{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,30]],"date-time":"2025-10-30T11:30:38Z","timestamp":1761823838174,"version":"3.40.5"},"reference-count":45,"publisher":"Walter de Gruyter GmbH","issue":"4","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2016,4,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>Dihydrochalcones are polyphenols that exhibit a diversity of bioactivities, namely anti-inflammatory, antimicrobial and antiviral. We have explored the synthetic access to such molecular entities, and describe now an easy and scalable approach based on reduction of the olefinic double bond of chalcone precursors via <jats:italic>in situ<\/jats:italic> hydrogenation with the system Et<jats:sub>3<\/jats:sub>SiH-Pd\/C in very high yield. The intermediate chalcones were synthesized also by a simple and efficient microwave-assisted Claisen\u2013Schmidt condensation of aromatic aldehydes with acetophenones, conveniently protected with ethoxymethyl ether, if required. Chalcones were obtained as single reaction product in high yield in 2\u20133 h, while under conventional conditions at room temperature the reaction was carried out with completion only after 24 h. In addition, microwave irradiation has proven very efficient for deprotection of ethoxymethyl ether with iron chloride in only 10 min and very high yield.<\/jats:p>","DOI":"10.1515\/pac-2016-0303","type":"journal-article","created":{"date-parts":[[2016,6,6]],"date-time":"2016-06-06T10:01:54Z","timestamp":1465207314000},"page":"349-361","source":"Crossref","is-referenced-by-count":8,"title":["An easy approach to dihydrochalcones <i>via<\/i> chalcone <i>in situ<\/i> hydrogenation"],"prefix":"10.1515","volume":"88","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0840-6289","authenticated-orcid":false,"given":"Ana R.","family":"Jesus","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Carbohydrate Chemistry Group, Edif\u00edcio C8, 5\u00b0 piso, 1749-016, Lisboa, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7393-8556","authenticated-orcid":false,"given":"Ana P.","family":"Marques","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de FTICR e Espectrometria de Massa Estrutural, Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, 1749-016 Lisboa, Portugal"}]},{"given":"Am\u00e9lia P.","family":"Rauter","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica e Bioqu\u00edmica, Faculdade de Ci\u00eancias, Universidade de Lisboa, Carbohydrate Chemistry Group, Edif\u00edcio C8, 5\u00b0 piso, 1749-016, Lisboa, Portugal"}]}],"member":"374","published-online":{"date-parts":[[2016,5,19]]},"reference":[{"key":"2024030511044860174_j_pac-2016-0303_ref_001","doi-asserted-by":"crossref","unstructured":"D. Batovska, I. Todorova. Cur. Clin. Pharm. 5, 1 (2010).","DOI":"10.2174\/157488410790410579"},{"key":"2024030511044860174_j_pac-2016-0303_ref_002","doi-asserted-by":"crossref","unstructured":"P. Singh, A. Anand, V. Kumar. Eur. J. Med. Chem. 85, 758 (2014).","DOI":"10.1016\/j.ejmech.2014.08.033"},{"key":"2024030511044860174_j_pac-2016-0303_ref_003","doi-asserted-by":"crossref","unstructured":"A. G\u00f3mez-Rivera, H. Aguilar-Mariscal, N. Romero-Ceronio, L. F. Roa-de la Fuente, C. E. Lobato-Garc\u00eda. Bioorg. Med. Chem. Lett.23, 5519 (2013).","DOI":"10.1016\/j.bmcl.2013.08.061"},{"key":"2024030511044860174_j_pac-2016-0303_ref_004","doi-asserted-by":"crossref","unstructured":"Y. H. Kim, J. Kim, H. Park, H. H. P. Kim. Biol. Pharm. Bull.30, 1450 (2007).","DOI":"10.1248\/bpb.30.1450"},{"key":"2024030511044860174_j_pac-2016-0303_ref_005","doi-asserted-by":"crossref","unstructured":"D. K. Mahapatra, S. K. Bharti, S. Asati. Eur. J. Med. Chem.101, 496 (2015).","DOI":"10.1016\/j.ejmech.2015.06.052"},{"key":"2024030511044860174_j_pac-2016-0303_ref_006","doi-asserted-by":"crossref","unstructured":"T. Doan, D. Tran. Pharmac. Pharm.2, 282 (2011).","DOI":"10.4236\/pp.2011.24036"},{"key":"2024030511044860174_j_pac-2016-0303_ref_007","doi-asserted-by":"crossref","unstructured":"S. Nielsen, M. Larsen, T. Boesen, K. Sch\u00f8nning, H. Kromann. J. Med. Chem. 48, 2667 (2005).","DOI":"10.1021\/jm049424k"},{"key":"2024030511044860174_j_pac-2016-0303_ref_008","doi-asserted-by":"crossref","unstructured":"Y. Nakamura, S. Watanabe, N. Miyake, H. Kohno, T. Osawa. J. Agric. Food Chem.51, 3309 (2003).","DOI":"10.1021\/jf0341060"},{"key":"2024030511044860174_j_pac-2016-0303_ref_009","unstructured":"M. L. Go, X. Wu, X. L. Liu. Curr. Med. Chem.12, 481 (2005)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_010","doi-asserted-by":"crossref","unstructured":"S. Syam, S. I. Abdelwahab, M. A. Al-Mamary, A. Mohan. Molecules17, 6179 (2012).","DOI":"10.3390\/molecules17066179"},{"key":"2024030511044860174_j_pac-2016-0303_ref_011","unstructured":"B. S. Jayashree, S. Arora, K. N. Venugopala. Asian J. Chem.20, 1 (2008)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_012","unstructured":"K. V. Gaikwad, S. V. Gaikwad, S. B. Jadhav, S. D. Rathod. Indian J. Chem.49B, 131 (2010)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_013","doi-asserted-by":"crossref","unstructured":"X. He, S. E. Kassab, G. Heinzl, F. Xue. Tetrahedron Lett.56, 1034 (2015).","DOI":"10.1016\/j.tetlet.2014.12.135"},{"key":"2024030511044860174_j_pac-2016-0303_ref_014","doi-asserted-by":"crossref","unstructured":"J. Somsrisa, P. Meepowpan, S. Krachodnok, H. Thaisuchat, S. Punyanitya, N. Nantasaen, W. Pompimon. Molecules18, 6898 (2013).","DOI":"10.3390\/molecules18066898"},{"key":"2024030511044860174_j_pac-2016-0303_ref_015","doi-asserted-by":"crossref","unstructured":"M. Awouafack, S. Kouam, H. Hussain, D. Ngamga, P. Tane, B. Schulz, I. R. Green, K. Krohn. Planta Med.74, 50 (2008).","DOI":"10.1055\/s-2007-993782"},{"key":"2024030511044860174_j_pac-2016-0303_ref_016","doi-asserted-by":"crossref","unstructured":"A. Bentes, R. Borges, W. Monteiro, L. Macedo, C. Alves. Molecules16, 1749 (2011).","DOI":"10.3390\/molecules16021749"},{"key":"2024030511044860174_j_pac-2016-0303_ref_017","doi-asserted-by":"crossref","unstructured":"M. M. D. Mohammed, A.-H.A. Hamdy, N. M. El-Fiky, W. S. A. Mettwally, A. A. El-Beih, N. Kobayashi. Nat. Prod. Res.28, 377 (2014).","DOI":"10.1080\/14786419.2013.869694"},{"key":"2024030511044860174_j_pac-2016-0303_ref_018","doi-asserted-by":"crossref","unstructured":"M. L. Climent, H. Garcia, J. Primo.Catal. Lett.4, 85 (1990).","DOI":"10.1007\/BF00764874"},{"key":"2024030511044860174_j_pac-2016-0303_ref_019","doi-asserted-by":"crossref","unstructured":"K. Yoshizawa, T. Shioiri. Tetrahedron Lett.47, 4943 (2006).","DOI":"10.1016\/j.tetlet.2006.05.021"},{"key":"2024030511044860174_j_pac-2016-0303_ref_020","unstructured":"M. R. Ahmad, V. G. Sastry, N. Bano. J. Pharm. Res.4, 2354 (2011)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_021","doi-asserted-by":"crossref","unstructured":"X. Fang, B. Yang, Z. Cheng, P. Zhang, M. Yang. Res. Chem. Intermed.40, 1715 (2014).","DOI":"10.1007\/s11164-013-1076-5"},{"key":"2024030511044860174_j_pac-2016-0303_ref_022","doi-asserted-by":"crossref","unstructured":"T. Narender, K. P. Reddy. Tetrahedron Lett.48, 3177 (2007).","DOI":"10.1016\/j.tetlet.2007.03.054"},{"key":"2024030511044860174_j_pac-2016-0303_ref_023","doi-asserted-by":"crossref","unstructured":"T. Narender, K. Venkateswarlu, B. V. Nayak, S. Sarkar. Tetrahedron Lett.52, 5794 (2011).","DOI":"10.1016\/j.tetlet.2011.08.120"},{"key":"2024030511044860174_j_pac-2016-0303_ref_024","doi-asserted-by":"crossref","unstructured":"S. Eddarir, N. Cotelle, Y. Bakkoura, C. Roland. Tetrahedron Lett.44, 5359 (2003).","DOI":"10.1016\/S0040-4039(03)01140-7"},{"key":"2024030511044860174_j_pac-2016-0303_ref_025","doi-asserted-by":"crossref","unstructured":"L. C. C. Vieira, M. W. Paix\u00e3o, A. G. Corr\u00eaa. Tetrahedron Lett. 53, 2715 (2012).","DOI":"10.1016\/j.tetlet.2012.03.079"},{"key":"2024030511044860174_j_pac-2016-0303_ref_026","doi-asserted-by":"crossref","unstructured":"X. Wu, H. Neumann, A. Spannenberg, T. Schulz, H. Jiao, M. Beller. J. Am. Chem. Soc.132, 14596 (2010).","DOI":"10.1021\/ja1059922"},{"key":"2024030511044860174_j_pac-2016-0303_ref_027","doi-asserted-by":"crossref","unstructured":"T. Guo, Q. Jiang, L. Yu, Z. Yu. Chinese J. Catal.36, 78 (2015).","DOI":"10.1016\/S1872-2067(14)60247-3"},{"key":"2024030511044860174_j_pac-2016-0303_ref_028","doi-asserted-by":"crossref","unstructured":"K. Tabatabaeian, M. Mamaghani, N. O. Mahmoodi, E. Keshavarz. Arkivoc2, 68 (2009).","DOI":"10.3998\/ark.5550190.0010.208"},{"key":"2024030511044860174_j_pac-2016-0303_ref_029","unstructured":"A. Hasaninejad, A. Zare, L. Balooty, H. Mehregan, M. Shekouhy. Syn. Comm. 1, 488 (2010)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_030","doi-asserted-by":"crossref","unstructured":"Y. Zhou, X. Li, S. Hou, J. Xu. J. Mol.Cat. A Chem.365, 203 (2012).","DOI":"10.1016\/j.molcata.2012.09.005"},{"key":"2024030511044860174_j_pac-2016-0303_ref_031","doi-asserted-by":"crossref","unstructured":"L. Zhang, W. Zhang, X. Wang, K. Bao, G. Lu, J. Lin. Lett. Org. Chem. 5, 370 (2008).","DOI":"10.2174\/157017808784872025"},{"key":"2024030511044860174_j_pac-2016-0303_ref_032","unstructured":"J.-P. Li, Y. X. Zhang, Y. Ji. J. Chinese Chem. Soc. 55, 390 (2008)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_033","doi-asserted-by":"crossref","unstructured":"J. Jr. Dudash, X. Zhang, R. E. Zeck, S. G. Johnson, G. G. Cox, B. R. Conway, P. J. Rybczynski, K. T. Demarest. Bioorg. Med. Chem. Lett.14, 5121 (2004).","DOI":"10.1016\/j.bmcl.2004.07.082"},{"key":"2024030511044860174_j_pac-2016-0303_ref_034","doi-asserted-by":"crossref","unstructured":"Y. Suzuki, K. Uchida. in Methods in Biotechnology: Carbohydrate Biotechnology Protocols, C. Bucke (Ed.), vol. 10, pp. 297\u2013312, Humana Press, Totowa, New Jersey (1999).","DOI":"10.1007\/978-1-59259-261-6_24"},{"key":"2024030511044860174_j_pac-2016-0303_ref_035","doi-asserted-by":"crossref","unstructured":"Z. Han, M. C. Achilonu, P. S. Kendrekar, E. Joubert, D. Ferreira, S. L. Bonnet, J. H. van der Westhuizen. J. Nat. Prod.77, 583 (2014).","DOI":"10.1021\/np4008443"},{"key":"2024030511044860174_j_pac-2016-0303_ref_036","doi-asserted-by":"crossref","unstructured":"E. Katengua-Thamahane, J. L. Marnewick, O. R. Ajuwon, N. N. Chegou, G. Sz\u00fccs, P. Ferdinandy, T. Csont, C. Csonka, J. van Rooyen. J. Inflamm. 11, 41 (2014).","DOI":"10.1186\/s12950-014-0041-4"},{"key":"2024030511044860174_j_pac-2016-0303_ref_037","doi-asserted-by":"crossref","unstructured":"K. Henmi, Y. Hiwatashi, E. Hikita, N. Toyama, T. Hirano. Biol. Pharm. Bull. 32, 1109 (2009).","DOI":"10.1248\/bpb.32.1109"},{"key":"2024030511044860174_j_pac-2016-0303_ref_038","doi-asserted-by":"crossref","unstructured":"J. Rojas, M. Paya, L. Devesa, J. N. Dominguez, M. Ferr\u00e1ndiz. Naunyn-Schmiedeberg\u2019sArch. Pharmacol.368, 225 (2003).","DOI":"10.1007\/s00210-003-0780-x"},{"key":"2024030511044860174_j_pac-2016-0303_ref_039","unstructured":"A. H. More, C. S. Ramaa. Indian J. Chem.49B, 364 (2010)."},{"key":"2024030511044860174_j_pac-2016-0303_ref_040","doi-asserted-by":"crossref","unstructured":"D. Kakati, J. C. Sarma. Chem. Central J.5, 8 (2011).","DOI":"10.1186\/1752-153X-5-8"},{"key":"2024030511044860174_j_pac-2016-0303_ref_041","doi-asserted-by":"crossref","unstructured":"D. R. Palleros. J. Chem. Edu. 81, 1345 (2004).","DOI":"10.1021\/ed081p1345"},{"key":"2024030511044860174_j_pac-2016-0303_ref_042","doi-asserted-by":"crossref","unstructured":"L. Xia, M. Narasimhulu, X. Li, J.-J. Shim, Y. R. Lee. Bull. Korean Chem. Soc.31, 664 (2010).","DOI":"10.5012\/bkcs.2010.31.03.664"},{"key":"2024030511044860174_j_pac-2016-0303_ref_043","doi-asserted-by":"crossref","unstructured":"P. K. Mandal, J. S. McMurray. J. Org. Chem.72, 6599 (2007).","DOI":"10.1021\/jo0706123"},{"key":"2024030511044860174_j_pac-2016-0303_ref_044","doi-asserted-by":"crossref","unstructured":"D. Villemin, B. Nechab. J. Chem. Res. (S). 9, 432 (2000).","DOI":"10.3184\/030823400103167976"},{"key":"2024030511044860174_j_pac-2016-0303_ref_045","unstructured":"G. I. Bolestova, Z. N. Parnes, D. N. Kursanov. J. Org. Chem. USSR (Engl. Transl.) 15, 1129 (1979)."}],"container-title":["Pure and Applied Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.degruyter.com\/view\/journals\/pac\/88\/4\/article-p349.xml","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/pac-2016-0303\/xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/pac-2016-0303\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,3,5]],"date-time":"2024-03-05T11:05:44Z","timestamp":1709636744000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/pac-2016-0303\/html"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,4,1]]},"references-count":45,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2016,4,6]]},"published-print":{"date-parts":[[2016,4,1]]}},"alternative-id":["10.1515\/pac-2016-0303"],"URL":"https:\/\/doi.org\/10.1515\/pac-2016-0303","relation":{},"ISSN":["1365-3075","0033-4545"],"issn-type":[{"type":"electronic","value":"1365-3075"},{"type":"print","value":"0033-4545"}],"subject":[],"published":{"date-parts":[[2016,4,1]]}}}