Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of ?-bromo-6H-1,3,4- oxadiazine derivatives

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dc.contributor.author Mohareb R.M.
dc.contributor.author Schatz J.
dc.contributor.other Faculty of Pharmacy
dc.contributor.other Organic Chemistry Department
dc.contributor.other October University for Modern Science and Arts University
dc.contributor.other El-Wahaat Road
dc.contributor.other October City
dc.contributor.other Egypt; Department of Chemistry
dc.contributor.other Faculty of Science
dc.contributor.other Cairo University
dc.contributor.other Giza
dc.contributor.other A.R.
dc.contributor.other Egypt; Department Chemie und Pharmazie - Organische Chemie i
dc.contributor.other Friedrich-Alexander-Universit�t Erlangen-N�rnberg
dc.contributor.other Henkestra�e 42
dc.contributor.other D-91054 Erlangen
dc.contributor.other Germany
dc.date.accessioned 2020-01-25T19:58:31Z
dc.date.available 2020-01-25T19:58:31Z
dc.date.issued 2011
dc.identifier.issn 9680896
dc.identifier.other https://doi.org/10.1016/j.bmc.2011.02.051
dc.identifier.other PubMed ID 21435889
dc.identifier.uri https://t.ly/ZEKZB
dc.description Scopus
dc.description.abstract Cyanoacetylhydrazine reacted with the ?-bromoacetophenones 2a,b to give hydrazide-hydrazone derivatives 3a,b. The latter products were cyclized to the 1,3,4-oxadiazine derivatives 4a,b. Bromination of the latter products gave the 6-bromo-6H-1,3,4-oxadiazine derivatives 5a,b which underwent a series of cross-coupling reactions. The antitumor evaluation of the newly synthesized products against the three cancer cells namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of them have high inhibitory effect towards three cell lines which is higher than the standard. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity. � 2011 Published by Elsevier Ltd. All rights reserved. en_US
dc.description.uri https://www.scimagojr.com/journalsearch.php?q=25786&tip=sid&clean=0
dc.language.iso English en_US
dc.relation.ispartofseries Bioorganic and Medicinal Chemistry
dc.relation.ispartofseries 19
dc.subject 1,3,4-Oxadiazine en_US
dc.subject Anti-leishmanial en_US
dc.subject Anti-tumor en_US
dc.subject Cross-coupling en_US
dc.subject Hydrazide-hydrazone en_US
dc.subject Pyran en_US
dc.subject 1,3,4 oxadiazine derivative en_US
dc.subject 2 (4 bromoacetophenon omega yl) 3 (4 bromophenyl) 5 cyano 6 cyanomethylpyran en_US
dc.subject 2 (4 bromoacetophenon omega yl) 3 (4 nitrophenyl) 5 cyano 6 cyanomethylpyran en_US
dc.subject 2 (4 nitroacetophenon omega yl) 3 (4 bromophenyl) 5 cyano 6 cyanomethylpyran en_US
dc.subject 2 (4 nitroacetophenon omega yl) 3 (4 nitrophenyl) 5 cyano 6 cyanomethylpyran en_US
dc.subject 2 [5 (4 bromophenyl) 6 (4 bromophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 bromophenyl) 6 bromo 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 bromophenyl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 nitrophenyl) 6 (4 bromophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 nitrophenyl) 6 (4 nitrophenylacet omega yl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 nitrophenyl) 6 bromo 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject 2 [5 (4 nitrophenyl) 6h 1,3,4 oxadiazin 2 yl]acetonitrile en_US
dc.subject amphotericin B en_US
dc.subject cyanoacetylhydrazido n (4 bromophenyl alpha bromoaceto)hydrazone en_US
dc.subject cyanoacetylhydrazido n (4 nitrophenyl alpha bromoaceto)hydrazone en_US
dc.subject doxorubicin en_US
dc.subject hydrazide derivative en_US
dc.subject hydrazone derivative en_US
dc.subject unclassified drug en_US
dc.subject amastigote en_US
dc.subject antineoplastic activity en_US
dc.subject article en_US
dc.subject bromination en_US
dc.subject cancer cell en_US
dc.subject cell strain MCF 7 en_US
dc.subject controlled study en_US
dc.subject cross coupling reaction en_US
dc.subject cyclization en_US
dc.subject cycloaddition en_US
dc.subject drug structure en_US
dc.subject growth inhibition en_US
dc.subject human en_US
dc.subject human cell en_US
dc.subject Leishmania donovani en_US
dc.subject nonhuman en_US
dc.subject Suzuki reaction en_US
dc.subject Antineoplastic Agents en_US
dc.subject Cell Line, Tumor en_US
dc.subject Cyclization en_US
dc.subject Drug Screening Assays, Antitumor en_US
dc.subject Halogenation en_US
dc.subject Heterocyclic Compounds en_US
dc.subject Humans en_US
dc.subject Hydrazones en_US
dc.subject Leishmania en_US
dc.subject Parasitic Sensitivity Tests en_US
dc.subject Pyrans en_US
dc.subject Leishmania donovani en_US
dc.title Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of ?-bromo-6H-1,3,4- oxadiazine derivatives en_US
dc.type Article en_US
dcterms.isReferencedBy Shindy, H.A., El-Maghraby, M.A., Eissa, F.M., (2006) Dyes Pigm., 70, p. 110; Mazouz, F., Lebreton, L., Milcent, R., Burstein, C., (1988) Eur. J. Med. Chem., 23, p. 441; Forchiassin, M., Risaliti, A., Russo, C., (1981) Tetrahedron, 37, p. 2921; Yamazaki, N., Kibayashi, C., (1997) Tetrahedron Lett., 26, p. 4623; Singh, S., K, L.H., Athar, F., Azam, A., (2005) Eur. J. Pharm. Sci., 25, p. 255; Kaleta, K., Fleischhauer, J., G�rls, H., Beckert, R., Imhof, W.J., (2009) Organomet. Chem., 23, p. 3800; Muehlebach, M., Boeger, M., Cederbaum, F., Cornes, D., Friedmann, A.A., Glock, J., Niderman, T., Wagner, T., (2009) Bioorg. Med. Chem., 17, p. 4241; Ke, S.Y., Liu, Q.X., Wang, N., Yang, Q., Li, Z., (2009) Eur. J. Med. Chem., 44, p. 2113; Bor�n, L., Martin-Matute, B., Xu, Y., Cordova, A., B�ckvall, J.E., (2006) Chem. Eur. J., 12, p. 225; Srivastava, R.M., De Morais, L.P., De Melo, S.C., Souto, G.B., Carpenter De Carvalho, L.T., (2006) Tetrahedron Lett., 47, p. 3173; Saracoglu, N., (2007) Tetrahedron, 63, p. 4199; Tahdi, A.S., Titouani, L., Soufiaoui, M., Komiha, N., Kabbaj, O.K., Hegazi, S., Mazzah, A., Eddaif, A., (2002) Tetrahedron, 58, p. 1507; Todd, L., Graybill, R.E., Carla, T., Helaszek, M.A., Ator, J.S., (1995) Bioorg. Med. Chem. Lett., 5, p. 1197; Frank, G., Riddell, E., Turner, S., (1979) Tetrahedron, 35, p. 1311; Wiessler, M., (1975) Tetrahedron Lett., 16, p. 2575; Muehlebach, M., Boeger, M., Cederbaum, F., Cornes, D., Friedmann, A.A., Glock, J., Niderman, T., Wagner, T., (2009) Bioorg. Med. Chem., 17, p. 4241; Vasiliev, N.V., Lyashenko, Y.E., Patalakha, A.E., Sokolski, G.A., (1993) J. Fluorine Chem., p. 227; Moody, C.J., (1982) Adv. Heterocycl. Chem., 30, p. 1; Padwa, A., Eisenbarth, P., (1985) Tetrahedron, 41, p. 283; Riddell, F.G., Turner, E.S., (1979) Tetrahedron, 35, p. 1311; Tiecco, M., Testaferri, L., Marini, F., (1996) Tetrahedron, 52, p. 11841; Job, A., Janeck, C.F., Bettray, W., Peters, R., Enders, D., (2002) Tetrahedron, 58, p. 2253; Mohamed, A.A., Radwan, M.E., (2007) Bioorg. Med. Chem., 15, p. 1206; Muehlebach, M., Boeger, M., Cederbaum, F., Cornes, D., Friedmann, A.A., Glock, J., Niderman, T., Wanger, T., (2009) Bioorg. Med. Chem., 17, p. 4241; Von Angerer, E., Strohmeier, J., (1987) J. Med. Chem., 30, p. 131; Glamkowski, E.J., Fortunato, J.M., Spaulding, T.C., Wilker, J.C., Ellis, D.B., (1985) J. Med. Chem., 28, p. 66; Unangst, P.C., Carethers, M.E., Webster, K., Janik, G.M., Robichaud, L.J., (1984) J. Med. Chem., 27, p. 1629; Sano, H., Noguchi, T., Miyajima, A., Hashimoto, Y., Miyachi, H., (2006) Bioorg. Med. Chem. Lett., 16, p. 3068; Perregaard, J., Arnt, J., Boegesoe, K.P., Hyttel, J., Sanchez, C., (1992) J. Med. Chem., 35, p. 1092; Cole, D.C., Ellingboe, J.W., Lennox, W.J., Mazandarani, H., Smith, D.L., Stock, J.R., Zhang, G.M., Schechter, L.E., (2005) Bioorg. Med. Chem. Lett., 15, p. 379; Li, Q., Li, T.M., Woods, K.W., Gu, W.Z., Cohen, J., Stoll, V.S., Galicia, T., Sham, H.L., (2005) Bioorg. Med. Chem. Lett., 15, p. 2918; Xu, H., Liu, W.Q., Fan, L.L., Chen, Y., Yang, L.M., Lv, L., Zheng, Y.T., (2008) Chem. Pharm. Bull., 56, p. 720; Hermecz, I., (2003) Adv. Heterocycl. Chem., 65, p. 173; Ternon, M., Outurquin, F., Paulmier, C., (2001) Tetrahedron, 57, p. 10259; Mohareb, R.M., Mohamed, A.A., (2010) Molecules, 15, p. 3602; Mohareb, R.M., El-Arab, E.E., El-Sharkawy, K.A., (2009) Sci. Pharm., 77, p. 355; Batty, D., Langlois, Y., (1993) Tetrahedron Lett., 34, p. 457; Kennedy, J.W., Hall, D.G.J., (2003) Organomet. Chem., 680, pp. 263-270
dcterms.source Scopus
dc.identifier.doi https://doi.org/10.1016/j.bmc.2011.02.051
dc.identifier.doi PubMed ID 21435889
dc.Affiliation October University for modern sciences and Arts (MSA)


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