti F, Mincione G, et al. Carbonic anhydrase inhibitors: synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J Med Chem 1999;42:3690–700.
  • Supuran CT, Clare BW. Carbonic anhydrase inhibitors. Part 57. Quantum chemical QSAR of a group of 1,3,4-thiadiazole and 1,3,4-thiadiazoline disulfonamides with carbonic anhydrase inhibitory properties. Eur J Med Chem 1999;34:41–50.
  • Supuran CT, Nicolae A, Popescu A. Carbonic anhydrase inhibitors. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: the first inhibitors with equally high affinity towards cytosolic and membrane-bound isozymes. Eur J Med Chem 1996;31:431–8.
  • Sarikaya SBÖ, Topal F, Şentürk M, et al. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259–62.