{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T04:36:11Z","timestamp":1760243771331,"version":"build-2065373602"},"reference-count":14,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2012,9,27]],"date-time":"2012-09-27T00:00:00Z","timestamp":1348704000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molbank"],"abstract":"<jats:p>A tetraethylene pentamine-diamine (L4), the biggest compound in the family of dibenzylated diimine-polyamines (L1\u2013L4) has been synthesized by classical Schiff-base reaction between benzaldehyde and the diamine tetraethylenepentamine, and the structure was confirmed by elemental analysis, ESI-MS spectrometry and by IR and 1H-NMR spectroscopy.<\/jats:p>","DOI":"10.3390\/m779","type":"journal-article","created":{"date-parts":[[2012,9,28]],"date-time":"2012-09-28T07:00:25Z","timestamp":1348815625000},"page":"M779","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["N1-Benzylidene-N2-(2-((2-((2-(benzylideneamino)ethyl)amino) ethyl)amino)ethyl)ethane-1,2-diamine"],"prefix":"10.3390","volume":"2012","author":[{"given":"Javier","family":"Fern\u00e1ndez-Lodeiro","sequence":"first","affiliation":[{"name":"Grupo BIOSCOPE, Departamento de Qu\u00edmica F\u00edsica, Falcultad de Ciencias, Campus de Ourense, Universidad de Vigo, 32004, Ourense, Spain"}]},{"given":"Cristina","family":"N\u00fa\u00f1ez","sequence":"additional","affiliation":[{"name":"Grupo BIOSCOPE, Departamento de Qu\u00edmica F\u00edsica, Falcultad de Ciencias, Campus de Ourense, Universidad de Vigo, 32004, Ourense, Spain"},{"name":"Departamento de Qu\u00edmica, FCT-UNL, 2829-516 Monte de Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1633-8212","authenticated-orcid":false,"given":"Emilia","family":"B\u00e9rtolo","sequence":"additional","affiliation":[{"name":"Ecology Research Group, Department of Geographical and Life Sciences, Canterbury Christ Church University, Canterbury, Kent. CT1 1QU, UK"}]},{"given":"Jos\u00e9","family":"Capelo","sequence":"additional","affiliation":[{"name":"Grupo BIOSCOPE, Departamento de Qu\u00edmica F\u00edsica, Falcultad de Ciencias, Campus de Ourense, Universidad de Vigo, 32004, Ourense, Spain"},{"name":"Departamento de Qu\u00edmica, FCT-UNL, 2829-516 Monte de Caparica, Portugal"}]},{"given":"Carlos","family":"Lodeiro","sequence":"additional","affiliation":[{"name":"Grupo BIOSCOPE, Departamento de Qu\u00edmica F\u00edsica, Falcultad de Ciencias, Campus de Ourense, Universidad de Vigo, 32004, Ourense, Spain"},{"name":"Departamento de Qu\u00edmica, FCT-UNL, 2829-516 Monte de Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2012,9,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1042\/bj20031327","article-title":"A perspective of polyamine metabolism","volume":"376","author":"Wallace","year":"2003","journal-title":"Biochem J."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1042\/bj20020720","article-title":"Identification and characterization of a novel flavin-containing spermine oxidase of mammalian cell origin","volume":"367","author":"Vujcic","year":"2002","journal-title":"Biochem. J."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1038\/nrd2243","article-title":"Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases","volume":"6","author":"Casero","year":"2007","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1042\/bst0310393","article-title":"Polyamine analogues as anticancer drugs","volume":"31","author":"Wallace","year":"2003","journal-title":"Biochem. Soc. Trans."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1007\/s00726-007-0510-7","article-title":"Special issue: Polyamines and their Analogs in Cancer and other Diseases","volume":"33","author":"Agostinelli","year":"2007","journal-title":"Amino Acids"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"44826","DOI":"10.1074\/jbc.M308643200","article-title":"Chloride Accumulation and Swelling in Endosomes Enhances DNA Transfer by Polyamine-DNA Polyplexes","volume":"278","author":"Sonawane","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/S0009-2614(01)01414-2","article-title":"Switching from intramolecular energy transfer to intramolecular electron transfer by the action of pH and Zn(II) coordination","volume":"353","author":"Albelda","year":"2002","journal-title":"Chem. Phys. Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"11307","DOI":"10.1021\/jp036149p","article-title":"Energetics and dynamics of naphathalene polyaminic derivatives. Influence of structural design in the balance static vs dynamic excimer formation","volume":"107","author":"Pina","year":"2003","journal-title":"J. Phys. Chem. A"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1080\/10610270412331317512","article-title":"Fluorescent Type II Materials from Naphthylmethyl Polyamine Precursors","volume":"16","author":"Aucejo","year":"2004","journal-title":"Supramol. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"3410","DOI":"10.1016\/j.ica.2008.02.056","article-title":"Interaction of polyamine macrocycles with Zn(II) and ATP in aqueos solution. Binary and Ternary systems. A potentiometric, NMR and fluorescence emission studies","volume":"361","author":"Bazzicalupi","year":"2008","journal-title":"Inorg. Chim. Acta"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1016\/j.inoche.2009.07.011","article-title":"Exploiting anionic and cationic interactions with a new emissive imine-based \u03b2-naphtol molecular probe","volume":"12","author":"Fernandez","year":"2009","journal-title":"Inorg. Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"326","DOI":"10.1016\/j.tet.2010.11.040","article-title":"Novel versatile imine-enamine chemosensor based on 6-nitro-4-oxo-4H-chromene for ion detection in solution, solid and gas-phase: Synthesis, emission, computational and MALDI-TOF-Ms studies","volume":"67","author":"Carreira","year":"2011","journal-title":"Tetrahedron"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Bernardo, M.A., Gurrero, J.A., Garc\u00eda-Espa\u00f1a, E., Luis, S.V., Llinares, J.M., Pina, F., Ram\u00edrez, J.A., and Soriano, C. (1996). Thermodynamic, NMR and photochemical study on the acid-base behaviour or N,N'-dibenzylated polyamines and on their interactions with hexacyanocobaltate(III). J. Chem. Soc. Perkin Trans 2, 2335\u20132342.","DOI":"10.1039\/P29960002335"},{"key":"ref_14","unstructured":"The smaller parent compounds derived from 1,2-ethanediamine (L1), diethylenetriamine (L2), and triethylenetetramine (L3) were obtained by a similar methodology, using 0.038, 0.063 and 0.089 g of diamine, respectively. Compound L1: N1,N2-Dibenzylideneethane-1,2-diamine; Yield: 121 mg (84%); ESI-MS: m\/z (rel. int%): 237.13 (100) ([M+H]+); 1H NMR (CDCl3): \u03b4 = 8.1 (s, 2H, N=C\u2013H); 7.8 (m, 4H, C-Har); 7.2 (m, 6H, C-Har); 3.8 (s, 4H, CH2) ppm; IR (cm\u22121): 1647 (C=N, Imine), 1599, 1498 (C=C, Ar); Elemental analysis: Calcd for C16H16N2: C, 81.32; H, 6.82; N, 11.85. Found: C, 80.87; H, 7.02; N,12.05. Compound L2: N1-Benzylidene-N2-(2-(benzylideneamino)\u00acethyl)ethane-1,2-diamine; Yield: 103 mg (71%); ESI-MS: m\/z (rel. int%): 279.17 (100) ([M+H]+); 1H-NMR (CDCl3): \u03b4 = 8.2 (s, 2H, N=C\u2013H); 7.8\u20137.6 (m, 4H, C-Har); 7.4\u20137.2 (m, 6H, C-Har); 3.8 (m, 4H, CH2); 2.9 (m, 4H, CH2) ppm; IR (cm\u22121): 1649 (C=N, Imine), 1586, 1491 (C=C, Ar); Elemental analysis: Calcd for C18H21N3: C, 77.38; H, 7.58; N, 15.04. Found: C, 77.16; H, 8.03; N, 15.34. Compound L3: N1,N1\u2032-(Ethane-1,2-diyl)bis(N2-benzylideneethane-1,2-diamine); Yield: 132 mg (89%); ESI-MS: m\/z (rel. int%): 323.22 (100) ([M+H]+); 1H-NMR (CDCl3): \u03b4 = 8.1 (s, 2H, N=C\u2013H); 7.7\u20137.5 (m, 4H, C-Har); 7.4\u20137.1 (m, 6H, C-Har); 3.7\u20133.4 (m, 2H, CH2); 2.9\u20132.1 (m, 8H, CH2) ppm; IR (cm\u22121): 1656 (C=N, Imine), 1576, 1499 (C=C, Ar); Elemental analysis: Calcd for C20H26N4: C, 74.50; H, 8.13; N, 17.38. Found: C, 74.78; H, 8.16; N, 17.49."}],"container-title":["Molbank"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-8599\/2012\/4\/M779\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:52:36Z","timestamp":1760219556000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-8599\/2012\/4\/M779"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,9,27]]},"references-count":14,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2012,12]]}},"alternative-id":["M779"],"URL":"https:\/\/doi.org\/10.3390\/m779","relation":{},"ISSN":["1422-8599"],"issn-type":[{"type":"electronic","value":"1422-8599"}],"subject":[],"published":{"date-parts":[[2012,9,27]]}}}