3-Aza-6,8-dioxabicyclo[3.2.1]octanes as new enantiopure heteroatom-rich tropane-like ligands of human dopamine transporter

Cini, Nicoletta; Danieli, Elisa; Menchi, Gloria; Trabocchi, Andrea; Bottoncetti, Anna; Raspanti, Silvia; Pupi, Alberto; Guarna, Antonio

doi:10.1016/j.bmc.2006.04.019

Cited by 6 publications

(1 citation statement)

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“…All BTAas are derived from tartaric acid and one amino acid (Guarna et al, 1999; Trabocchi et al, 2002, 2003; Cini et al, 2006; Machetti et al, 2007). BTAas can be classified in two ways: according to the absence/presence of a double bonded Oxygen or Sulfur (Scaffold B, A, and C, Figure 1A) (Guarna et al, 1999), or according to the chemical reactants used to synthesize them (Figure 1B) (Machetti et al, 2007).…”

Section: Resultsmentioning

confidence: 99%

Relations between Effects and Structure of Small Bicyclic Molecules on the Complex Model System Saccharomyces cerevisiae

et al. 2017

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The development of compounds able to modify biological functions largely took advantage of parallel synthesis to generate a broad chemical variance of compounds to be tested for the desired effect(s). The budding yeast Saccharomyces cerevisiae is a model for pharmacological studies since a long time as it represents a relatively simple system to explore the relations among chemical variance and bioactivity. To identify relations between the chemical features of the molecules and their activity, we delved into the effects of a library of small compounds on the viability of a set of S. cerevisiae strains. Thanks to the high degree of chemical diversity of the tested compounds and to the measured effect on the yeast growth rate, we were able to scale-down the chemical library and to gain information on the most effective structures at the substituent level. Our results represent a valuable source for the selection, rational design, and optimization of bioactive compounds.

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Section: Resultsmentioning

confidence: 99%

Relations between Effects and Structure of Small Bicyclic Molecules on the Complex Model System Saccharomyces cerevisiae

et al. 2017

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Palladium-Catalyzed sp2 C–N Bond Forming Reactions: Recent Developments and Applications

Lemen

Wolfe

2012

Amination and Formation of Sp2 C-N Bonds

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Singular value decomposition analysis of the torsional angles of dopamine reuptake inhibitor GBR 12909 analogs: effect of force field and charges

et al. 2010

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Three-dimensional quantitative structure-activity relationship (3D-QSAR) analysis of large, flexible molecules, such as the dopamine reuptake inhibitor GBR 12909 (1), is complicated by the fact that they can take on a wide range of closely-related conformations. The first step in the analysis is to classify the conformers into groups. Over 600 conformers each of a piperazine (2) and piperidine (3) analog of 1 were generated by random search conformational analysis using the Merck Molecular Force Field (MMFF94). Singular value decomposition (SVD) was used to group the conformers of 2 and 3 by the similarity of their non-ring torsional angles. SVD uncovered subtle differences in their conformer populations due to that fact that the conformers separate along different principal components, and ultimately to the fact that different torsional angles are the chief contributors to these components. The results were compared to our previous SVD analysis (Fiorentino, et al., Journal of Computational Chemistry, 2006, 27, 609-620) of conformer populations of 2 and 3 generated by the Tripos force field and Gasteiger-Hückel charges. Except for the dominant contribution of angle B3 to principal component 8 seen with both force fields, the angles which are chiefly responsible for the grouping of the conformers of 2 and 3 are different with both force fields. This illustrates that SVD is useful in identifying unique groupings of conformers in large data sets of flexible molecules-a first step in selecting representative conformers for 3D-QSAR modeling studies.

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3-Aza-6,8-dioxabicyclo[3.2.1]octanes as new enantiopure heteroatom-rich tropane-like ligands of human dopamine transporter

Cited by 6 publications

References 50 publications

Relations between Effects and Structure of Small Bicyclic Molecules on the Complex Model System Saccharomyces cerevisiae

Relations between Effects and Structure of Small Bicyclic Molecules on the Complex Model System Saccharomyces cerevisiae

Palladium-Catalyzed sp2 C–N Bond Forming Reactions: Recent Developments and Applications

Singular value decomposition analysis of the torsional angles of dopamine reuptake inhibitor GBR 12909 analogs: effect of force field and charges

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