{"id":{"repo_id":"brazil-ufpb","oai_identifier":"oai:repositorio.ufpb.br:123456789/448"},"canonical_url":"https://search.dev.ndltd.org/etd/brazil-ufpb/oai:repositorio.ufpb.br:123456789/448","repository":{"repo_id":"brazil-ufpb","name":"Brazil UFPB","base_url":"https://repositorio.ufpb.br/oai/request"},"display":{"title":"Síntese de novos adutos de Morita-Baylis-Hillman com potencial atividade biológica.","abstract":"This work was designed using the concept of classical bioisosterism where isoelectronic OH groups were replaced by the CH3 group, aimed at finding a relationship between the lipossolubility of the adducts Morita-Baylis-Hillman (AMBH) and its biological activity. Was developed in this work, synthetic methodologies for the preparation of 16 AMBH unprecedented (47-62), getting good and high yields and moderate reaction times. Initially was synthesized AMBH 8 using the 2-hydroxyethyl Acrylate 45 as Michael acceptor, giving the adducts 47 (2-hydroxyethyl [2-(hy-droxy(2-nitrophenyl)methyl)] acrylate, 71%), 48 (2-hydroxyethyl [2-(hydro- xy(3-nitrophenyl)methyl)] acrylate, 50%), 49 (2-hydroxyethyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 62%), 50 (2-hydroxyethyl [2-(hydroxy(pyridin-2-yl)methyl)] acrylate, 94%), 51 (2-hydroxyethyl [2-(hydroxy(pyridin-3-yl) methyl)] acrylate, 83%), 52 (2-hydroxyethyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 80%), 53 (2-hydroxyethyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 67%), 54 (2-hydroxyethyl[2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 71%). The second step ofthe synthesis was the preparation of Propyl Acrylate (46), from acrylicacid and propanol (yield 98%), which was later used as Michael acceptorsin the synthesis of AMBH 55 (Propyl [2-(hydroxy(2-nitro-phenyl)methyl)]acrylate, 68%), 56 (Propyl [2-(hydroxy(3-nitrophenyl)methyl)] acrylate, 73%), 57 (Propyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 97%), 58 (Propyl [2-(hydroxy(pyridin-2-yl)methyl)]acrylate, 70%), 59 (Propyl [2-(hydroxy(pyridin-3-yl)methyl)acrylate], 80%), 60 (Propyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 66%), 61 (Propyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 64%), 62 (Propyl [2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 60%).","abstract_html":"This work was designed using the concept of classical bioisosterism where isoelectronic OH groups were replaced by the CH3 group, aimed at finding a relationship between the lipossolubility of the adducts Morita-Baylis-Hillman (AMBH) and its biological activity. Was developed in this work, synthetic methodologies for the preparation of 16 AMBH unprecedented (47-62), getting good and high yields and moderate reaction times. Initially was synthesized AMBH 8 using the 2-hydroxyethyl Acrylate 45 as Michael acceptor, giving the adducts 47 (2-hydroxyethyl [2-(hy-droxy(2-nitrophenyl)methyl)] acrylate, 71%), 48 (2-hydroxyethyl [2-(hydro- xy(3-nitrophenyl)methyl)] acrylate, 50%), 49 (2-hydroxyethyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 62%), 50 (2-hydroxyethyl [2-(hydroxy(pyridin-2-yl)methyl)] acrylate, 94%), 51 (2-hydroxyethyl [2-(hydroxy(pyridin-3-yl) methyl)] acrylate, 83%), 52 (2-hydroxyethyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 80%), 53 (2-hydroxyethyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 67%), 54 (2-hydroxyethyl[2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 71%). The second step ofthe synthesis was the preparation of Propyl Acrylate (46), from acrylicacid and propanol (yield 98%), which was later used as Michael acceptorsin the synthesis of AMBH 55 (Propyl [2-(hydroxy(2-nitro-phenyl)methyl)]acrylate, 68%), 56 (Propyl [2-(hydroxy(3-nitrophenyl)methyl)] acrylate, 73%), 57 (Propyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 97%), 58 (Propyl [2-(hydroxy(pyridin-2-yl)methyl)]acrylate, 70%), 59 (Propyl [2-(hydroxy(pyridin-3-yl)methyl)acrylate], 80%), 60 (Propyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 66%), 61 (Propyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 64%), 62 (Propyl [2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 60%).","abstract_has_math":false,"creators":["Silva, Fábio Pedrosa Lins."],"institution":"Química","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2013,"date_issued":"2013-09-09","date_published":"2013-09-09","updated_at":"2026-07-24T01:17:54Z","subjects":["Química orgânica","Adutos de Morita-Baylis-Hillman","Bioisosterismo clássico","Organic chemistry","Morita-Baylis-Hillman ads","Classic bioswatcher"],"languages":["pt"],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://repositorio.ufpb.br/jspui/handle/123456789/448","outbound_label":"Repository record","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Silva, Fábio Pedrosa Lins."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2013-09-09T20:44:43Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2013-09-09T20:44:43Z"]},{"key":"dc:date.issued","label":"Date","values":["2013-09-09"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Química"]},{"key":"dc:type","label":"Dc Type","values":["TCC"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Química orgânica","Adutos de Morita-Baylis-Hillman","Bioisosterismo clássico","Organic chemistry","Morita-Baylis-Hillman ads","Classic bioswatcher"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["pt"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://repositorio.ufpb.br/jspui/handle/123456789/448"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["This work was designed using the concept of classical bioisosterism where isoelectronic OH groups were replaced by the CH3 group, aimed at finding a relationship between the lipossolubility of the adducts Morita-Baylis-Hillman (AMBH) and its biological activity. Was developed in this work, synthetic methodologies for the preparation of 16 AMBH unprecedented (47-62), getting good and high yields and moderate reaction times. Initially was synthesized AMBH 8 using the 2-hydroxyethyl Acrylate 45 as Michael acceptor, giving the adducts 47 (2-hydroxyethyl [2-(hy-droxy(2-nitrophenyl)methyl)] acrylate, 71%), 48 (2-hydroxyethyl [2-(hydro- xy(3-nitrophenyl)methyl)] acrylate, 50%), 49 (2-hydroxyethyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 62%), 50 (2-hydroxyethyl [2-(hydroxy(pyridin-2-yl)methyl)] acrylate, 94%), 51 (2-hydroxyethyl [2-(hydroxy(pyridin-3-yl) methyl)] acrylate, 83%), 52 (2-hydroxyethyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 80%), 53 (2-hydroxyethyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 67%), 54 (2-hydroxyethyl[2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 71%). The second step ofthe synthesis was the preparation of Propyl Acrylate (46), from acrylicacid and propanol (yield 98%), which was later used as Michael acceptorsin the synthesis of AMBH 55 (Propyl [2-(hydroxy(2-nitro-phenyl)methyl)]acrylate, 68%), 56 (Propyl [2-(hydroxy(3-nitrophenyl)methyl)] acrylate, 73%), 57 (Propyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 97%), 58 (Propyl [2-(hydroxy(pyridin-2-yl)methyl)]acrylate, 70%), 59 (Propyl [2-(hydroxy(pyridin-3-yl)methyl)acrylate], 80%), 60 (Propyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 66%), 61 (Propyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 64%), 62 (Propyl [2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 60%)."]},{"key":"dc:title","label":"Title","values":["Síntese de novos adutos de Morita-Baylis-Hillman com potencial atividade biológica."]}]}],"canonical_facts":{"dc:creator":["Silva, Fábio Pedrosa Lins."],"dc:date.accessioned":["2013-09-09T20:44:43Z"],"dc:date.available":["2013-09-09T20:44:43Z"],"dc:date.issued":["2013-09-09"],"dc:description.abstract":["This work was designed using the concept of classical bioisosterism where isoelectronic OH groups were replaced by the CH3 group, aimed at finding a relationship between the lipossolubility of the adducts Morita-Baylis-Hillman (AMBH) and its biological activity. Was developed in this work, synthetic methodologies for the preparation of 16 AMBH unprecedented (47-62), getting good and high yields and moderate reaction times. Initially was synthesized AMBH 8 using the 2-hydroxyethyl Acrylate 45 as Michael acceptor, giving the adducts 47 (2-hydroxyethyl [2-(hy-droxy(2-nitrophenyl)methyl)] acrylate, 71%), 48 (2-hydroxyethyl [2-(hydro- xy(3-nitrophenyl)methyl)] acrylate, 50%), 49 (2-hydroxyethyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 62%), 50 (2-hydroxyethyl [2-(hydroxy(pyridin-2-yl)methyl)] acrylate, 94%), 51 (2-hydroxyethyl [2-(hydroxy(pyridin-3-yl) methyl)] acrylate, 83%), 52 (2-hydroxyethyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 80%), 53 (2-hydroxyethyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 67%), 54 (2-hydroxyethyl[2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 71%). The second step ofthe synthesis was the preparation of Propyl Acrylate (46), from acrylicacid and propanol (yield 98%), which was later used as Michael acceptorsin the synthesis of AMBH 55 (Propyl [2-(hydroxy(2-nitro-phenyl)methyl)]acrylate, 68%), 56 (Propyl [2-(hydroxy(3-nitrophenyl)methyl)] acrylate, 73%), 57 (Propyl [2-(hydroxy(4-nitrophenyl)methyl)] acrylate, 97%), 58 (Propyl [2-(hydroxy(pyridin-2-yl)methyl)]acrylate, 70%), 59 (Propyl [2-(hydroxy(pyridin-3-yl)methyl)acrylate], 80%), 60 (Propyl [2-(hydroxy(pyridin-4-yl)methyl)] acrylate, 66%), 61 (Propyl [2-((4-bromophenyl)(hydroxy)methyl)] acrylate, 64%), 62 (Propyl [2-(hydroxy(naphthalen-2-yl)methyl)] acrylate, 60%)."],"dc:identifier.uri":["https://repositorio.ufpb.br/jspui/handle/123456789/448"],"dc:language.iso":["pt"],"dc:publisher.department":["Química"],"dc:subject":["Química orgânica","Adutos de Morita-Baylis-Hillman","Bioisosterismo clássico","Organic chemistry","Morita-Baylis-Hillman ads","Classic bioswatcher"],"dc:title":["Síntese de novos adutos de Morita-Baylis-Hillman com potencial atividade biológica."],"dc:type":["TCC"]},"updated_at":"2026-07-24T01:17:54Z"}