Article
Chemistry, Multidisciplinary
Christopher W. Lamartina, Cassandra A. Chartier, Sumin Lee, Neel H. Shah, Tomislav Rovis
Summary: Here, a modular peptide ligation methodology is reported, which uses Rh(III) catalysis to couple dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner under mild conditions. The method shows excellent functional group tolerance and a large substrate scope, allowing for the construction of unnatural amino acid residues. This methodology is demonstrated in the synthesis of diastereomeric proteasome inhibitor analogs and the ligation of oligopeptides to construct a polypeptide with an unnatural residue.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang-gi Lee
Summary: The palladium-catalyzed divergent asymmetric synthesis of chiral spiro-furanindoline derivatives is described. The zwitterionic alkoxy pi-allyl Pd(II) intermediate, generated catalytically from vinyl ethylene carbonate (VEC), could undergo ligand-controlled enantio-and diastereoselective dipolar [3 + 2] spiroannulation with indole-based azadienes to afford the optically active spiro-furanindolines embedding an all-carbon quaternary stereocenter in high yields (up to 99%) with good to excellent stereoselectivities (up to 99% ee and up to >94:6 dr).
Article
Chemistry, Applied
Shreedhar Devkota, Muhammad Saeed Akhtar, Yong Rok Lee
Summary: This study explores the rhodium(III)-catalyzed sp(2)/sp(3) C-H activation/annulation of 2-arylquinazolin-4(3H)-ones with 3-methylmaleimides. Diversely functionalized isoindoloquinazolinones were obtained in good yields upon reaction with various maleimides. This Rh(III)-catalyzed protocol can be applied for the chemo- and diastereoselective synthesis of various polyheterocycles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jiagen Li, Ming Wang, Xuefeng Jiang
Summary: Stereoselective thioglycosylation via palladium-catalyzed allylic rearrangement was successfully achieved in this study, yielding various substituents on alpha-isomer thioglycosides. Additionally, a comprehensive series of aryl and benzyl thioglycosides were obtained through a combination of thiosulfates with glycals derived from different carbohydrates.
Article
Multidisciplinary Sciences
Leipeng Xie, Shenghao Wang, Lanlan Zhang, Lei Zhao, Chun Luo, Linping Mu, Xiuguang Wang, Chao Wang
Summary: The authors presented a method to add aryl and amino groups to alkenes regio- and diastereoselectively via nickel catalysis and a removable directing group. This method enables high levels of regio-, chemo- and diastereocontrol, and is compatible with broad substrate scope and high functional group tolerance. The utility of this method in site-selective modification of pharmaceutical agents has been demonstrated.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Poonam Shaifali, Poonam Sharma, Pushkar Mehara, Pralay Das
Summary: In this study, a heterogeneous and recyclable Pd@PS catalyst was utilized for the synthesis of potentially bioactive 2-(alkylamino/amino)-3-arylquinazolin-4(3H)-one analogues through a tandem addition and intramolecular aminocarbonylative cyclization approach. Various substituted 2-(alkylamino)-3-arylquinazolin-4(3H)-ones were selectively produced in good to excellent yields using amines as nucleophiles and oxalic acid as an ex-situ CO alternative. Furthermore, the gram scale applicability, diverse substrate scope, and high recyclability of the Pd@PS catalyst were significant achievements of this study.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Applied
Yu-Feng Liu, Gang-Ming Cao, Lei Chen, Ke Li, Xiao-Ling Lin, Xin-Xin Xu, Zhang-Gao Le, Guo-Ping Yang
Summary: We reported a method for the synthesis of 3,3'-disubstituted isobenzofuran-1(3H)-ones via the carbonyl difunctionalization of 2-acylbenzoic acids. The reaction yielded functionalized isobenzofuran-1(3H)-ones with a range of nucleophiles, achieving factual yield of 61-96%. The reaction was catalyzed by Cs0.5H2.5PW12O40 and water was the only by-product. The method enables the introduction of various functional groups to the isobenzofuran-1(3H)-one skeletons, offering opportunities for the synthesis of potential biologically active molecules.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Barry M. Trost, Zhijun Zuo
Summary: A novel Pd-0-catalyzed highly selective [3+2] spiroannulation reaction has been developed for rapid assembly of a new class of [5,5] spirocyclic carbo- and heterocycles. The regioselectivity of the reaction can be controlled by fine-tuning the Pd-pi-allyl intermediate, with excellent toleration of various coupling partners and enantioselectivities demonstrated through further transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Min Gao, Yinqiang Wang, Shuaijie Wu, Feier Ni, Cangzhu Hu, Feifei Jin, Jing Sun, Ying Han, Lei Wang
Summary: In this study, a novel and efficient strategy for the synthesis of dihydropyrazoles was presented. The synthesis involved the Pd-catalyzed carboamination reaction of alkenyl hydrazones with aryl triflates, leading to the simultaneous formation of C-C and C-N bonds. This methodology offers a practical and efficient approach for the synthesis of diversely aryl substituted dihydropyrazoles in good yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Minghui Qi, Muhammad Suleman, Jianwei Xie, Ping Lu, Yanguang Wang
Summary: We report a simple and efficient method for the selective C-H bond insertion of copper carbenes generated in situ from 4-diazo-1,4-dihydroisoquinolin-3-ones into beta-C(sp(2))-H bonds of N-sulfonyl enamides. This reaction yields a series of 4-(1,4,5,6-tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3(2H)-ones with good to excellent yields. The reaction benefits from its simple and mild reaction conditions, the use of a cheap catalyst, readily accessible starting materials, and a broad substrate scope.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Juba Ghouilem, Christine Tran, Nicolas Grimblat, Pascal Retailleau, Mouad Alami, Vincent Gandon, Samir Messaoudi
Summary: This study presents a novel Pd-catalyzed reaction for anomeric C-H bond activation, leading to the synthesis of elusive C-(hetero)aryl glycosides with exclusive α-selectivity.
Article
Chemistry, Organic
Garrit Wicker, Roland Schoch, Jan Paradies
Summary: The borane-catalyzed synthesis of dihydroquinoline-4-ones has been developed, with high yields and excellent diastereoselectivity. The reaction mechanism is investigated through kinetic, isotope labeling, and computational experiments.
Article
Chemistry, Organic
Shiji Xu, Qiang Wang, Jing Sun, Ying Han, Weiming Hu, Lei Wang, Chao-Guo Yan
Summary: In this study, Pd/Cu-catalyzed cascade Heck-type reactions between alkenyl halides and terminal alkynes have been developed. This research provides an efficient atom-economical approach to access a variety of highly substituted pyrrolidines in moderate to good yields. This protocol features readily available substrates, broad substrate scope, easy scale-up, high selectivities, and versatile transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhipeng Zheng, Youge Pu, Javier Adrio, Patrick J. Walsh
Summary: This study reports a synthetic method for trans-aziridines using imines and benzylic or alkyl halides with sulfenate anions (PhSO-) as catalysts. The method shows broad applicability and good diastereoselectivity, and can be used with substrates bearing heterocyclic aromatic groups, alkyl, and electron-rich and electron-poor aryl groups. Ring-opening reactions further allow functionalization of aziridines containing cyclopropyl or cyclobutyl groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Alla I. Vaskevych, Nataliia O. Savinchuk, Ruslan I. Vaskevych, Svitlana V. Shishkina, Mykhailo V. Vovk
Summary: 2-butenylquinazolin-4(3H)-ones can undergo intramolecular aza-Wacker cyclization to form methylene-substituted pyrrolo(pyrido)[2,1-b]quinazolinones when treated with the catalytic system Pd(OAc)(2)/PPh3/Cs2CO3/benzoquinone in dioxane or Pd(PPh3)(2)Cl-2/t-BuONa/Cs2CO3/benzoquinone in toluene. The latter catalytic system also reacts with pentenyl(hexenyl)quinazolin-4(3H)-ones, but leads to the formation of vinyl-substituted pyrrolo(pyrido)[2,1-b]quinazolinones via competition between aminopalladation of C-H multiple bonds and allylic C(sp(3))-H bond activation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Giuseppe Mazzeo, Giovanna Longhi, Sergio Abbate, Martina Palomba, Luana Bagnoli, Francesca Marini, Claudio Santi, Jianlin Han, Vadim A. Soloshonok, Emilio Di Crescenzo, Renzo Ruzziconi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Luca Sancineto, Francesca Mangiavacchi, Caterina Tidei, Luana Bagnoli, Francesca Marini, Antimo Gioiello, Jacek Scianowski, Claudio Santi
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Francesca Mangiavacchi, Leonardo Mollari, Luana Bagnoli, Francesca Marini, Claudio Santi
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2018)
Article
Chemistry, Medicinal
Daniela Dolciami, Marco Gargaro, Bruno Cerra, Giulia Scalisi, Luana Bagnoli, Giuseppe Servillo, Maria Agnese Della Fazia, Paolo Puccetti, Francisco J. Quintana, Francesca Fallarino, Antonio Macchiarulo
Article
Chemistry, Organic
Martina Palomba, Francesco Trappetti, Luana Bagnoli, Claudio Santi, Francesca Marini
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Martina Palomba, Luca Sancineto, Francesca Marini, Claudio Santi, Luana Bagnoli
Review
Chemistry, Medicinal
Francesca Mangiavacchi, Italo Franco Coelho Dias, Irene Di Lorenzo, Pawel Grzes, Martina Palomba, Ornelio Rosati, Luana Bagnoli, Francesca Marini, Claudio Santi, Eder Joao Lenardao, Luca Sancineto
Review
Biochemistry & Molecular Biology
Paola S. Hellwig, Thiago J. Peglow, Filipe Penteado, Luana Bagnoli, Gelson Perin, Eder J. Lenardio
Article
Biochemistry & Molecular Biology
Francesca Mangiavacchi, Pawel Botwina, Elena Menichetti, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Sergio F. Fonseca, Laura Abenante, Diego Alves, Agnieszka Dabrowska, Anna Kula-Pacurar, David Ortega-Alarcon, Ana Jimenez-Alesanco, Laura Ceballos-Laita, Sonia Vega, Bruno Rizzuti, Olga Abian, Eder J. Lenardao, Adrian Velazquez-Campoy, Krzysztof Pyrc, Luca Sancineto, Claudio Santi
Summary: Development of new antiviral drugs targeting SARS-CoV-2 is important in combating the COVID-19 pandemic, with selenium-functionalized quercetin derivatives showing promising inhibitory effects. In particular, 8-(p-tolylselenyl)quercetin has demonstrated significant antiviral activity at non-toxic concentrations. This study proposes a non-covalent mechanism for M-pro inhibition involving a hydrogen bond between the selenium atom and a specific residue in the catalytic pocket, explaining the compounds' efficacy.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Biochemistry & Molecular Biology
Pawel A. Grzes, Bonifacio Monti, Natalia Wawrusiewicz-Kurylonek, Luana Bagnoli, Luca Sancineto, Izabella Jastrzebska, Claudio Santi
Summary: The study describes a chemoselective and stereoselective Michael-type addition reaction in a biphasic system to synthesize novel steroidal selenides and sulfides, demonstrating an eco-friendly one-step process that allows for the preparation of variously decorated steroids starting from 1,4-androstadiene skeletons. This methodology could potentially lead to the development of new pharmaceutically active compounds with anticancer and antimicrobial properties.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Biochemistry & Molecular Biology
Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Luca Sancineto, Claudio Santi
Summary: This review discusses the FDA-approved drugs in 2021 that contain at least one halogen atom. The synthesis and therapeutic uses of these drugs are presented, highlighting the growing importance of halogens, particularly fluorine and chlorine, in the development of drugs for various diseases.
Review
Biochemistry & Molecular Biology
Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Luca Sancineto, Claudio Santi
Summary: This review discusses the top-selling small molecule orphan drugs based on their sales projections for 2026. Orphan drugs are designed to treat, prevent, or diagnose rare diseases or conditions. Most of these molecules target rare forms of cancer, with respiratory and central nervous systems being other commonly treated subcategories. The study highlights the significant growth of the orphan drugs market and its expected contribution to prescriptions by 2026.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Pharmacology & Pharmacy
Davide Benedetto Tiz, Luana Bagnoli, Ornelio Rosati, Francesca Marini, Claudio Santi, Luca Sancineto
Summary: This review describes recently FDA-approved drugs, many of which contain active moieties that have not been previously approved by the FDA. These drugs provide important new therapies for patients with multiple unmet diseases.
Article
Chemistry, Organic
Cristina Tomassini, Francesca Di Sarra, Bonifacio Monti, Luca Sancineto, Luana Bagnoli, Francesca Marini, Claudio Santi
Article
Chemistry, Organic
Martina Palomba, Emanuela De Monte, Andrea Mambrini, Luana Bagnoli, Claudio Santi, Francesca Marini
Summary: A novel three-component synthesis method for spirooxindole-tetrahydropyrrolizines has been developed, providing good yields and high diastereoselectivity. The method also shows good regioselectivities with aryl substituted vinyl selenones, offering a direct approach to biologically relevant compounds under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
