Giordano Lesma

University of Milan

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Alessandra Silvani

University of Milan

146

Bruno Danieli

University of Milan

136

Giovanni Palmisano

University of Insubria

Daniele Passarella

University of Milan

Alessandro Sacchetti

Politecnico di Milano

Giulia Rainoldi

University of Milan

Renata Riva

University of Genoa

Stefano Tollari

University of Insubria

Mattia Stucchi

University of Modena and Reggio Emilia

Sergio Riva

Istituto di Chimica Biomolecolare

Cooperative Institutions

University of Milan

124

Mylan (Switzerland)

Mylan (South Africa)

National Interuniversity Consortium of Materials Science and Technology

Politecnico di Milano

Milano University Press

University of Padua

Institute of Chemistry of Molecular Recognition

Institute of Molecular Science and Technologies

Istituto di Chimica Biomolecolare

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Covalent Nucleoside Adducts of Aspidosperma Alkaloids

Nucleosides and Nucleotides (1991)

Bruno Danieli Giordano Lesma Giovanni Palmisano Daniele Passarella B. Pyuskyulev

Abstract In vitro reaction of 17-OH tabersonine 2a and its 11-OMe analogue 2b with adenine, tri-O-acetyl adenosine, -guanosine and -cytidine under mild conditions, results in covalent adducts by electrophilic attack of reactive C-17 position of the alkaloids on the exocyclic nitrogen.

Cytidine

Derivative (finance)

10.1080/15257779108043053

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Citations (1)

The Photochemical Behavior of Colchicone and Thiocolchicone

Photochemistry and Photobiology (2000)

Luca Bussotti Maria Valeria D’Auria Paolo Foggi Giordano Lesma Roberto Righini

The irradiation of colchicone 5 led to the formation of lumicolchicone 7. The same reaction cannot be obtained by using thiocolchicone 6 as substrate. Transient absorption spectroscopy of colchicone and beta-lumicolchicone showed that probably the photoisomerization occurred on colchicone in its first excited singlet state. The spectroscopic data are in agreement with the hypothesis that lumicolchicone was generated in the ground state from the S1 state of colchicone without the presence of any intermediate. Semiempirical calculations on colchicone and thiocolchicone showed that the highest single occupied molecular orbital and the lowest unoccupied molecular orbital of the singlet excited colchicone can give a disrotatory ring closure to 7, while thiocolchicone cannot give the same type of process.

Conrotatory and disrotatory

Singlet fission

10.1562/0031-8655(2000)071<0029:tpboca>2.0.co;2

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Citations (9)

Synthesis of Enantiopure Diamine Ligands Related to Sparteine, via Scandium Triflate‐Catalyzed Imino Diels—Alder Reactions.

ChemInform (2002)

Bruno Danieli Giordano Lesma Daniele Passarella Paola Piacenti Alessandro Sacchetti

Abstract For Abstract see ChemInform Abstract in Full Text.

Enantiopure drug

Scandium

Trifluoromethanesulfonate

Sparteine

10.1002/chin.200252207

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ChemInform Abstract: Multicomponent Access to Novel Dihydroimidazo[1′,5′:1,2]pyrido[3,4‐b]indol‐2‐ium Salts and Indoles by Means of Ugi/Bischler—Napieralski/Heterocyclization Two Step Strategy.

ChemInform (2014)

Alessandra Silvani Giordano Lesma Sergio Crippa Vito Vece

10.1002/chin.201445174

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Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine

Tetrahedron Asymmetry (2004)

Alessio Barilli Francesca Belinghieri Daniele Passarella Giordano Lesma Sergio Riva

Kinetic resolution

10.1016/j.tetasy.2004.06.056

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Citations (44)

Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-Heteroarylindoles

Synthesis (2010)

Alessandra Silvani Marco Baroni Giordano Lesma Letizia Puleio Alessandro Sacchetti

Corrected by: Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-HeteroarylindolesSynthesis 2011; 2011(02): 352-352DOI: 10.1055/s-0030-1258360

10.1055/s-0030-1258289

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Citations (4)

Total Enantioselective Synthesis of (‐)‐Cytisine.

ChemInform (2004)

Bruno Danieli Giordano Lesma Daniele Passarella Alessandro Sacchetti Alessandra Silvani

10.1002/chin.200426180

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Citations (3)

Phytosterol and γ-Oryzanol Conjugates: Synthesis and Evaluation of their Antioxidant, Antiproliferative, and Anticholesterol Activities

Journal of Natural Products (2018)

Giordano Lesma Andrea Luraghi Teodora Bavaro Roberta Bortolozzi Giulia Rainoldi

Fifteen new multifunctional conjugates were designed and synthesized by chemically linking the steroidal framework of natural occurring γ-oryzanol and γ-oryzanol-derived phytosterols to a wide range of bioactive natural compounds (fatty acids, phenolic acids, amino acids, lipoic acid, retinoic acid, curcumin, and resveratrol). Starting from γ-oryzanol, which is the main component of rice bran oil, this study was aimed at assessing if the conjugation strategy might enhance some γ-oryzanol bioactivities. The antioxidant activity was evaluated through three different mechanisms, namely, DPPH-scavenging activity, metal-chelating activity, and β-carotene-bleaching inhibition. Measurement of the in vitro cell growth inhibitory effects on three different human cancer cellular lines was also carried out, and the potential hypocholesterolemic effect was studied. Compounds 10 and 15 displayed an improved antioxidant activity, with respect to that of γ-oryzanol. Compounds 2, 6, and 12 exerted an antiproliferative activity in the low micromolar range against HeLa and DAOY cells (GI50 < 10 μM). As for the claimed hypocholesterolemic effect of γ-oryzanol, none of the synthesized compounds inhibited the 3-hydroxy-3-methylglutaryl-coenzyme A reductase, a key enzyme in cholesterol biosynthesis.

Phytosterol

Rice bran oil

HeLa

Coenzyme A

10.1021/acs.jnatprod.8b00465

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Citations (27)

ChemInform Abstract: DYE‐SENSITIZED PHOTOOXYGENATION OF THE ASPIDOSPERMA ALKALOIDS VINCADIFFORMINE AND TABERSONINE. A NEW, CONVENIENT APPROACH TO VINCAMINE

Chemischer Informationsdienst (1982)

Luisella Calabi Bruno Danieli Giordano Lesma Giovanni Palmisano

Abstract Das bei der Photooxidation von (‐)‐Vincadifforniin (Ia) zu dem Oxoindol (III) als Zwischenprodukt auftretende Hydroperoxid (II) wird in Gegenwart eines Sensibilisators und von Thiosulfat als Reduktionsmittel in einer stereoselektiv verlaufenden Reaktion als Hydroxyester (IVa) abgefangen.

Photooxygenation

Aspidosperma

10.1002/chin.198237326

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ChemInform Abstract: MICROBIAL HYDROXYLATION OF HETEROYOHIMBINE ALKALOIDS

Chemischer Informationsdienst (1984)

Giordano Lesma Giovanni Palmisano Stefano Tollari Pola Ame P. Martelli

10.1002/chin.198411340

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Citations (0)