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Insights into the anticancer activity of chiral alkylidene-β-lactams and alkyli...
Alves, Américo J. S.; Alves, Nuno G.; Laranjo, Mafalda; Gomes, Clara S. B.; Gonçalves, Ana Cristina; Ribeiro, Ana Bela Sarmento; Botelho, M. FilomenaChiral alkylidene-β-lactams and alkylidene-γ-lactams were synthesized and screened for their in vitro activity against four human cancer cell lines (melanoma, esophageal, lung and fibrosarcoma carcinoma). Alkylidene-β-lactams were synthesized via Wittig reaction of diverse phosphorus ylides with benzhydryl 6-oxopenicillanate, derived from 6-aminopenicillanic acid. Moreover, novel chiral alkylidene-γ-lactams wer...
Unveiling a family of spiro-β-lactams with anti-HIV and antiplasmodial activity...
Alves, Américo J. S.; Alves, Nuno G.; Bártolo, Inês; Fontinha, Diana; Caetano, Soraia; Prudêncio, Miguel; Taveira, Nuno; Melo, Teresa M. V. D. Pinho eThe molecular architecture of spirocyclic compounds has been widely explored within the medicinal chemistry field to obtain new compounds with singular three-dimensional pharmacophoric features and improved bioactivity. Herein, the synthesis of 68 new spirocyclopentene-β-lactams is described, resulting from a rational drug design and structural modulation of a highly promising lead compound BSS-730A, previously...
High instantaneous inhibitory potential of Bictegravir and the new Spiro-β-Lact...
Bártolo, Inês; Moranguinho, Inês; Gonçalves, Paloma; Diniz, Ana Rita; Borrego, Pedro; Martin, Francisco; Figueiredo, Inês; Gomes, PerpétuaIntegrase inhibitors (INIs) are an important class of drugs for treating HIV-2 infection, given the limited number of drugs active against this virus. While the clinical efficacy of raltegravir and dolutegravir is well established, the clinical efficacy of bictegravir for treating HIV-2 infected patients has not been determined. Little information is available regarding the activity of bictegravir against HIV-2...
Strategies and methodologies for the construction of spiro-γ-lactams: an update
Alves, Américo J. S.; Alves, Nuno G.; Soares, Maria I. L.; Pinho e Melo, Teresa M. V. D.Spiro-γ-lactams (spiropyrrolinin-2-ones) are a class of spirocyclic compounds that are present in a wide range of synthetic bioactive and naturally occurring molecules. The increasing attention to spirocyclic lactams in drug discovery has been accompanied by a growing interest in these compounds from a synthetic point of view, namely as synthetic building blocks in organic chemistry, due to their inherent rigid...
Synthesis and structure-activity relationships of new chiral spiro-β-lactams hi...
Alves, Nuno Guerreiro; Bártolo, Inês; Alves, Américo J. S.; Fontinha, Diana; Francisco, Denise; Lopes, Susana M. M.; Soares, Maria I. L.The synthesis and antimicrobial activity of new spiro-β-lactams is reported. The design of the new molecules was based on the structural modulation of two previously identified lead spiro-penicillanates with dual activity against HIV and Plasmodium. The spiro-β-lactams synthesized were assayed for their in vitro activity against HIV-1, providing relevant structure-activity relationship information. Among the te...
Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams
Alves, Nuno Guerreiro; Alves, Américo J. S.; Soares, Maria I. L.; Pinho e Melo, Teresa M. V. D.Spirocyclic molecules are widely recognized for their complex three-dimensional features and structural rigidity. Among this class of molecules, the spiro-lactams subclass stands out, being extensively explored due to its bioactivity and utility in a variety of scientific fields such as drug design and organic synthesis. Given the recognition of spirocyclic lactams’ broad potential, several efforts have been en...
Spiro-β-lactam BSS-730A Displays Potent Activity against HIV and Plasmodium
Bártolo, Inês; Santos, Bruna S; Fontinha, Diana; Machado, Marta; Francisco, Denise; Sepodes, Bruno; Rocha, João; Mota-Filipe, Hélder; Pinto, RuiThe high burden of malaria and HIV/AIDS prevents economic and social progress in developing countries. A continuing need exists for development of novel drugs and treatment regimens for both diseases in order to address the tolerability and long-term safety concerns associated with current treatment options and the emergence of drug resistance. We describe new spiro-β-lactam derivatives with potent (nM) activit...
Synthesis of Novel Chiral Spiroisoxazolidine‐β‐Lactams from 6‐Alkylidenepenicil...
Alves, Américo J. S.; Melo, Teresa M. V. D. Pinho eThe synthesis of a library of 6‐alkylidene‐β‐lactams, derived from 6‐aminopenicillanic acid is reported. The 1,3‐dipolar cycloaddition of these 6‐alkylidenepenicillanates with nitrones was explored as an approach to synthesize novel chiral spiroisoxazolidine‐β‐lactams. The reported methodology, which involves the generation of three new consecutive stereogenic centers, proved to be regio‐ and stereoselective, l...
Spiro-Lactams as Novel Antimicrobial Agents
Alves, Américo J. S.; Alves, Nuno G.; Caratão, Cátia C.; Esteves, Margarida I. M.; Fontinha, Diana; Bártolo, Inês; Soares, Maria I. L.Introduction: Structural modulation of previously identified lead spiro-β-lactams with antimicrobial activity was carried out. Objective: The main objective of this work was to synthesize and evaluate the biological activity of novel spiro-lactams based on previously identified lead compounds with antimicrobial activity. Methods: The target chiral spiro-γ-lactams were synthesized through 1,3-dipolar cycloadditi...