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Arena G.,University of Siena | Barreca G.,Chemessentia Srl | Carcone L.,Chemessentia Srl | Cini E.,University of Siena | And 7 more authors.
Advanced Synthesis and Catalysis | Year: 2013

The novel rhodium complex [Rh(S)-Phanephos(cod)]-catalyzed hydrogenation of disubstituted (E)-enol acetate carboxylic acids is reported. The catalytic cycle works under 30 bar of hydrogen under conventional heating giving different 3-acetoxy-2,3-disubstituted carboxylic acids with ee ≥90%. Hydrogenation occurred also under microwave dielectric heating without eroding the enantioselectivity but improving the overall efficiency of the process. With microwaves, hydrogen pressure and reaction time required for complete hydrogenation dropped to 5 bar and 30 min, respectively. The best performance of this catalyst under microwave irradiation was TON 100, TOF 196 h-1 with ee 99% on a 6-g scale. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Riva R.,University of Genoa | Banfi L.,University of Genoa | Castaldi G.,Chemessentia Srl | Ghislieri D.,Chemessentia Srl | And 4 more authors.
European Journal of Organic Chemistry | Year: 2011

A very short and cost-effective synthesis of the commercial drug paliperidone has been achieved starting from its parent compound risperidone, through a thoroughly optimized oxidation with air under basic conditions. A very short and cost-effective synthesis of the commercial drug paliperidone (1) has been achieved starting from its parent compound risperidone, through a thoroughly optimized oxidation with air under basic conditions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Cavallo G.,Polytechnic of Milan | Marras G.,Chemessentia Srl | Metrangolo P.,Polytechnic of Milan | Pilati T.,Polytechnic of Milan | Terraneo G.,Polytechnic of Milan
Acta Crystallographica Section E: Structure Reports Online | Year: 2013

In the crystal structure of the title compound, C8F16I2·C14H8N2, the molecules form infinite chains parallel to [2-11] through two symmetry-independent C - I⋯N halogen bonds (XBs). As commonly found, the perfluoroalkyl molecules segregate from the hydrocarbon ones, forming a layered structure. Apart from the XBs, the only contact below the sum of van der Waals radii is a weak H⋯F contact. The topology of the network is a nice example of the paradigm of the expansion of ditopic starting modules; the XB leads to the construction of infinite supramolecular chains along [2-11] formed by alternating XB donors and acceptors. © 2013 Cavallo et al.


Hugentobler K.G.,University of Manchester | Hugentobler K.G.,Albert Ludwigs University of Freiburg | Sharif H.,University of Manchester | Rasparini M.,Chemessentia Srl. | And 3 more authors.
Organic and Biomolecular Chemistry | Year: 2016

Three complementary biocatalytic routes were examined for the synthesis of the cyclopropyl amine (1R,2S)-2, which is a key building block for the anti-thrombotic agent ticagrelor 1. By employing either a ketoreductase, amidase or lipase biocatalyst, the key building blocks for synthesis of the amine 2 were obtained in 99.9, 92.5 and 46.3 ee, respectively. © 2016 The Royal Society of Chemistry.


Donadio L.G.,National Institute of Industrial Technology | Galetti M.A.,National Institute of Industrial Technology | Giorgi G.,University of Siena | Rasparini M.,Chemessentia SRL | And 2 more authors.
Journal of Organic Chemistry | Year: 2016

Using the reaction between phenylacetaldehyde and nitrostyrene catalyzed by pyrrolidine as a simple model, we have studied the diastereochemical outcome of the organocatalytic Michael reactions between benzylic aldehydes and nitrostyrenes. We found that the anti adduct was obtained in high yield and diastereoselection as was demonstrated by the X-ray structure of the product. In situ NMR studies showed a different reaction pathway when compared to aliphatic aldehydes that yield the syn adduct as major isomer. © 2016 American Chemical Society.


Cevasco G.,University of Genoa | Cevasco G.,CNR Institute of Neuroscience | Piatek A.M.,University of Genoa | Piatek A.M.,Chemessentia SRL | Thea S.,University of Genoa
Clinica Chimica Acta | Year: 2014

A simple and sensitive new method for the determination of d-3-hydroxybutyric acid (D-3-HBA) in human plasma after derivatization is described. The proposed method is based on the reaction of (2S)-2-amino-3-methyl-1-[4-(7-nitro-benzo-2,1,3-oxadiazol-4-yl)-piperazin-1-yl]-butan-1-one (NBD-PZ-Val) with D-3-HBA in the presence of O-(7-azobenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) and N-ethyldiisopropylamine (DIEA) to produce a fluorescent derivative. The formed derivative was monitored fluorimetrically at λex=489nm and λem=532nm. The HPLC analysis was carried out by use of a C18 analytical column (Synergy Hydro 150mm×3mm, i.d., 4μm) with a binary gradient elution program of 0.1% aqueous trifluoroacetic acid versus methanol. The method showed satisfactory linearity (r2=0.9997) in the range from 20 to 500μmol/L. The limit of detection (LOD) of the method was 7.7μmol/L, while the limit of quantitation (LOQ) was 25.8μmol/L. The analytical method was successfully applied to human plasma samples from normal healthy subjects. © 2013 Elsevier B.V.


Moni L.,University of Genoa | Banfi L.,University of Genoa | Basso A.,University of Genoa | Carcone L.,Chemessentia Srl | And 2 more authors.
Journal of Organic Chemistry | Year: 2015

Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir. © 2015 American Chemical Society.


PubMed | University of Genoa and Chemessentia Srl
Type: Journal Article | Journal: The Journal of organic chemistry | Year: 2015

Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir.


Fontana E.,Accelera S.r.l | Pignatti A.,Accelera S.r.l | Venegoni S.,Chemessentia S.r.l. | Bray M.A.,Drugs for Neglected Diseases Initiative DNDi CH
Journal of Labelled Compounds and Radiopharmaceuticals | Year: 2011

The preparation of deuterium labeled fexinidazole, a 5-nitroimidazole drug candidate for the treatment of Human African Trypanosomiasis, and its two main metabolites (fexinidazole sulfoxide and fexinidazole sulfone) for use as internal standards for liquid chromatography-mass spectrometry are reported. Additionally, the synthesis of a 14 C-labeled version of fexinidazole for absorption, distribution, metabolism, and excretion studies is also described via a five-step procedure starting from commercially available potassium [ 14 C]cyanide. Copyright © 2011 John Wiley & Sons, Ltd.

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