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Mini-Reviews in Medicinal Chemistry

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ISSN (Online): 1875-5607

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Review Article

A Review on Anticancer Activities of Thiophene and Its Analogs

Author(s): Raghav Mishra*, Nitin Kumar, Isha Mishra and Neetu Sachan

Volume 20, Issue 19, 2020

Page: [1944 - 1965] Pages: 22

DOI: 10.2174/1389557520666200715104555

Price: $65

Abstract

Cancer is the world's second-largest cause of mortality and one of the biggest global health concerns. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Thiophene and its derivatives have surged as an influential scaffold, which, because of their appreciable diversity in biological activities, has drawn the concerned interest of the researchers in the field of medicinal chemistry. By the affluent introduction of its derivatives, which have antioxidant, anti-inflammatory, antimicrobial, and anticancer activities, the adaptability of the thiophene moiety has been displayed. The nature and positioning of the substitutions significantly impacted thiophene moiety activity. This decent array in the living response account about this moiety has picked plentiful researcher’s consideration to inquire about it to its peculiar potential across certain activities. In the field of cancer therapy against different cancer cells, the structure-activity relationship for each of the derivatives showed an excellent understanding of thiophene moiety. Information from the various articles revealed the key role of thiophene moiety and its derivatives to develop the vital lead compound. The essential anticancer mechanisms identified include inhibition of the topoisomerase, inhibition of tyrosine kinase, tubulin interaction and apoptosis induction through the activation of reactive oxygen species. This review is an endeavor to promote the anticancer potential of the derivatives, whether having thiophene or condensed thiophene as a core moiety or as a substituent that can lead in the future to synthesize varieties of chemotherapeutic entities in the field of cancer treatment.

Keywords: Thiophene, structure-activity relationship, anticancer activity, cell lines, antimicrobial, anti-inflammatory, antioxidant

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[1]
Bray, F.; Ferlay, J.; Soerjomataram, I.; Siegel, R.L.; Torre, L.A.; Jemal, A. Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J. Clin., 2018, 68(6), 394-424.
[http://dx.doi.org/10.3322/caac.21492] [PMID: 30207593]
[2]
Kumar, V.; Abbas, A.; Fausto, N.; Aster, J. Pathological basis of Disease, 8th ed; Saunders/Elsevier: Philadelphia, 2010.
[3]
Ferlay, J.; Soerjomataram, I.; Dikshit, R.; Eser, S.; Mathers, C.; Rebelo, M.; Parkin, D.M.; Forman, D.; Bray, F. Cancer incidence and mortality worldwide: Sources, methods and major patterns in GLOBOCAN 2012. Int. J. Cancer, 2015, 136(5), E359-E386.
[http://dx.doi.org/10.1002/ijc.29210] [PMID: 25220842]
[4]
Varmus, H. The new era in cancer research. Science, 2006, 312(5777), 1162-1165.
[http://dx.doi.org/10.1126/science.1126758] [PMID: 16728627]
[5]
Mishra, R.; Sachan, N.; Kumar, N.; Mishra, I.; Chand, P. Thiophene scaffold as prospective antimicrobial agent: A review. J. Heterocycl. Chem., 2018, 55(9), 2019-2034.
[http://dx.doi.org/10.1002/jhet.3249]
[6]
Dos Santos, F.A.; Pereira, M.C.; de Oliveira, T.B.; Mendonça Junior, F.J.B.; de Lima, M.D.C.A.; Pitta, M.G.D.R.; Pitta, I.D.R.; de Melo Rêgo, M.J.B.; da Rocha Pitta, M.G.; da Rocha, P.; Galdino, M. Anticancer properties of thiophene derivatives in breast cancer MCF-7 cells. Anticancer Drugs, 2017, 29(2), 157-166.
[PMID: 29256900]
[7]
de Jong, S.; Kooistra, A.J.; de Vries, E.G.; Mulder, N.H.; Zijlstra, J.G. Topoisomerase II as a target of VM-26 and 4′-(9-acridinylamino)methanesulfon-m-aniside in atypical multidrug resistant human small cell lung carcinoma cells. Cancer Res., 1993, 53(5), 1064-1071.
[PMID: 8382551]
[8]
Shah, R.; Verma, P.K. Synthesis of thiophene derivatives and their anti-microbial, antioxidant, anticorrosion and anticancer activity. BMC Chem., 2019, 13(1), 54.
[http://dx.doi.org/10.1186/s13065-019-0569-8] [PMID: 31384802]
[9]
Shafeeque, S.; Mohan, S.; Manjunatha, K.S. Synthesis, analgesic and antiinflammatory activity of some 2-substituted amino-3-(N p-tolyl carboxamido)-4,5-dimethyl thiophenes. Indian J. Heterocycl. Chem., 1999, 8(4), 297-300.
[10]
Kotaiah, Y.; Harikrishna, N.; Nagaraju, K.; Venkata Rao, C. Synthesis and antioxidant activity of 1,3,4-oxadiazole tagged thieno [2,3-d]pyrimidine derivatives. Eur. J. Med. Chem., 2012, 58, 340-345.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.007] [PMID: 23149297]
[11]
Wang, S.Q.; Fang, L.; Liu, X.; Zhao, K. Design, synthesis, and hypnotic activity of pyrazolo[1,5-a]pyrimidine derivatives. Chin. Chem. Lett., 2004, 15(8), 885-888.
[12]
Mishra, R.; Tomer, I.; Kumar, S. Synthesis and antimicrobial evaluation of novel thiophene derivatives. Pharm. Sin., 2012, 3, 332-336.
[13]
Ashalatha, B.V.; Narayana, B.; Vijaya Raj, K.K.; Suchetha Kumari, N. Synthesis of some new bioactive 3-amino-2-mercapto-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one derivatives. Eur. J. Med. Chem., 2007, 42(5), 719-728..
[http://dx.doi.org/10.1016/j.ejmech.2006.11.007] [PMID: 17189665]
[14]
Press, J.B.; Mcnally, J.J. Thiophene systems. 10. The synthesis and chemistry of some thienopyridinols. J. Heterocycl. Chem., 1988, 25(5), 1571-1581.
[http://dx.doi.org/10.1002/jhet.5570250559]
[15]
Duddukuri, N.K.; Thatikonda, S.; Godugu, C.; Kumar, R.A.; Doijad, N. Synthesis of novel thiophene‐chalcone derivatives as anticancer‐and apoptosis‐inducing agents. Chem. Select, 2018, 3(24), 6859-6864.
[http://dx.doi.org/10.1002/slct.201800613]
[16]
Liao, X.; Huang, J.; Lin, W.; Long, Z.; Xie, Y.; Ma, W. APTM, a thiophene heterocyclic compound, inhibits human colon cancer HCT116 cell proliferation through p53-dependent induction of apoptosis. DNA Cell Biol., 2018, 37(2), 70-77.
[http://dx.doi.org/10.1089/dna.2017.3962] [PMID: 29215922]
[17]
Malani, K.; Thakkar, S.S.; Thakur, M.C.; Ray, A.; Doshi, H. Synthesis, characterization and in silico designing of diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxylate derivative as anti-proliferative and anti-microbial agents. Bioorg. Chem., 2016, 68, 265-274.
[http://dx.doi.org/10.1016/j.bioorg.2016.09.001] [PMID: 27616159]
[18]
Cai, G.; Wang, S.; Zhao, L.; Sun, Y.; Yang, D.; Lee, R.J.; Zhao, M.; Zhang, H.; Zhou, Y. Thiophene derivatives as anticancer agents and their delivery to tumor cells using albumin nanoparticles. Molecules, 2019, 24(1), 192-206.
[http://dx.doi.org/10.3390/molecules24010192] [PMID: 30621360]
[19]
Gomha, S.M.; Edrees, M.M.; Altalbawy, F.M. Synthesis and characterization of some new bis-pyrazolyl-thiazoles incorporating the thiophene moiety as potent anti-tumor agents. Int. J. Mol. Sci., 2016, 17(9), 1499-1509.
[http://dx.doi.org/10.3390/ijms17091499] [PMID: 27618013]
[20]
Labib, M.B.; Lamie, P.F. Design, synthesis and biological evaluation of novel thiophene and theinopyrimidine derivatives as anticancer agents. Med. Chem. Res., 2016, 25(11), 2607-2618.
[http://dx.doi.org/10.1007/s00044-016-1703-y]
[21]
de Oliveira, J.F.; da Silva, A.L.; Vendramini-Costa, D.B.; da Cruz Amorim, C.A.; Campos, J.F.; Ribeiro, A.G.; Olímpio de Moura, R.; Neves, J.L.; Ruiz, A.L.; Ernesto de Carvalho, J. Alves de Lima, Mdo.C. Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities. Eur. J. Med. Chem., 2015, 104, 148-156.
[http://dx.doi.org/10.1016/j.ejmech.2015.09.036] [PMID: 26454648]
[22]
Ghorab, M.M.; Bashandy, M.S.; Alsaid, M.S. Novel thiophene derivatives with sulfonamide, isoxazole, benzothiazole, quinoline and anthracene moieties as potential anticancer agents. Acta Pharm., 2014, 64(4), 419-431.
[http://dx.doi.org/10.2478/acph-2014-0035] [PMID: 25531783]
[23]
Souza, B.C.; De Oliveira, T.B.; Aquino, T.M.; de Lima, M.C.; Pitta, I.R.; Galdino, S.L.; Lima, E.O.; Gonçalves-Silva, T.; Militão, G.C.; Scotti, L.; Scotti, M.T.; Mendonça, F.J. Jr Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis. Acta Pharm., 2012, 62(2), 221-236.
[http://dx.doi.org/10.2478/v10007-012-0017-y] [PMID: 22750820]
[24]
Jarak, I.; Kralj, M.; Piantanida, I.; Suman, L.; Zinić, M.; Pavelić, K.; Karminski-Zamola, G. Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno[3′,2′:4,5]thieno- and thieno[2′,3′:4,5] thieno [2,3-c]quinolones: synthesis, photochemical synthesis, DNA binding, and antitumor evaluation. Bioorg. Med. Chem., 2006, 14(8), 2859-2868.
[http://dx.doi.org/10.1016/j.bmc.2005.12.004] [PMID: 16412644]
[25]
Dallemagne, P.; Khanh, L.P.; Alsaïdi, A.; Varlet, I.; Collot, V.; Paillet, M.; Bureau, R.; Rault, S. Synthesis and biological evaluation of five-membered heterocycles fused to cyclopenta[c]thiophene as new antitumor agents. Bioorg. Med. Chem., 2003,11(7), 1161-1167..
[http://dx.doi.org/10.1016/S0968-0896(02)00654-5] [PMID: 12628643]
[26]
Shebl, M. Coordination behavior of new bis (tridentate ONO, ONS and ONN) donor hydrazones towards some transition metal ions: Synthesis, spectral, thermal, antimicrobial and antitumor studies. J. Mol. Struct., 2017, 1128, 79-93.
[http://dx.doi.org/10.1016/j.molstruc.2016.08.056]
[27]
of Aguiar.; A.C.V.; of Moura, R.O.; Junior, J.F.B.M.; de Oliveira Rocha, H.A.; Camara, R.B.G.; Schiavon, M.D.S.C. Evaluation of the antiproliferative activity of 2-amino thiophene derivatives against human cancer cells lines. Biomed. Pharmacother., 2016, 84, 403-414.
[http://dx.doi.org/10.1016/j.biopha.2016.09.026]
[28]
Romagnoli, R.; Baraldi, P.G.; Lopez-Cara, C.; Salvador, M.K.; Preti, D.; Tabrizi, M.A.; Balzarini, J.; Nussbaumer, P.; Bassetto, M.; Brancale, A.; Fu, X.H. Yang-Gao; Li, J.; Zhang, S.Z.; Hamel, E.; Bortolozzi, R.; Basso, G.; Viola, G. Design, synthesis and biological evaluation of 3,5-disubstituted 2-amino thiophene derivatives as a novel class of antitumor agents. Bioorg. Med. Chem., 2014, 22(18), 5097-5109.
[http://dx.doi.org/10.1016/j.bmc.2013.12.030] [PMID: 24398384]
[29]
Samir, E.M.; Abouzied, A.S.; Hamed, F.I. The synthesis and cytotoxicity of novel thiophene derivatives derived from 2-(4-oxo-4, 4-dihydrothiazol-2-yl) acetonitrile. Int. J. Org. Chem. (Irvine), 2016, 6(2), 85-94.
[http://dx.doi.org/10.4236/ijoc.2016.62009]
[30]
Gouda, M.A.; Eldien, H.F.; Girges, M.M.; Berghot, M.A. Synthesis and antitumor evaluation of thiophene based azo dyes incorporating pyrazolone moiety. J. Saudi Chem. Soc., 2016, 20(2), 151-157.
[http://dx.doi.org/10.1016/j.jscs.2012.06.004]
[31]
Do, C.V.; Faouzi, A.; Barette, C.; Farce, A.; Fauvarque, M.O.; Colomb, E.; Catry, L.; Berthier-Vergnes, O.; Haftek, M.; Barret, R.; Lomberget, T. Synthesis and biological evaluation of thiophene and benzo[b]thiophene analogs of combretastatin A-4 and isocombretastatin A-4: A comparison between the linkage positions of the 3,4,5-trimethoxystyrene unit. Bioorg. Med. Chem. Lett., 2016, 26(1), 174-180.
[http://dx.doi.org/10.1016/j.bmcl.2015.11.010] [PMID: 26602281]
[32]
Ghorab, M.M.; Alsaid, M.S.; Al-Dosari, M.S.; Ragab, F.A.; Al-Mishari, A.A.; Almoqbil, A.N. Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents. Acta Pharm., 2016, 66(2), 155-171.
[http://dx.doi.org/10.1515/acph-2016-0016] [PMID: 27279061]
[33]
Appalanaidu, K.; Kotcherlakota, R.; Dadmal, T.L.; Bollu, V.S.; Kumbhare, R.M.; Patra, C.R. Synthesis and biological evaluation of novel 2-imino-4-thiazolidinone derivatives as potent anti-cancer agents. Bioorg. Med. Chem. Lett., 2016, 26(21), 5361-5368.
[http://dx.doi.org/10.1016/j.bmcl.2016.08.013] [PMID: 27546293]
[34]
Zhang, B.; Li, Y.H.; Liu, Y.; Chen, Y.R.; Pan, E.S.; You, W.W.; Zhao, P.L. Design, synthesis and biological evaluation of novel 1,2,4-triazolo [3,4-b][1,3,4] thiadiazines bearing furan and thiophene nucleus. Eur. J. Med. Chem., 2015, 103, 335-342.
[http://dx.doi.org/10.1016/j.ejmech.2015.08.053] [PMID: 26363869]
[35]
Sztanke, M.; Rzymowska, J.; Sztanke, K. Synthesis, structure elucidation and identification of antiproliferative activities of a novel class of thiophene bioisosteres bearing the privileged 7,8-dihydroimidazo[2,1-c][1,2,4]triazin-4(6H)-one scaffold. Bioorg. Med. Chem., 2015, 23(13), 3448-3456.
[http://dx.doi.org/10.1016/j.bmc.2015.04.037] [PMID: 25975637]
[36]
Ghorab, M.M.; El-Gazzar, M.G.; Alsaid, M.S. Design and synthesis of novel thiophenes bearing biologically active aniline, aminopyridine, benzylamine, nicotinamide, pyrimidine and triazolopyrimidine moieties searching for cytotoxic agents. Acta Pol. Pharm., 2014, 71(3), 401-407.
[PMID: 25265819]
[37]
Alsaid, M.S.; El-Gazzar, M.G.; Ghorab, M.M. Anticancer activity of novel thiophenes containing a biological active diphenylsulfone, diazepin, piperidine, oxazepine, acryladehyde and sulfonamide moieties. Drug Res. (Stuttg.), 2013, 63(5), 263-269.
[http://dx.doi.org/10.1055/s-0033-1337928] [PMID: 23529721]
[38]
Romagnoli, R.; Baraldi, P.G.; Cruz-Lopez, O.; Tolomeo, M.; Di Cristina, A.; Pipitone, R.M.; Grimaudo, S.; Balzarini, J.; Brancale, A.; Hamel, E. Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives. Bioorg. Med. Chem. Lett., 2011, 21(9), 2746-2751.
[http://dx.doi.org/10.1016/j.bmcl.2010.11.083] [PMID: 21146985]
[39]
Shams, H.Z.; Mohareb, R.M.; Helal, M.H.; Mahmoud, A.E. Novel synthesis and antitumor evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. Molecules, 2010, 16(1), 52-73.
[http://dx.doi.org/10.3390/molecules16010052] [PMID: 21187817]
[40]
Mohareb, R.M.; Fahmy, A.A. Cytotoxicity of novel 4,5,6,7-tetrahydrobenzo[b]thiophene derivatives towards human tumor and normal cell lines and their uses as anti-leishmanial agents. Eur. Chem. Bull., 2013, 2(8), 545-553.
[41]
Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Cara, C.L.; Cruz-Lopez, O.; Preti, D.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Zonta, N.; Balzarini, J.; Brancale, A.; Sarkar, T.; Hamel, E. Design, synthesis, and biological evaluation of thiophene analogues of chalcones. Bioorg. Med. Chem., 2008, 16(10), 5367-5376.
[http://dx.doi.org/10.1016/j.bmc.2008.04.026] [PMID: 18440234]
[42]
Krishnamurthy, M.; Gurley, S.; Moore, B.M. II Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs. Bioorg. Med. Chem., 2008, 16(13), 6489-6500.
[http://dx.doi.org/10.1016/j.bmc.2008.05.034] [PMID: 18524604]
[43]
Diana, P.; Carbone, A.; Barraja, P.; Montalbano, A.; Martorana, A.; Dattolo, G.; Gia, O.; Dalla Via, L.; Cirrincione, G. Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: Analogues of marine alkaloid nortopsentin. Bioorg. Med. Chem. Lett., 2007, 17(8), 2342-2346.
[http://dx.doi.org/10.1016/j.bmcl.2007.01.065] [PMID: 17306531]
[44]
Al-Huniti, M.H.; El-Abadelah, M.M.; Zahra, J.A.; Sabri, S.S.; Ingendoh, A. Facile synthesis of some novel pyrido[3′,2′:4,5] thieno[2,3-b][1,4]thiazine-8-carboxylic acids. Molecules, 2007, 12(3), 497-503.
[http://dx.doi.org/10.3390/12030497] [PMID: 17851406]
[45]
Raju, S.; Batchu, V.R.; Swamy, N.K.; Dev, R.V.; Sreekanth, B.R.; Babu, J.M.; Vyas, K.; Kumar, P.R.; Mukkanti, K.; Annamalai, P.; Pal, M. Tandem versus single C–C bond forming reaction under palladium–copper catalysis: Regioselective synthesis of α-pyrones fused with thiophene. Tetrahedron, 2006, 62(41), 9554-9570.
[http://dx.doi.org/10.1016/j.tet.2006.07.095]
[46]
Flynn, B.L.; Flynn, G.P.; Hamel, E.; Jung, M.K. The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. Bioorg. Med. Chem. Lett., 2001, 11(17), 2341-2343..
[http://dx.doi.org/10.1016/S0960-894X(01)00436-X] [PMID: 11527727]
[47]
Xu, W.C.; Zhou, Q.; Ashendel, C.L.; Chang, C.T.; Chang, C.J. Novel protein kinase C inhibitors: synthesis and PKC inhibition of β-substituted polythiophene derivatives., Bioorg. Med. Chem. Lett., 1999, 9(15), 2279-2282..
[http://dx.doi.org/10.1016/S0960-894X(99)00375-3] [PMID: 10465561]
[48]
Othman, D.I.A.; Selim, K.B.; El-Sayed, M.A.; Tantawy, A.S.; Amen, Y.; Shimizu, K.; Okauchi, T.; Kitamura, M. Design, synthesis and anticancer evaluation of new substituted thiophene-quinoline derivatives. Bioorg. Med. Chem., 2019, 27(19)115026
[http://dx.doi.org/10.1016/j.bmc.2019.07.042] [PMID: 31416740]
[49]
Zhao, M.; Cui, Y.; Zhao, L.; Zhu, T.; Lee, R.J.; Liao, W.; Sun, F.; Li, Y.; Teng, L. Thiophene derivatives as new anticancer agents and their therapeutic delivery using folate receptor-targeting nanocarriers. ACS Omega, 2019, 4(5), 8874-8880.
[http://dx.doi.org/10.1021/acsomega.9b00554] [PMID: 31459975]
[50]
Ghorafi, M.A.H.; Kamal, A.M.; Abdullah, J.H. Yahya1, T.A.A.; Yassin, S.H. Synthesis and evaluation of anticancer activity of some new schiff bases of amino-thiophene derivatives. Eur. J. Pharm. Med. Res., 2020, 7(1), 111-115.
[51]
Zhao, F.; Sun, X.; Lu, W.; Xu, L.; Shi, J.; Yang, S.; Zhou, M.; Su, F.; Lin, F.; Cao, F. Synthesis of novel, DNA binding heterocyclic dehydroabietylamine derivatives as potential antiproliferative and apoptosis-inducing agents. Drug Deliv., 2020, 27(1), 216-227. .
[http://dx.doi.org/10.1080/10717544.2020.1716879] [PMID: 31984809]
[52]
Lisboa, T.; Silva, D.; Duarte, S.; Ferreira, R.; Andrade, C.; Lopes, A.L.; Ribeiro, J.; Farias, D.; Moura, R.; Reis, M.; Medeiros, K.; Magalhães, H.; Sobral, M. Toxicity and antitumor activity of a thiophene-acridine hybrid. Molecules, 2019, 25(1), 1-12.
[http://dx.doi.org/10.3390/molecules25010064] [PMID: 31878135]
[53]
Romagnoli, R.; Baraldi, P.G.; Cara, C.L.; Hamel, E.; Basso, G.; Bortolozzi, R.; Viola, G. Synthesis and biological evaluation of 2- (3′,4′,5′-trimethoxybenzoyl)-3-aryl/arylaminobenzo[b]thiophene derivatives as a novel class of antiproliferative agents. Eur. J. Med. Chem., 2010, 45(12), 5781-5791..
[http://dx.doi.org/10.1016/j.ejmech.2010.09.038] [PMID: 20933308]
[54]
Romagnoli, R.; Baraldi, P.G.; Carrion, M.D.; Cruz-Lopez, O.; Tolomeo, M.; Grimaudo, S.; Di Cristina, A.; Pipitone, M.R.; Balzarini, J.; Brancale, A.; Hamel, E. Substituted 2-(3′,4′,5′-trimethoxybenzoyl)-benzo[b]thiophene derivatives as potent tubulin polymerization inhibitors. Bioorg. Med. Chem., 2010, 18(14), 5114-5122.
[http://dx.doi.org/10.1016/j.bmc.2010.05.068] [PMID: 20579891]
[55]
Penthala, N.R.; Sonar, V.N.; Horn, J.; Leggas, M.; Yadlapalli, J.S.K.; Crooks, P.A. Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents. MedChemComm, 2013, 4(7), 1073-1078.
[http://dx.doi.org/10.1039/c3md00130j] [PMID: 23956835]
[56]
Wu, X.; Li, M.; Qu, Y.; Tang, W.; Zheng, Y.; Lian, J.; Ji, M.; Xu, L. Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity. Bioorg. Med. Chem., 2010, 18(11), 3812-3822.
[http://dx.doi.org/10.1016/j.bmc.2010.04.046] [PMID: 20466555]
[57]
Matsunaga, N.; Kaku, T.; Itoh, F.; Tanaka, T.; Hara, T.; Miki, H.; Iwasaki, M.; Aono, T.; Yamaoka, M.; Kusaka, M.; Tasaka, A. C17,20-lyase inhibitors I. Structure-based de novo design and SAR study of C17,20-lyase inhibitors. Bioorg. Med. Chem., 2004, 12(9), 2251-2273.
[http://dx.doi.org/10.1016/j.bmc.2004.02.007] [PMID: 15080924]
[58]
El-Sharkawy, K.A.; Said, M.M.; Dardas, G. Synthesis and antitumor activity of some fused heterocyclic compounds based on cyclohepta [b] thiophene derivatives. Izv. Him., 2014, 46(4), 691-699.
[59]
Albratty, M.; El-Sharkawy, K.A.; Alam, S. Original research paper. Synthesis and antitumor activity of some novel thiophene, pyrimidine, coumarin, pyrazole and pyridine derivatives. Acta Pharm., 2017, 67(1), 15-33.
[http://dx.doi.org/10.1515/acph-2017-0004] [PMID: 28231053]
[60]
Ghorab, M.M.; Alsaid, M.S. Anticancer activity of some novel thieno [2,3-d] pyrimidine derivatives. Biomed. Res., 2016, 27(1), 110-115.
[61]
Mavrova, A.T.; Dimov, S.; Yancheva, D.; Rangelov, M.; Wesselinova, D.; Tsenov, J.A. Synthesis, anticancer activity and photostability of novel 3-ethyl-2-mercapto-thieno[2,3-d]pyrimidin-4(3H)-ones. Eur. J. Med. Chem., 2016, 123, 69-79.
[http://dx.doi.org/10.1016/j.ejmech.2016.07.022] [PMID: 27474924]
[62]
Mohareb, R.M.; Wardakhan, W.W.; Hamed, F.I. Synthesis and cytotoxicity of fused thiophene and pyrazole derivatives derived from 2-N-acetyl-3-cyano-4, 5, 6, 7-tetrahydrobenzo [b] thiophene. Med. Chem. Res., 2015, 24(5), 2043-2054.
[http://dx.doi.org/10.1007/s00044-014-1273-9]
[63]
Pavase, L.S.; Mane, D.V. Synthesis and anticancer activities of novel (tetrahydrobenzo [4,5] thieno [2,3-d] pyrimidine-4-yl)-pyrolidine-2-carboxylic acid derivatives. Med. Chem. Res., 2016, 25(10), 2380-2391.
[http://dx.doi.org/10.1007/s00044-016-1692-x]
[64]
Romagnoli, R.; Baraldi, P.G.; Kimatrai Salvador, M.; Preti, D.; Aghazadeh Tabrizi, M.; Bassetto, M.; Brancale, A.; Hamel, E.; Castagliuolo, I.; Bortolozzi, R.; Basso, G.; Viola, G. Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b] thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents. J. Med. Chem., 2013, 56(6), 2606-2618.
[http://dx.doi.org/10.1021/jm400043d] [PMID: 23445496]
[65]
Sivasubramanian, N.; Reddy, M.V.; Aravinda, M.; Sravanthi, R.; Sirisha, S. Synthesis, characterization, anti-microbial and anti-cancer activity of novel heterocyclic system containing bridgehead nitrogen atom. Chem. Sci. Trans., 2012, 1(2), 401-409.
[http://dx.doi.org/10.7598/cst2012.175]
[66]
Cao, X.; Li, H.; Chen, C.; Xu, S. Synthesis and Bioevaluation of thieno[2,3-d]pyrimidinone derivatives as potential tumor cell growth inhibitors. J. Chem., 2013, 2013, 1-13.
[67]
Hayakawa, M.; Kaizawa, H.; Moritomo, H.; Koizumi, T.; Ohishi, T.; Okada, M.; Ohta, M.; Tsukamoto, S.; Parker, P.; Workman, P.; Waterfield, M. Synthesis and biological evaluation of 4-morpholino-2-phenylquinazolines and related derivatives as novel PI3 kinase p110α inhibitors. Bioorg. Med. Chem., 2006, 14(20), 6847-6858.
[http://dx.doi.org/10.1016/j.bmc.2006.06.046] [PMID: 16837202]
[68]
Pédeboscq, S.; Gravier, D.; Casadebaig, F.; Hou, G.; Gissot, A.; De Giorgi, F.; Ichas, F.; Cambar, J.; Pometan, J.P. Synthesis and study of antiproliferative activity of novel thienopyrimidines on glioblastoma cells. Eur. J. Med. Chem., 2010, 45(6), 2473-2479.
[http://dx.doi.org/10.1016/j.ejmech.2010.02.032] [PMID: 20219270]
[69]
Katada, J.; Iijima, K.; Muramatsu, M.; Takami, M.; Yasuda, E.; Hayashi, M.; Hattori, M.; Hayashi, Y. Cytotoxic effects of NSL- 1406, a new thienopyrimidine derivative, on leukocytes and osteoclasts. Bioorg. Med. Chem. Lett., 1999, 9(6), 797-802..
[http://dx.doi.org/10.1016/S0960-894X(99)00088-8] [PMID: 10206538]
[70]
Hassan, A.Y.; Husseiny, E.M. Synthesis and Anticancer Evaluation of some novel thiophene, thieno [3,2‐d] pyrimidine, thieno [3,2‐b] pyridine, and thieno [3,2‐e][1,4] oxazepine derivatives containing benzothiazole moiety. J. Heterocycl. Chem., 2019, 56(9), 2419-2429.
[http://dx.doi.org/10.1002/jhet.3629]
[71]
Waterson, A.G.; Petrov, K.G.; Hornberger, K.R.; Hubbard, R.D.; Sammond, D.M.; Smith, S.C.; Dickson, H.D.; Caferro, T.R.; Hinkle, K.W.; Stevens, K.L.; Dickerson, S.H.; Rusnak, D.W.; Spehar, G.M.; Wood, E.R.; Griffin, R.J.; Uehling, D.E. Synthesis and evaluation of aniline headgroups for alkynyl thienopyrimidine dual EGFR/ErbB-2 kinase inhibitors. Bioorg. Med. Chem. Lett., 2009, 19(5), 1332-1336.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.080] [PMID: 19208477]
[72]
Chao, Y.H.; Kuo, S.C.; Ku, K.; Chiu, I.P.; Wu, C.H.; Mauger, A.; Wang, H.K.; Lee, K.H. .Synthesis and cytotoxicity of methyl-4,8- dihydrobenzo[1,2-b:5,4-b′]dithiophene-4,8-dione derivatives. Bioorg.Med. Chem., 1999, 7(6), 1025-1031..
[http://dx.doi.org/10.1016/S0968-0896(98)00241-7] [PMID: 10428370]
[73]
Abdou, W.M.; Ganoub, N.A.; Sabry, E. Spiro-and substituted tetrahydrobenzo [b] thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies. Monatsh. Chem., 2016, 147(3), 619-626.
[http://dx.doi.org/10.1007/s00706-015-1542-4]
[74]
Zhang, W.; Ma, T.; Li, S.; Yang, Y.; Guo, J.; Yu, W.; Kong, L. Antagonizing STAT3 activation with benzo[b]thiophene 1, 1-dioxide based small molecules. Eur. J. Med. Chem., 2017, 125, 538-550.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.068] [PMID: 27718470]
[75]
Qu, S.; Mulamoottil, V.A.; Nayak, A.; Ryu, S.; Hou, X.; Song, J.; Yu, J.; Sahu, P.K.; Zhao, L.X.; Choi, S.; Lee, S.K.; Jeong, L.S. Design, synthesis, and anticancer activity of C8-substituted-4′-thionucleosides as potential HSP90 inhibitors. Bioorg. Med. Chem., 2016, 24(16), 3418-3428.
[http://dx.doi.org/10.1016/j.bmc.2016.05.041] [PMID: 27283788]
[76]
Said, M.; Elshihawy, H. Synthesis, anticancer activity and structure-activity relationship of some anticancer agents based on cyclopenta (b) thiophene scaffold. Pak. J. Pharm. Sci., 2014, 27(4), 885-892.
[PMID: 25015456]

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