Design, synthesis and cytotoxic activity of certain novel chalcone analogous compounds

Simple item page
dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorEl-Meligie S.
dc.contributor.authorTaher A.T.
dc.contributor.authorKamal A.M.
dc.contributor.authorYoussef A.
dc.contributor.otherPharmaceutical Organic Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherCairo University
dc.contributor.otherCairo
dc.contributor.other11561
dc.contributor.otherEgypt; Pharmaceutical Organic Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University for Modern Sciences and Arts (MSA)
dc.contributor.otherGiza
dc.contributor.otherEgypt; Pharmaceutical Organic Chemistry Department
dc.contributor.otherFaculty of Pharmacy and Drug Manufacturing
dc.contributor.otherMisr University for Science and Technology
dc.contributor.otherGiza
dc.contributor.otherEgypt
dc.date.accessioned2020-01-09T20:41:28Z
dc.date.available2020-01-09T20:41:28Z
dc.date.issued2017
dc.descriptionScopus
dc.description.abstractA series of chalcone analogous compounds were designed and synthesized. Replacing/substituting the enone or ethylenic bridge of the parent chalcone with rigid heterocyclic moieties or substituted aromatic amines gave nineteen target compounds. Their cytotoxic activities were screened against both breast and liver cancer cells as well as breast and liver normal cells. Target compounds were also evaluated for their inhibition activity of tubulin beta polymerization. Target compound 2e, 3a, 3b, 3c, 4a-4d, 5a, 5b and 6 showed broad spectrum excellent anticancer activity against both MCF-7 and HepG2. Compound 4a showed the most TUBb inhibition activity. � 2016 Elsevier Masson SASen_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=17464&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.1016/j.ejmech.2016.09.099
dc.identifier.doiPubMed ID 27744186
dc.identifier.issn2235234
dc.identifier.otherhttps://doi.org/10.1016/j.ejmech.2016.09.099
dc.identifier.otherPubMed ID 27744186
dc.identifier.urihttps://t.ly/LXv1g
dc.language.isoEnglishen_US
dc.publisherElsevier Masson SASen_US
dc.relation.ispartofseriesEuropean Journal of Medicinal Chemistry
dc.relation.ispartofseries126
dc.subjectCancer cell linesen_US
dc.subjectChalcone derivativesen_US
dc.subjectCytotoxic activityen_US
dc.subjectNormal cell linesen_US
dc.subjectReplacing enone bridgeen_US
dc.subjectTubulin beta polymerization inhibitorsen_US
dc.subject3 (4 bromophenyl) 3 [(3 chloro 4 fluorophenyl)amino] 2 hydroxy 1 (3 methoxyphenyl)propan 1 oneen_US
dc.subject4 (4 bromophenyl) 6 (3 methoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 bromophenyl) 6 (3,4,5 trimethoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 bromophenyl) 6 (4 methoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 chlorophenyl) 6 (3 methoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 chlorophenyl) 6 (3,4,5 trimethoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 flurophenyl) 6 (3,4,5 trimethoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject4 (4 mehoxyphenyl) 6 (3,4,5 trimethoxyphenyl) 3,4 dihydropyrimidine 2(1h) thioneen_US
dc.subject45 (4 chlorophenyl) 3 (3 methoxyphenyl) 4,5 dihydro 1h pyrazol 4 olen_US
dc.subject5 (4 bromophenyl) 3 (3 methoxyphenyl) 1 phenyl 4,5 dihydro 1h pyrazol 4 olen_US
dc.subject5 (4 bromophenyl) 3 (3 methoxyphenyl) 4,5 dihydro 1h pyrazol 4 olen_US
dc.subject5 (4 chlorophenyl) 3 (3 methoxyphenyl) 1 phenyl 4,5 dihydro 1h pyrazol 4 olen_US
dc.subject5 (4 flurophenyl) 3 (4 methoxyphenyl) 1 phenyl 4,5 dihydro 1h pyrazol 4 olen_US
dc.subject5 (4 methoxyphenyl) 3 (4 methoxyphenyl) 1 phenyl 4,5 dihydro 1h pyrazol 4 olen_US
dc.subjectantimitotic agenten_US
dc.subjectbeta tubulinen_US
dc.subjectchalcone derivativeen_US
dc.subjectcolchicineen_US
dc.subjectcytotoxic agenten_US
dc.subjectprotein inhibitoren_US
dc.subjectunclassified drugen_US
dc.subject[3 (4 bromophenyl)oxiran 2 yl](3 methoxyphenyl)methanoneen_US
dc.subject[3 (4 bromophenyl)thiiran 2 yl](3 methoxyphenyl)methanoneen_US
dc.subject[3 (4 chlorophenyl)oxiran 2 yl](3 methoxyphenyl)methanoneen_US
dc.subject[3 (4 chlorophenyl)thiiran 2 yl](3 methoxyphenyl)methanoneen_US
dc.subject[3 (4 flurophenyl)oxiran 2 yl](4 methoxyphenyl)methanoneen_US
dc.subjectantineoplastic agenten_US
dc.subjectchalconeen_US
dc.subjecttubulinen_US
dc.subjecttubulin modulatoren_US
dc.subjectantiproliferative activityen_US
dc.subjectArticleen_US
dc.subjectcancer inhibitionen_US
dc.subjectcomparative studyen_US
dc.subjectconcentration responseen_US
dc.subjectcontrolled studyen_US
dc.subjectcytotoxicityen_US
dc.subjectdrug cytotoxicityen_US
dc.subjectdrug designen_US
dc.subjectdrug potencyen_US
dc.subjectdrug synthesisen_US
dc.subjectHepG2 cell lineen_US
dc.subjecthumanen_US
dc.subjecthuman cellen_US
dc.subjectMCF 7 cell lineen_US
dc.subjectmicrotubule assemblyen_US
dc.subjectprotein polymerizationen_US
dc.subjectbreasten_US
dc.subjectcell proliferationen_US
dc.subjectchemistryen_US
dc.subjectcytologyen_US
dc.subjectdrug effectsen_US
dc.subjectHep-G2 cell lineen_US
dc.subjectliveren_US
dc.subjectMCF-7 cell lineen_US
dc.subjectsynthesisen_US
dc.subjectAntineoplastic Agentsen_US
dc.subjectBreasten_US
dc.subjectCell Proliferationen_US
dc.subjectChalconeen_US
dc.subjectChemistry Techniques, Syntheticen_US
dc.subjectDrug Designen_US
dc.subjectHep G2 Cellsen_US
dc.subjectHumansen_US
dc.subjectLiveren_US
dc.subjectMCF-7 Cellsen_US
dc.subjectTubulinen_US
dc.subjectTubulin Modulatorsen_US
dc.titleDesign, synthesis and cytotoxic activity of certain novel chalcone analogous compoundsen_US
dc.typeArticleen_US
dcterms.isReferencedByNepali, K., Sharma, S., Sharma, M., Bedi, P.M.S., Dhar, K.L., Rational approaches, design strategies, structure activity relationship and mechanistic insights for anticancer hybrids (2014) Eur. Med. Chem., 77, pp. 422-487; Petrelli, A., Giordano, S., From single- to multi-target drugs in cancer therapy: when a specificity becomes an advantage (2008) Curr. Med. Chem., 15, pp. 422-432; De Martino, G., Edler, M.C., La Regina, G., Coluccia, A., Barbera, M.C., Barrow, D., Nicholson, R.I., Silvestri, R., New Arylthioindoles: potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies (2006) J. Med. Chem., 49, pp. 947-954; Flynn, B.L., Gill, G.S., Grobelny, D.W., Chaplin, J.H., Paul, D., Leske, A.F., Lavranos, T.C., Kremmidiotis, G., Discovery of 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a tubulin polymerization inhibitor with potent antiproliferative and tumor vascular disrupting properties (2011) J. Med. Chem., 54, pp. 6014-6027; Zhang, X., Kong, Y., Zhang, J., Su, M., Zhou, Y., Zang, Y., Li, J., Lu, W., Design, synthesis and biological evaluation of colchicine derivatives as novel tubulin and histone deacetylase dual inhibitors (2015) Eur. Med. Chem., 95, pp. 127-135; Botta, M., Forli, S., Magnani, M., Manetti, F., Molecular modeling approaches to study the binding mode on tubulin of microtubule destabilizing and stabilizing agents (2009) Top. Curr. Chem., 286, pp. 279-328; Shen, Y.-N., Lin, L., Qiu, H.-Y., Zou, W.-Y., Qian, Y., Zhu, H.-L., The design, synthesis, in vitro biological evaluation and molecular modeling of novel benzenesulfonate derivatives bearing chalcone moieties as potent anti-microtubulin polymerization agents (2015) RSC Adv., 5, pp. 23767-23777; Ranjit, P.M., Abdul-Rahman, S., Kumar, K.P., Prasad, Y.R., Santhipriya, T., Manikanta, G.C.V.S., Sudeepthi, N.L., Synthesis, screening and in vitro anticancer activity of piperazine nucleus containing novel chalcones on different cell lines (2013) Int. J. Pharma. Tech., 5, pp. 284-293; Syam, S., Abdelwahab, S.I., Al-Mamary, M.A., Mohan, S., Synthesis of chalcones with anticancer activities (2012) Molecules, 17, pp. 6179-6195; Dyrager, C., Wickstr�m, M., Frid�n-Saxin, M., Friberg, A., Dahl�n, K., Wall�n, E.A.A., Gullbo, J., Luthman, K., Inhibitors and promoters of tubulin polymerization: synthesis and biological evaluation of chalcones and related dienones as potential anticancer agents (2011) Bioorg. Med. Chem., 19, pp. 2659-2665; Shan, Y., Zhang, J., Liu, J., Wang, M., Dong, Y., Development of combretastatin A-4 derivatives as anticancer agents (2011) Curr. Med. Chem., 18, pp. 523-538; Han, H., Zhao, Y., Cuthbertson, T., Hartman, R.F., Rose, S.D., Cell cycle arrest and apoptosis induction by an anticancer chalcone epoxide (2010) Arch. Pharm. Chem. Life Sci., 8, pp. 429-439. , [ref importance of pyrazole moiety] D. Pal, S. Saha, S. Singh, Importance of Pyrazole Moiety in The Field of Cancer, Int J Pharm Pharm Sci, 4 (2012) 98�104; Qian, Y., Ma, G.-Y., Yang, Y., Cheng, K., Zheng, Q.-Z., Mao, W.-J., Shi, L., Zhu, H.-L., Synthesis, molecular modeling and biological evaluation of dithiocarbamates as novel antitubulin agents (2010) Bioorg. Med. Chem., 18, pp. 4310-4316; Ducki, S., Antimitotic chalcones and related compounds as inhibitors of tubulin assembly (2009) Anti-Cancer Agents Med. Chem., 9, pp. 336-347; Ducki, S., The development of chalcones as promising anticancer agents (2007) IDrugs, 10, pp. 42-46; Rappl, C., Barbier, P., Bourgarel-Rey, V., Gre�goire, C., Gilli, R., Carre, M., Combes, S., Peyrot, V., Interaction of 4-arylcoumarin analogues of combretastatins with microtubule network of HBL100 cells and binding to tubulin (2006) Biochemistry, 45, pp. 9210-9218; Kim, D.Y., Kim, K.-H., Kim, N.D., Lee, K.Y., Han, C.K., Yoon, J.H., Moon, S.K., Seong, B.L., Design and biological evaluation of novel tubulin inhibitors as antimitotic agents using a pharmacophore binding model with tubulin (2006) J. Med. Chem., 49, pp. 5664-5670; Edwards, M.L., Stemerick, D.M., Sunkara, P.S., Chalcones: a new class of antimitotic agents (1990) J. Med. Chem., 33, pp. 1948-1954; Herman, G., Busson, S., Gorbunoff, M.J., Mauduit, P., TimasheffIMA, S.N., Rossignol, B., Colchicine analogues that bind reversibly to tubulin define microtubular requirements for newly synthesized protein secretion in rat lacrimal gland (1989) Cell Biol., 86, pp. 4515-4519; Ducki, S., Mackenzie, G., Greedy, B., Armitage, S., Dit Chabert, J.F., Bennett, E., Nettles, J., Lawrence, N.J., Combretastin-like chalcones as inhibitors of microtubule polymerization. Part 2: structure-based discovery of alpha-aryl chalcones (2009) Bioorg. Med. Chem., 17, pp. 7711-7722; Dongre, R.S., Bhat, A.R., Meshram, J.S., Anticancer activity of assorted annulated pyrimidine: a comprehensive review (2014) Am. J. Pharm. Tech. Res., 4, pp. 138-155; Joshi, V.D., Kshirsagar, M.D., Singhal, S., Synthesis and pharmacological study of some novel pyrimidines (2012) Der Pharmacia Sinica, 3, pp. 343-348; Havrylyuk, D., Roman, O., Lesyk, R., Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline�thiazolidine-based hybrids (2016) Eur. Med. Chem., 113, pp. 145-166; Kant, R., Kumar, D., Agarwal, D., Gupta, R.D., Tilak, R., Awasthi, S.K., Agarwal, A., Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities (2016) Eur. Med. Chem., 113, pp. 34-49; Bhattacharyya, B., Panda, D., Gupta, S., Banerjee, M., Anti-mitotic activity of colchicine and the structural basis for its interaction with tubulin (2008) Med. Res. Rev., 28, pp. 155-183; Guo, L., Yang, C., Zheng, L., Xia, W., Visible light-mediated oxidative quenching reaction to electron-rich epoxides: highly regioselective synthesis of ?-bromo(di)ketones and mechanism study (2013) Org. Biomol. Chem., 11, pp. 5787-5792; Skehan, P., Monk, A., Scudiero, D.A., Shoemaker, R.H., Paull, K.D., DTP, DCTD Tumor repository a catalog of in vitro cell lines, transplantable animal and human tumors and micro assays (1991) J. Natl. Cancer Inst., 83, pp. 757-766; Liliom, K., Lehotzky, A., Molnar, A., Ovadi, J., Characterization of tubulin-alkaloid interactions by enzyme-linked immunosorbent assay (1995) Anal. Biochem., 228, pp. 18-26
dcterms.sourceScopus

Files

Original bundle

Now showing 1 - 1 of 1
Thumbnail Image
Name:
avatar_scholar_128.png
Size:
2.73 KB
Format:
Portable Network Graphics
Description:
Download

Collections

Faculty Of Pharmacy Research Paper