Submitted by Sandra Pereira (srpereira@ufrrj.br) on 2017-05-12T14:19:07Z No. of bitstreams: 1 2010 - Henriqueta Talita Guimar?es Barboza.pdf: 10302674 bytes, checksum: 6daf4f88308c3c733615f0772d6db594 (MD5) / Made available in DSpace on 2017-05-12T14:19:07Z (GMT). No. of bitstreams: 1 2010 - Henriqueta Talita Guimar?es Barboza.pdf: 10302674 bytes, checksum: 6daf4f88308c3c733615f0772d6db594 (MD5) Previous issue date: 2010-03-04 / Twelve heterocyclic dialkylphosphorylhydrazones compounds were synthesized in this work. Dialkylphosphorylhydrazones were obtained through 3 steps of reaction. The first step consists on the synthesis of different dialkylphosphonates obtained by reaction of triethyl phosphate (PCl3) with 3 mols of the corresponding alcohol. The second step occurs by the reaction with dialkylphosphonates synthesized and hydrazine, producing dialkylphosphorylhydrazines. The third and last step is the condensation reaction of these dialkylphosphorylhydrazines with different heterocycle substituted aromatic aldehydes. The analysis of the 1H NMR spectra allowed to observe the stereoisomers E and Z, with the formation of E diastereisomer preferencially. All the compounds were characterized by 1H, 13C and 31P NMR, IR and mass spectroscopy. Tests in vitro with, Alternaria sp., Colletotrichum sp., Fusarium sp. e Fusarium solani, known as patogenic in papaya (Carica papaya L.) were performed in order to confirm if the compounds showed fungicide activity. The substance 6 B was the one with the best performance in the inhibition of all fungal growths. Finally, tests with acetylcholinesterase enzyme indicated that all substances did not inhibit this enzyme. Figure 2 - General structures of dialkylphosphoryhidrazones synthesized. R ? Ethyl; propyl; isopropyl e isobuthyl. X = O, Y, Z e W = CH; X = S, Y, Z e W = CH; X = NH, Y, Z e W = CH; X = NH, Y= CH, Z=CH e W = N; X = CH, Y= N, Z=CH e W = N; / Neste trabalho foram sintetizadas doze (12) novas dialquilfosforilidrazonas heteroc?clicas. Esses compostos foram obtidos utilizando-se tr?s etapas de rea??o. A primeira etapa consiste na s?ntese de diferentes fosfonatos de dialquila, obtidos por meio da rea??o do tricloreto de f?sforo (PCl3) com tr?s mols do ?lcool correspondente. A segunda etapa ocorre por meio da rea??o dos fosfonatos de dialquila sintetizados com a hidrazina, formando as dialquilfosforilidrazinas. A terceira e ?ltima etapa ? a condensa??o destas dialquilfosforilidrazinas com diferentes alde?dos heteroc?clicos. A an?lise dos espectros de RMN-1H indica a forma??o de diastereois?meros, E e Z, com predomin?ncia do diastereis?meros E. Todos os compostos obtidos foram caracterizados por RMN de H1 e C13 e P31, IV, an?lises de massas. Em seguida foram realizados testes in vitro para verificar se os mesmos possuem atividade fungicida sobre os fungos Alternaria sp., Colletotrichum sp., Fusarium sp. e Fusarium solani, conhecidos por serem pat?genos da cultura de mam?o (Carica papaya L.). O composto 6 B foi o que apresentou o melhor efeito fungicida sobre o crescimento de todos os fungos. Finalmente foram realizados testes com a enzima acetilcolinesterase a fim de observar a toxicidade dos compostos sintetizados frente a esta enzima. Figura 1- Estrututa gen?rica das dialquilfosforilidrazonas heteroc?clicas sintetizadas. R ? Etil; propil; isopropil e isobutil. X = O, Y, Z e W = CH; X = S, Y, Z e W = CH; X = NH, Y, Z e W = CH; X = NH, Y= CH, Z=CH e W = N; X = CH, Y= N, Z=CH e W = N.

Submitted by Maike Costa (maiksebas@gmail.com) on 2017-06-21T12:11:13Z No. of bitstreams: 1 arquivototal.pdf: 5280829 bytes, checksum: 081debefa3f10398a1c9461855ba5b9d (MD5) / Made available in DSpace on 2017-06-21T12:11:14Z (GMT). No. of bitstreams: 1 arquivototal.pdf: 5280829 bytes, checksum: 081debefa3f10398a1c9461855ba5b9d (MD5) Previous issue date: 2015-07-29 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / Two series based on the structure of 2,5-diaryl-1,3,4-oxadiazole were synthesized, 2-aryl-5-methyl-1,3,4-oxadiazole (1a,h) and 2-aryl-5- trifluoromethyl-1,3,4-oxadiazole (2a,e), and their biological activity were investigated. These compounds had their chemical structures characterized with spectrometric methods such as IR, 1H and 13C NMR. To characterize the compound 2-(2-acetoxyphenyl)-5-methyl-1,3,4- oxadiazole, it was necessary the use of two-dimensional NMR techniques (COSY, HMQC and HMBC) and his structural arrangement was analyzed by the crystallographic X-ray technique. Mass spectrometric investigation, unprecedented for this class of compound, was also performed. All compounds were tested against eight strains of Staphylococcus aureus, Escherichia coli and also against strains of Aspegilles fumigatus, Aspegilles flavus, Candida albicans, Candida albicans and Candida tropicalis. The results showed that compounds 1b, 1c, 1e, 1g, 2a and 2c, produced inhibition on the growth of species of bacteria and fungi, where the MIC was set between 512 to 1224 mg mL-1. While the compounds 1d, 1e, 1f, 1h, 2a and 2b were inactive, the compounds 1d, 1e, 1f, 1h, 2a and 2b reported a broad spectrum. / Duas séries do heterocíclico 1,3,4-oxadiazol foram sintetizadas, a 2-aril-5-metil-1,3,4-oxadiazol (1a, h) e a 2-aril-5-trifluormetil-1,3,4- oxadiazol (2a, e), obtendo cinco moléculas inéditas (1a, 1e, 2a, 2c e 2e). Todas as moléculas obtidas foram caracterizados pelas técnicas espectroscópicas de 1D de RMN 1H e 13C, IV e realizado o estudo inédito de espectroscopia de Massas. Para a caracterização do composto 2-(2- acetoxifenil)-5-metil-1,3,4-oxadiazol se fez necessário a utilização das técnicas bidimensionais de RMN COSY, HMQC e HMBC, bem como seu arranjo estrutural foi analisado pela técnica cristalográfica de Raios-X. Os oxadiazóis obtidos foram avaliadas frente a oito cepas de Staphylococcus aureus e Escherichia coli e oito cepas, incluindo, Aspegilles fumigatus ATCC 16913, Aspegilles flavus, Candida albicans, Candida albicans e Candida tropicalis. Os ensaios para avaliações da atividade biológica dos produtos foram realizados pela técnica de microdiluição em meio líquido, onde foi determinada a concentração Inibitória Mínima (CIM). Os resultados mostraram que os compostos (1b), (1c), (1e), (1g), (2a) e (2c), produziram inibição sobre o crescimento de espécies de bactérias e de fungos, onde a CIM ficou estabelecida entre 512 a 1224 mg/ml. Enquanto que os compostos 1d, 1e, 1f, 1h, 2a e 2b se apresentaram inativos. Já os compostos 1d, 1e, 1f, 1h, 2a e 2b relataram um amplo espectro.

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