Article
Chemistry, Organic
Guanghui Wang, Yongqiang Wang, Zengzeng Li, Haotian Li, Mingwu Yu, Maofu Pang, Ximei Zhao
Summary: The gold-catalyzed cyclization/hydroboration of 1,6-enynes provides a facile and versatile method to access bicyclo[3.1.0]hexane boranes. The stable products can undergo various transformations.
Article
Chemistry, Organic
Xia Chen, Zengwei Luo, Yong Chen, Yonghui Zhang
Summary: A simple and efficient catalytic reaction for the synthesis of valuable functionalized compounds has been developed. The reaction proceeds in one step under environmentally friendly conditions and has shown excellent yields. The study also revealed the involvement of an unconventional intermediate in the reaction mechanism.
Article
Biochemistry & Molecular Biology
Stanislav Shmakov, Diana K. Latypova, Tatiana Shmakova, Artem A. Rubinshtein, Mark Chukin, Sergei G. Zhuravskii, Nickolay A. Knyazev, Alexander Stepakov, Michael M. Galagudza, Vitali M. Boitsov
Summary: A series of heterocyclic compounds containing spirofused barbiturate and 3-azabicyclo[3.1.0]hexane frameworks were studied as potential antitumor agents. The screened compounds showed significant antiproliferative activity against various cell lines and induced apoptosis in HeLa and CT26 cells. Confocal microscopy revealed changes in actin filaments and filopodium-like membrane protrusions in treated cells.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Review
Chemistry, Multidisciplinary
Yufeng Li, Jiajun Feng, Fei Huang, Jonathan B. Baell
Summary: 3-Azabicyclo[3.1.0]hexanes are important nitrogen-containing heterocycles found in biologically active natural products, drugs, and agrochemicals. The synthesis of these derivatives has made significant progress in recent decades, with various catalytic systems being developed. This review provides an overview of the efficient methods for synthesizing 3-azabicyclo[3.1.0]hexane derivatives since 2010, highlighting substrate scope, synthesis applications, and reaction mechanisms.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Guanghui Wang, Haotian Li, Yongqiang Wang, Zengzeng Li, Gang Liu, Ximei Zhao
Summary: A gold-catalyzed Si-H bond insertion reaction of 1,6-enynes with hydrosilanes via cyclopropyl gold carbene intermediates is reported, allowing facile and practical synthesis of bicyclo[3.1.0]hexane silanes. Furthermore, a gold-catalyzed carbene insertion into Ge-H bonds is reported for the first time.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Guanghui Wang, Haotian Li, Yongqiang Wang, Zengzeng Li, Gang Liu, Ximei Zhao
Summary: The gold-catalyzed Si-H bond insertion reaction of 1,6-enynes with hydrosilanes allows the practical and atom-economical synthesis of bicyclo[3.1.0]hexane silanes in moderate to excellent yields. Additionally, the gold-catalyzed carbene insertion into Ge-H bonds is reported for the first time.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Shuanggang Ma, Rubing Wang, Rongmei Gao, Xiaojing Wang, Yunbao Liu, Yong Li, Li Li, Yuhuan Li, Jing Qu, Shishan Yu
Summary: Two unprecedented polycyclic spirooliganones C and D with a novel carbon skeleton were isolated from the roots of Illicium oligandrum. Their structures and absolute configurations were determined, and a possible biosynthetic pathway was proposed. These compounds exhibited significant antiviral activity, showing potential as antiviral agents.
CHINESE CHEMICAL LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Jan Phillip Lemmerhirt, Andreas Isaak, Rongfang Liu, Max Kock, Constantin G. Daniliuc, Kenneth A. Jacobson, Laura H. Heitman, Anna Junker
Summary: A series of nucleosides based on bicyclo[3.1.0]hexane were synthesized and evaluated for their affinities to receptors. The most potent derivative 30 showed moderate A(3)AR affinity and high A(3)R selectivity. Some compounds tested in functional assays showed no off-target activity.
Article
Chemistry, Organic
Keisuke Mitsui, Maria E. K. Lie, Naoki Saito, Koichi Fujiwara, Mizuki Watanabe, Petrine Wellendorph, Satoshi Shuto
Summary: Novel gamma-aminobutyric acid (GABA) analogues with different backbones were designed based on the analysis of the bioactive form of a previous inhibitor. These compounds were synthesized using ring-closing metathesis and compound 4 showed selective low micromolar potency.
Article
Chemistry, Multidisciplinary
Zhen-Hong Yang, Peng Chen, Zhi-Chao Chen, Zhi Chen, Wei Du, Ying-Chun Chen
Summary: The chemoselective activation of Tsuji's 2-(cyanomethyl)allyl carbonates to generate palladium-trimethylenemethane 1,3-dipoles can be realized in the presence of Morita-Baylis-Hillman carbonates from activated ketones. The subsequent cascade annulations lead to the formation of complex frameworks with good to excellent enantioselectivity, while a similar annulation sequence using benzoyl aldehyde-derived substrates produces fused cyclopenta[b]furan architectures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Mengwu Xiao, Lvjie Xu, Ding Lin, Wenwen Lian, Manying Cui, Meng Zhang, Xiaowei Yan, Shuishi Li, Jun Zhao, Jiao Ye, Ailin Liu, Aixi Hu
Summary: A series of 4-thiazolinone derivatives were synthesized and evaluated for their inhibitory activities on neuraminidase from various influenza virus subtypes. The study identified several compounds with potent inhibitory activities against different influenza viral subtypes, indicating their potential as candidates for new anti-influenza drug development.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Pharmacology & Pharmacy
Sook Kwan Brown, Yeu-Yang Tseng, Ammar Aziz, Mariana Baz, Ian G. Barr
Summary: This study tested 3425 influenza B viruses collected from the Asia-Pacific region against four registered neuraminidase inhibitors (NAIs). It identified 45 influenza B viruses with reduced susceptibility to one or more NAIs, including some with newly identified neuraminidase mutations. The study highlights the potential impact of these mutations on the clinical effectiveness of NAIs in treating influenza B infections in humans.
ANTIVIRAL RESEARCH
(2022)
Article
Immunology
Konstantin Andreev, Jeremy C. Jones, Patrick Seiler, Ahmed Kandeil, Jasmine C. M. Turner, Subrata Barman, Adam M. Rubrum, Richard J. Webby, Elena A. Govorkova
Summary: The antiviral susceptibility of currently circulating highly pathogenic avian influenza A(H5N1) viruses was assessed using genotypic and phenotypic approaches. The majority of the viruses retain susceptibility to antiviral drugs, but novel mutations have been identified that reduce the inhibitory effects of certain drugs.
JOURNAL OF INFECTIOUS DISEASES
(2023)
Article
Chemistry, Multidisciplinary
Andreas J. Weidkamp, Martin Oestreich
Summary: This study reports on the development and application of a transfer hydrochlorination reagent based on a trichlorinated bicyclo[3.1.0]hexane core, which transfers two molecules of HCl per molecule of surrogate to a pi-basic substrate under B(C6F5)(3) catalysis. The Lewis acid-assisted chloride abstraction followed by thermal electrocyclic cyclopropyl-to-allyl cation ring opening releases ring strain as a previously unexploited driving force.
CHEMICAL COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Jiwei Zhang, Chuanfeng Liu, Ruifang Jia, Xujie Zhang, Jian Zhang, Chiara Bertagnin, Anna Bonomini, Laura Guizzo, Yuanmin Jiang, Huinan Jia, Shuzhen Jia, Xiuli Ma, Arianna Loregian, Bing Huang, Peng Zhan, Xinyong Liu
Summary: Introducing structurally diverse benzyl side chains at the C5-NH2 position of oseltamivir improves its binding affinity with neuraminidase and anti-influenza activity. We designed and synthesized novel oseltamivir derivatives with different N-heterocycle substituents that induce opening of the 150-loop of group-2 neuraminidases. Compound 6k showed broad-spectrum activity against wild-type neuraminidases and enhanced activity against H3N2 compared to oseltamivir carboxylate and zanamivir.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Medicinal
Alice Tamburrini, Cinzia Colombo, Anna Bernardi
MEDICINAL RESEARCH REVIEWS
(2020)
Article
Biochemistry & Molecular Biology
Rafael Bermeo, Anna Bernardi, Annabelle Varrot
Review
Chemistry, Organic
Anna Bernardi, Sara Sattin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Julie Pham, Alvaro Hernandez, Anna Cioce, Silvia Achilli, Giulio Goti, Corinne Vives, Michel Thepaut, Anna Bernardi, Franck Fieschi, Niels-Christian Reichardt
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Kanhaya Lal, Rafael Bermeo, Jonathan Cramer, Francesca Vasile, Beat Ernst, Anne Imberty, Anna Bernardi, Annabelle Varrot, Laura Belvisi
Summary: Burkholderia cenocepacia is a highly resistant Gram-negative bacterium that expresses the bacterial lectin BC2L-C, which may be a potential drug target. By solving the structure of BC2L-C and screening for active fragments, this research offers the opportunity to develop high affinity anti-adhesive glycomimetics for therapeutic use against Burkholderia cenocepacia.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Microbiology
Michel Thepaut, Joanna Luczkowiak, Corinne Vives, Nuria Labiod, Isabelle Bally, Fatima Lasala, Yasmina Grimoire, Daphna Fenel, Sara Sattin, Nicole Thielens, Guy Schoehn, Anna Bernardi, Rafael Delgado, Franck Fieschi
Summary: The study reveals that C-type lectin receptors (CLRS) can bind to the spike envelope protein of SARS-CoV-2, and DC-SIGN and L-SIGN among them can promote virus trans-infection. This discovery identifies a new mechanism for enhancing viral spread.
Article
Chemistry, Organic
Giulio Goti, Cinzia Colombo, Silvia Achilli, Corinne Vives, Michel Thepaut, Joanna Luczkowiak, Nuria Labiod, Rafael Delgado, Franck Fieschi, Anna Bernardi
Summary: By synthesizing cross-shaped glycodendrimers, simultaneous coordination of all four carbohydrate binding sites of the C-type lectin receptor DC-SIGN has been achieved. The tetravalent platform described here has potential applications in infectious diseases.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Nives Hribernik, Fabrizio Chiodo, Roland J. Pieters, Anna Bernardi
Summary: Recruiting natural antibodies to eliminate tumor cells is a highly specific and effective therapeutic strategy. This study reports the first rhamnose-based glycomimetic used for this purpose, which captures anti-rhamnose antibodies.
TETRAHEDRON LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Rafael Bermeo, Kanhaya Lal, Davide Ruggeri, Daniele Lanaro, Sarah Mazzotta, Francesca Vasile, Anne Imberty, Laura Belvisi, Annabelle Varrot, Anna Bernardi
Summary: This study aims to design and synthesize bifunctional C- or N-fucosides as glycomimetic antagonists to inhibit the interaction between BC2L-C-Nt and fucosylated human oligosaccharides. A modular route starting from key fucoside intermediates was implemented for the synthesis, and the new compounds were evaluated as BC2L-C-Nt ligands using various techniques. The study resulted in a hit molecule with significantly improved potency and two crystal structures of antagonist/lectin complexes.
ACS CHEMICAL BIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Sarah Mazzotta, Giulia Antonini, Francesca Vasile, Emilie Gillon, Jon Lundstrom, Annabelle Varrot, Laura Belvisi, Anna Bernardi
Summary: The inhibition of carbohydrate-lectin interactions is being explored for anti-adhesion therapy and biofilm destabilization against resistant pathogens. BC2L-C, a new type of lectin, can bind fucosides and mannosides, allowing it to crosslink host cells and bacterial cells. A study focused on developing glycomimetic antagonists of BC2L-C, with soluble ligands designed to interact with its fucose-specific N-terminal domain. The researchers identified a hit compound with improved water solubility and affinity for BC2L-C-Nt, which was further analyzed through biophysical techniques and X-ray crystallography.
Article
Chemistry, Multidisciplinary
Vanessa Porkolab, Martin Lepsik, Stefania Ordanini, Alexander St John, Aline Le Roy, Michel Thepaut, Emanuele Paci, Christine Ebel, Anna Bernardi, Franck Fieschi
Summary: DC-SIGN functions as the coreceptor for SARSCoV-2 virus, and a glycomimetic ligand called Polyman26 inhibits DC-SIGN-dependent trans-infection. By designing dendrimer constructs that can engage two binding sites of the tetrameric DC-SIGN simultaneously, the researchers were able to achieve nanomolar affinity. This study opens up possibilities for developing new virus attachment blockers for different C-type lectin receptors.
ACS CENTRAL SCIENCE
(2023)
Review
Biochemistry & Molecular Biology
Sarah Mazzotta, Vincenzo Rositano, Luca Senaldi, Anna Bernardi, Pietro Allegrini, Giovanni Appendino
Summary: This article provides a critical review of the mechanistic studies on scalemic natural products with multiple contiguous stereogenic centers up to the end of 2022. It identifies the mechanisms, such as the expression of antipodal enzymes/directing proteins or the erosion of optical purity by enzymatic or spontaneous reactions, that result in low optical purity. The article also discusses the analytical exploitations of scalemicity in natural products.
NATURAL PRODUCT REPORTS
(2023)
Article
Chemistry, Multidisciplinary
Sara Pollastri, Clara Delaunay, Michel Thepaut, Franck Fieschi, Anna Bernardi
Summary: In this study, it was found that the C-type lectin receptors DC-SIGN and L-SIGN bind to the SARS-CoV-2 spike glycoprotein and enhance viral trans-infection. A new compound was discovered as an inhibitor of their interaction with the spike glycoprotein, showing greater potency than mannose.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Nives Hribernik, Alice Tamburrini, Ermelinda Falletta, Anna Bernardi
Summary: A one-pot aziridine opening reaction using glycosyl thiols generated from anomeric thio-acetates produces thio-glycosides with a pseudo-disaccharide structure and N-linked tether. The reaction scope was explored on various mono- and disaccharides, leading to the synthesis of pseudo-glycosidic compounds. Unexpected anomerization of glycosyl thiols was observed, and factors affecting isomerization were investigated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Vanessa Porkolab, Carlo Pifferi, Ieva Sutkeviciute, Stefania Ordanini, Marwa Taouai, Michel Thepaut, Corinne Vives, Mohammed Benazza, Anna Bernardi, Olivier Renaudet, Franck Fieschi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)