Synthesis of sugar-biguanide hybrids to study their potential biological effects

• Autor(a) principal: Barateiro, João Filipe Nunes da Costa e Silva
• Data de Publicação: 2022
• Tipo de documento: Dissertação
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10362/144825
• topic: Domínio/Área Científica::Engenharia e Tecnologia::Engenharia Química

Synthesis of sugar-biguanide hybrids was attempted by starting the approach from dicyanamide salts, by use of acidic medium to activate the dicyanamide for amine addition to create a biguanide compound to be connected to a sugar by a triazole ring. Green Chemistry principles were considered to try and maintain the reaction as “green” as possible and that was partially achieved in the biguanide synthesis pathway. NMR was the primary tool for monitoring the success of the reactions. The reactions with the sugars were already known in literature, Galactose and Mannose derivatives were obtained, dimethyl, β-naphtyl and imidazole cyanoguanidine were obtained as well, the yields obtained varied, between 20-60%. The carbon NMRs allowed for a fast way to know if the guanidine reactions happened, with the appearance of a signal around 160 ppm, this facilitates identification and doesn’t waste as much resources.