Lígia M. Rodrigues

Tacrine and its analogues impair mitochondrial function and bioenergetics : a lipidomic analysis in rat brain

J. Neurochem. (2012) 120, 993–1013.

Heterocyclic Synthesis with Nitriles: Synthesis of Pyrazolopyrimidine and Pyrazolopyridine Derivatives

Abstract The reaction of N 1-substituted-5-amino-4-cyanopyrazoles with malononitrile and diethylmalonate occurs with formation of 6-substituted pyrazolo[3,4-d]pyrimidines, and pyrazolo[3,4-b]pyridines respectively. The structures of the products and conceivable mechanisms are discussed.

Synthesis of novel benzofurocoumarin analogues and their anti-proliferative effect on human cancer cell lines

The synthesis of five new tetracyclic benzofurocoumarin (benzopsoralen) analogues is described. Their inhibitory effects on the growth of three human tumor cell lines (MDA MB 231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma) were evaluated, and discussed in terms of structure-activity relationship.

Synthesis of novel derivatives of 4-amino-3,5-dicyanopyrazole

Diazotisation of substituted arylamines followed by reaction with malononitrile gave substituted arylazomalononitriles. Cyclisation of these intermediates with chloroacetonitrile and triethylamine, as base, gave the corresponding new aminodicyanopyrazoles, in 22–80% yields.

Synthesis of Tacrine Analogs Derived from N-Aryl-5-amino-4-cyanopyrazoles

Abstract Synthesis of 11 tacrine analogs derived from N-aryl-5-amino-4-cyanopyrazoles, by a Friedländer type reaction, is described. Their structures were confirmed by 1H and 13C NMR spectroscopy, elemental analysis, and/or mass spectrometry.

Synthesis of novel psoralen analogues and their in vitro antitumor activity

New tetracyclic benzofurocoumarin (benzopsoralen) analogues were synthesized and their inhibitory effect on the growth of tumor cell lines was evaluated. The human tumor cell lines used were MDA MB231 (breast adenocarcinoma), HeLa (cervix adenocarcinoma) and TCC-SUP (bladder transitional cell carcinoma). The in vitro antitumor activity of the new benzopsoralens was discussed in terms of structure-activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds in order to evaluate the potential of these compounds to interact with the heme group of the enzymes. The results have demonstrated that the linear compounds have the most pronounced activity against tumor cell lines and this might be related to the better accessibility that these compounds have to the active site in relation to the angular ones that have shown in the majority of the cases multiple binding poses in the active site of CYP2A6.

Synthesis of esters derived from 2,3,4-tri-O-benzyl-alpha-D-methylglucoside

FCT (Fundacao para a Ciencia e Tecnologia) and FEDER for financial support. The Bruker Avance III 400 spectrometer is part of the National NMR network and was purchased under the framework of the National Programme for Scientific Reequipment, contract REDE/1517/RMN/2005, with funds from POCI 2010 (FEDER) and (FCT). We are also grateful for research grant VZ MSMT- 0021627501, Czech Republic.

Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

Abstract The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole, and one tetrahydro-γ-carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1 to give three final products and with peracetylated 6-azido-6-deoxy-α-D-methylglucoside, giving the corresponding derivative of tetrahydro-γ-carboline. Supplemental materials are available for this article. Go to the publishers online edition of Synthetic Communications® to view the free supplemental file. GRAPHICAL ABSTRACT

Synthesis and structural aspects of some intermediates in furofuran lignan synthesis

The synthesis of some intermediates of furofuran lignans was accomplished by a chemical cyclisation reaction using N-ethylpiperidine hypophosphite and azobisisobutyronitrile. This reaction afforded the 5-exo-dig cyclic compound as the major product along with another isomeric cyclic compound which possess an endocyclic double bond. A brief discussion is presented to explain the formation of these isomeric cyclic compounds by a base-catalysed tautomerism mechanism. Some structural aspects are discussed based on nuclear magnetic resonance data.

Synthesis of 4-Amino-3,5-dicyano-arylpyrazoles, Part 2: Isolation and Characterization of By-Products

Abstract Reaction of (dicyanomethylidene-hydrazino)benzoic acids with chloroacetonitrile, under basic conditions, gave cyanomethyl-3-(7-amino-3,5-dicyano-1H-pyrazolo[4,3-d]pyrimidin-1-yl-benzoates and para-substituted cyanomethyl benzoates, in addition to the expected cyanomethyl 3-(4-amino-3,5-dicyano-1H-pyrazol-1-yl)-benzoates. GRAPHICAL ABSTRACT