Article
Biochemistry & Molecular Biology
Jonathan Elie, Corinne Fruit, Thierry Besson
Summary: This paper describes a convenient sequential one-pot approach for the synthesis of a series of 14 pyrazolo[1,5-a][1,3,5]triazines, with advantages in terms of yields, reaction times, and convenient gram scale synthesis compared to traditional methods. The combination of efficient heating using dielectric microwave heating and sequential one-pot reactions eliminates the need for laborious work-up and purification of intermediate compounds, allowing for sustainable synthesis processes.
Article
Chemistry, Organic
Baofu Zhu, Jiaming He, Kai Zou, Anquan Li, Chen Zhang, Jiaji Zhao, Hua Cao
Summary: This study established a three-component reaction catalyzed by base, involving ynals, isocyanates, amines, and alcohols. The strategy enables a wide range of substrates and provides a simple process for the preparation of diverse pyridine derivatives with good yields and high regioselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Dmytro S. Radchenko, Vasyl S. Naumchyk, Igor Dziuba, Andrii A. Kyrylchuk, Kateryna E. Gubina, Yurii S. Moroz, Oleksandr O. Grygorenko
Summary: The three-component one-pot approach described in this study successfully synthesized unsymmetrical 1,3,5-trisubstituted-1,2,4-triazoles, with a high success rate of 81%. The methodology shows great potential for generating a large number of REAL compounds, some of which meet lead-likeness criteria and can be valuable in medicinal chemistry.
MOLECULAR DIVERSITY
(2022)
Article
Chemistry, Multidisciplinary
Muhammad Syafiq Bin Shahari, Edward R. T. Tiekink, Anton V. Dolzhenko
Summary: A new method for the synthesis of bis(1,3,5-triazine-2,4-diamines) has been developed using a one-pot multicomponent approach. The method involves the acid-catalyzed reaction of cyanoguanidine with amines and aldehydes, followed by dehydrogenative aromatization of the dihydrotriazine intermediates upon heating with alkali. The microwave-assisted method allows fast and convenient synthesis of diverse bis(1,3,5-triazine-2,4-diamines).
Article
Chemistry, Multidisciplinary
Muhammad Idham Darussalam Mardjan, Muhamad Fadhly Hariadi, Chessy Rima Mustika, Hamzah Shiddiq Saifurofi', Eko Sri Kunarti, Bambang Purwono, Laurent Commeiras
Summary: A library of 3-substituted isoindolinones was synthesized using one-pot reaction under ultrasound irradiation. The synthesized compounds showed moderate to strong antiplasmodium activities and low toxicity effects, meeting the drug-likeliness requirements. Among them, four derivatives were identified as potential antiplasmodium candidates.
Article
Chemistry, Multidisciplinary
Yong Tang, Kaifu Zhang, Yuelin Xu, Jinglin Ma, Hanqing Xie, Hongquan Zhang, Yanmin Jiang, Rui Zhao, Lei Wang
Summary: A green and efficient method for the construction of functionalized 2,3-dihydrothiophene derivatives in water was reported. Novozym 435 demonstrated remarkable catalytic activity in the four-component reaction of aldehydes, malonitrile or ethyl cyanoacetate, 1,3-thiazolidinedione, and amines, resulting in excellent product yields. Furthermore, the catalyst could be reused for multiple cycles.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Mohammad Taghi Nazeri, Ahmad Shaabani, Behrouz Notash
Summary: An efficient green sonochemical approach was developed for the synthesis of small-ring heterocycles containing pyrrole and pyrazole, resulting in fully substituted pyrroles connected to pyrazole scaffolds with high chemoselectivity. The reaction exhibited high atom economy and step economy, creating four new bonds including two C-N and two C-C bonds in a single operation. The synthesized compounds showed interesting fluorescence features, indicating potential applications in clinical diagnostics and biomedical research.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Vani Verma, Laurel L. Schafer
Summary: This article describes a one-pot general method for the selective synthesis of less explored/challenging patterns of tri-substituted pyridines. Hydroamination of alkynes with commercially available N-triphenylsilylamine generates N-silylenamines, which, upon reaction with alpha, beta-unsaturated carbonyl compounds and subsequent oxidation, provide 25 examples of selectively substituted 2,4,5-, 2,3,4-, 3,4,5-, 2,3,5-, and 2,3,6-trisubstituted pyridines in up to 78% yield. The reaction exhibits high functional group compatibility and offers an expeditious and general approach for the assembly of selectively substituted trisubstituted pyridine derivatives. The robustness and practicality of the reaction have been demonstrated in a gram-scale reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Vani Verma, Laurel L. Schafer
Summary: This paper describes a selective synthesis method for tri-substituted pyridines. The hydroamination of alkynes with commercially available N-triphenylsilylamine generates N-silylenamines, which upon reaction with alpha, beta-unsaturated carbonyl compounds and subsequent oxidation, produces selectively substituted 2,4,5-, 2,3,4-, 3,4,5-, 2,3,5-, and 2,3,6-trisubstituted pyridines in up to 78% yield. The reaction shows high functional group compatibility and provides an efficient and general approach for selectively assembling trisubstituted pyridine derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Polymer Science
Burcu Alkan, Ozgun Daglar, Serter Luleburgaz, Begum Gungor, Ufuk Saim Gunay, Gurkan Hizal, Umit Tunca, Hakan Durmaz
Summary: A novel one-pot cascade reaction was proposed for the synthesis and simultaneous modification of polyesters, utilizing the Passerini three-component reaction. The study emphasized the significance of temperature in achieving high molecular weight polymers and efficient reactions.
Article
Chemistry, Multidisciplinary
Chiara Portolani, Giovanni Centonze, Sara Luciani, Andrea Pellegrini, Paolo Righi, Andrea Mazzanti, Alessia Ciogli, Andrea Sorato, Giorgio Bencivenni
Summary: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Faranak Manteghi, Fatemeh Zakeri, Owen James Guy, Zari Tehrani
Summary: A chromium-containing metal-organic framework MIL-101 was effectively used as a heterogeneous catalyst for the solvent-free synthesis of 2,4,5-trisubstituted imidazoles, showing advantages such as high efficiency, reusability, and ease of isolation. The catalytic reaction achieved a high yield in a short time, making it a promising alternative to other catalysts.
Review
Polymer Science
Saad Shaaban, Hany M. Abd El-Lateef, Mai M. Khalaf, Mohamed Gouda, Ibrahim Youssef
Summary: The one-pot multicomponent synthetic strategy of organoselenium compounds, as an alternative and robust method, has shown potential advancements.
Article
Chemistry, Organic
Muhammad Syafiq Bin Shahari, Ahmad Junaid, Edward R. T. Tiekink, Anton Dolzhenko
Summary: A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed using microwave irradiation in a one-pot manner. The targeted compounds showed potent antileukemic activity, indicating the potential biological activity of this method.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Subhankar Paul, Sharmistha Das, Bijeta Mitra, Gyan Chandra Pariyar, Pranab Ghosh
Summary: A green, novel, and eco-efficient synthetic route for highly substituted bio-active pyrrolidine-2-one derivatives was demonstrated using beta-cyclodextrin as a catalyst. This protocol utilizes water-ethanol solvent medium at room temperature and allows for one-pot three-component synthesis of a wide range of highly functionalized bio-active heterocyclic pyrrolidine-2-one moieties from readily available aldehydes and amines.
Article
Biochemical Research Methods
Zoia Shedania, Rusudan Kakava, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2018)
Article
Pharmacology & Pharmacy
Nina Bono, Chiara Pennetta, Aurora Sganappa, Elisa Giupponi, Francesco Sansone, Alessandro Volonterio, Gabriele Candiani
INTERNATIONAL JOURNAL OF PHARMACEUTICS
(2018)
Article
Biochemical Research Methods
Lia Bezhitashvili, Anna Bardavelidze, Antonina Mskhiladze, Mehmet Gumustas, Sibel A. Ozkan, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2018)
Article
Chemistry, Multidisciplinary
Nina Bono, Chiara Pennetta, Maria Cristina Belluci, Aurora Sganappa, Chiara Malloggi, Gabriella Tedeschi, Gabriele Candiani, Alessandro Volonterio
Article
Biochemical Research Methods
Zoia Shedania, Rusudan Kakava, Alessandro Volonterio, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2020)
Article
Chemistry, Applied
Maria Cristina Bellucci, Alessandro Sacchetti, Alessandro Volonterio
ACS COMBINATORIAL SCIENCE
(2019)
Article
Biochemical Research Methods
Salome Pantsulaia, Khatia Targamadze, Nana Khundadze, Qetevan Kharaishvili, Alessandro Volonterio, Michael Chitty, Tivadar Farkas, Bezhan Chankvetadze
JOURNAL OF CHROMATOGRAPHY A
(2020)
Review
Infectious Diseases
Maria Cristina Bellucci, Alessandro Volonterio
Article
Biochemical Research Methods
Chiara Pennetta, Nina Bono, Federica Ponti, Maria Cristina Bellucci, Fiorenza Viani, Gabriele Candiani, Alessandro Volonterio
Summary: This study describes the design and synthesis of a novel class of aminoglycoside (AG)-based multifunctional vectors with high transfection efficiency and noticeable antibacterial properties. The results demonstrate excellent DNA condensation ability, good transfection performance with negligible cytotoxicity, as well as strong potential as antimicrobial agents.
BIOCONJUGATE CHEMISTRY
(2021)
Article
Chemistry, Organic
Eliana Lo Presti, Alessandro Volonterio, Monica Sani
Summary: This work reports the first synthesis of the complex amino acid labionin in a fully orthogonally protected and stereopure form. The structure incorporates five orthogonal protecting groups and three stereogenic centers, assembled using thia-Michael addition and electrophilic azidation. The successful synthesis is expected to enable the solid phase synthesis of both natural and synthetic analogues of labyrinthopeptins.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Gaetano Cristina, Carlo Castellano, Fiorella Meneghetti, Matteo Mori, Francesco Secundo, Fiorenza Viani, Alessandro Sacchetti, Alessandro Volonterio
Summary: This study presents the synthesis of a collection of enantiomerically pure, systematically substituted hydantoins as structural privileged universal mimetic scaffolds. The synthesis relies on a selective condensation/cyclization process between isocyanates and aspartic acid diesters, followed by hydrolysis/coupling reactions with amines. Conformational studies showed that the hydantoin-based peptidomimetics are capable of projecting their substituents in positions superimposable to common protein secondary structures.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Carola Romani, Paola Gagni, Mattia Sponchioni, Alessandro Volonterio
Summary: In this study, we successfully functionalized PAMAM G2 and PAMAM G4 with fluorinated arginine-based building blocks, resulting in a novel PAMAM-based gene delivery vector. The conjugates showed improved binding capacity to plasmid DNA, reduced cytotoxicity, and enhanced gene transfection efficiency compared to undecorated PAMAM dendrimers. These findings are of great importance for gene delivery research and also have the potential for future application in F-19 magnetic resonance imaging.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Emerenziana Ottaviano, Silvia Ancona, Elisa Borghi, Alessandro Volonterio
Summary: Three model hydantoin-based universal peptidomimetics were designed, synthesized, and investigated for their conformation and antibacterial activity. The results demonstrated that these compounds could be promising antibiotics to combat drug resistance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Alessio M. Caramiello, Maria Cristina Bellucci, Emerenziana Ottaviano, Silvia Ancona, Elisa Borghi, Alessandro Volonterio
Summary: In this study, three model hydantoin-based universal peptidomimetics were designed, synthesized, and investigated for their antibacterial activities against Gram-positive and Gram-negative bacteria strains. The results demonstrated that these compounds could potentially serve as promising antibiotics to combat emerging drug resistance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Kaivin Hadidi, Maria Cristina Bellucci, Sergio Dall'Angelo, Alasdair Leeson-Payne, Justin J. Rochford, Jeffery D. Esko, Yitzhak Tor, Alessandro Volonterio
Summary: Guanidinoglycosides are non-cytotoxic molecular transporters capable of delivering high molecular weight bioactive cargos into cells at low nanomolar concentrations. The use of a stable guanidinoneomycin derivative armed with a highly specific maleimide moiety allows for efficient bioconjugation through thiol-maleimide click chemistry, expanding the field of application for these delivery vehicles.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)