Synthesis of enantiopure cyclobutane amino acids and amino alcohols

Balo, Carmen; Caamaño, Olga; Fernández, Fernando Nieto; López, Carmen

doi:10.1016/j.tetasy.2005.06.030

Cited by 6 publications

(4 citation statements)

References 19 publications

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“…The (S,R)-(512) is available by Curtius rearrangement to give the keto-acid (513) and subsequent haloform reaction [361]. Similar syntheses of (512) have also been reported from (S)-verbenone [362] and ( þ )-(R)-a-pinene [363]. The highly stereoselective conjugate addition of nitromethane to a,b-unsaturated cyclobutyl esters derived from (À)-(S)-verbenone furnishes 3-substituted cyclobutyl gabapentin analogs [364].…”

Section: Cyclobutyl G-amino Acidssupporting

confidence: 52%

Synthesis of γ‐Aminobutyric Acid Analogs

Hanrahan

Johnston

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Section: Cyclobutyl G-amino Acidssupporting

confidence: 52%

Synthesis of γ‐Aminobutyric Acid Analogs

Hanrahan

Johnston

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…On the other hand, the second group of compounds (the uridine analogues 9b, 12c and 15d ) were constructed on the aminoalcohol 7b ,44 10c 45 and 13d by condensation with 3‐ethoxy‐2‐propenoyl isocyanate46 and cyclization of the urea 8b with conventional acidic conditions (see Schemes 2, 3 and…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the second group of compounds (the uridine analogues 9b, 12c and 15d) were constructed on the aminoalcohol 7b, [44] 10c [45] and 13d by condensation with 3-ethoxy-2-propenoyl isocyanate [46] and cyclization of the urea 8b with conventional acidic conditions (see Schemes 2, 3 and 4). In a previous work, our research group synthesized 1(N)-homocarbanucleosides in which the double bond of the cyclopentene ring of carbovir and abacavir was replaced with a pyridazine.…”

Section: Discovery Of Novel Carbonucleoside Anticancer Compoundsmentioning

confidence: 99%

“…The resulting mixture was refluxed with vigorous stirring for a further 30 min at room temperature for 3 h, and then left to settle. A sample of the supernatant (2.5 mL, theoretically containing 1.03 mmol of 3-ethoxypropenoyl isocyanate) was transferred to a dropping funnel and added dropwise under argon to a solution of 7b [44] (0.10 g, 0.77 mmol) in dry DMF (4 mL) at À15 8C. The resulting mixture was left for 1 h to reach room temperature and was then stirred overnight and concentrated under reduced pressure (oil pump) at a temperature below 40 8C.…”

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confidence: 99%

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Design, Synthesis, and Evaluation of Antineoplastic Activity of Novel Carbocyclic Nucleosides

Helguera

Rodríguez‐Borges

Caamaño

et al. 2010

Molecular Informatics

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Cancer is the leading cause of death among men and women under age 85. Every year, millions of individuals are diagnosed with cancer. But finding new drugs is a complex, expensive, and very time-consuming task. Over the past decade, the cancer research community has begun to address the in silico modeling approaches, such as Quantitative Structure-Activity Relationships (QSAR), as an important alternative tool for targeting potential anticancer drugs. With the compilation of a large dataset of nucleosides synthesized in our laboratories, or elsewhere, and tested in a single cytotoxic assay under the same experimental conditions, we recognized a unique opportunity to attempt to build predictive QSAR models. Early efforts with 2D classification models built from part of this dataset were very encouraging. Here we report a further detailed evaluation of classification models to flag potential anticancer activities derived from a variety of 3D molecular representations. A quantitative 3D-model model that discriminates anticancer compounds from the inactive ones was attained, which allowed the correct classification of 82 % of compounds in such a large and diverse dataset, with only 5 % of false inactives and 11 % of false actives. The model developed here was then used to select and design a new series of nucleosides, by classifying beforehand them as active/inactive anticancer compounds. From the compounds so designed, 22 were synthesized and evaluated for their inhibitory effects on the proliferation of murine leukemia cells (L1210/0), of which 86 % were well-classified as active or inactive, and only two were false actives, corroborating the good predictive ability of the present discriminant model. The results of this study thus provide a valuable tool for the design of novel potent anticancer nucleoside analogues.

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Rearrangements of Hydroxylamines, Oximes and Hydroxamic Acids

Pereira

Santos²

2010

Patai's Chemistry of Functional Groups

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Introduction The [3,3]‐Sigmatropic Rearrangements The [2,3]‐Sigmatropic Rearrangements The Dyotropic Rearrangements The B amberger Rearrangements The B eckmann Rearrangements The N eber Rearrangements The L ossen Rearrangement Other Rearrangements

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Synthesis of enantiopure cyclobutane amino acids and amino alcohols

Cited by 6 publications

References 19 publications

Synthesis of γ‐Aminobutyric Acid Analogs

Synthesis of γ‐Aminobutyric Acid Analogs

Design, Synthesis, and Evaluation of Antineoplastic Activity of Novel Carbocyclic Nucleosides

Rearrangements of Hydroxylamines, Oximes and Hydroxamic Acids

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