Review
Chemistry, Organic
Rodney A. A. Fernandes, Sanjita Moharana, Gulenur Nesha Khatun
Summary: This tutorial review highlights the recent efforts of researchers in the total synthesis of complex guaianolides. Various strategies and new methods, including catalytic reactions, have been employed to achieve these syntheses. The review also emphasizes the importance of enhancing diversity and sustainability in the synthesis of these natural products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Inorganic & Nuclear
Pragyandeepti Behera, Satyabrata Subudhi, Suraj Prakash Tripathy, Kulamani Parida
Summary: Metal organic frameworks (MOFs), fabricated through co-ordination interaction between metal nodes and organic linkers, have attracted significant interest as photo-catalytic materials due to their special features such as high surface area, tuneable porosity, and remarkable light absorption capacity. This review comprehensively discusses the design and fabrication of MOF derived nano-materials (MDNMs) with various morphological and physico-chemical characteristics. The photocatalytic applications of MDNMs and their superiority are also described, along with detailed mechanistic pathways.
COORDINATION CHEMISTRY REVIEWS
(2022)
Review
Chemistry, Multidisciplinary
Xiaopeng Peng, Abdur Rahim, Weijie Peng, Feng Jiang, Zhenhua Gu, Shijun Wen
Summary: This article summarizes the recent advances in the research field of cyclic aryliodoniums, including their design and synthetic applications. The general preparation of typical diphenyl iodoniums, construction of heterocyclic iodoniums and monoaryl iodoniums are described. The use of cyclic aryliodoniums as initiators for cascade reactions and the construction of complex structures such as polycycles and biaryls are discussed. Furthermore, the recent advance of cyclic aryliodoniums as halogen-bonding organocatalysts is described.
Review
Chemistry, Multidisciplinary
Jiawei Sun, He Yang, Wenjun Tang
Summary: This tutorial review summarizes the total synthesis of complex dimeric natural products and discusses various dimerization strategies. By highlighting selected representative examples, it aims to demonstrate the recent tactics of dimerization and provide insights on structural and chemical properties of related natural products, promoting advancements in organic synthesis and biological studies.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Applied
Christina G. Connor, Jacob C. DeForest, Phil Dietrich, Nga M. Do, Kevin M. Doyle, Shane Eisenbeis, Elizabeth Greenberg, Sarah H. Griffin, Brian P. Jones, Kris N. Jones, Michael Karmilowicz, Rajesh Kumar, Chad A. Lewis, Emma L. McInturff, J. Christopher McWilliams, Ruchi Mehta, Bao D. Nguyen, Anil M. Rane, Brian Samas, Barbara J. Sitter, Howard W. Ward, Mark E. Webster
Summary: The development of a commercial route towards the JAK1 inhibitor abrocitinib involves a late-stage Lossen rearrangement to obtain the desired compound, which is then sulfonylated using a novel water-tolerable triazole sulfonylating reagent to provide the active pharmaceutical ingredient.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Chao Xu, Hao Zhang, Shouang Lan, Jinggong Liu, Shuang Yang, Qi Zhang, Xinqiang Fang
Summary: Transition-metal-catalysed reactions of cyclic ethynylethylene carbonates have been extensively investigated due to their robustness in forming new bonds and constructing diverse molecules. A novel reaction pattern is reported, where cyclic ethynylethylene carbonates firstly undergo rearrangement to release allenal intermediates, which then react with various nucleophiles to produce synthetically useful allylic and propargylic allenols, phosphorus ylides, and cyclopropylidene ketones through an addition process rather than substitution pathway. The products allow for further transformations, and mechanistic studies reveal that the reaction proceeds via base-mediated deprotonation as the key step to induce the rearrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Biochemistry & Molecular Biology
Hardeep Singh Tuli, Prangya Rath, Abhishek Chauhan, Anuj Ranjan, Seema Ramniwas, Katrin Sak, Diwakar Aggarwal, Manoj Kumar, Kuldeep Dhama, E. Hui Clarissa Lee, Kenneth Chun-Yong Yap, Sharah Mae Capinpin, Alan Prem Kumar
Summary: Cucurbitacins, a group of highly oxidized tetracyclic triterpenoids found in cucumbers, have potential medical uses. They interact with various cellular targets to inhibit cancer cell growth through induction of apoptosis, cell-cycle arrest, anti-metastasis, and anti-angiogenesis. They may also be used in combination with other drugs to overcome treatment resistance in cancer cells. This study focuses on finding molecular targets for cucurbitacins in suppressing malignant processes.
Article
Chemistry, Physical
Fei Cao, Wen-Tao Tao, Qian Yu, Chu-Xuan Xu, Jin-Tao Cheng, Ruo-Xi Liu, Qing-Wei Zhao, Xin-Hang Jiang, Yu Liu, Yong-Quan Li, Zha-Jun Zhan, Ting Shi, Xu-Ming Mao
Summary: This study identified two new semi-pinacolases from the epoxide hydrolase family, expanding the biocatalyst family for semipinacol rearrangement. Through comprehensive mutations and chemical calculations, critical residues were identified for the catalytic mechanisms of selective epoxide collapse and subsequent SPR.
Article
Chemistry, Multidisciplinary
Thiago A. Grigolo, Joel M. Smith
Summary: A practical protocol for the first regiodivergent asymmetric addition of aryl and alkenyl organometallic reagents to substituted N-alkyl pyridinium heterocycles is described. The couplings proceed with high regiochemical and stereochemical selectivities, and provide access to chiral 1,2,3- and 1,3,4-trisubstituted dihydropyridine products, controlled by judicious choice of nitrogen activating agent. To this end, a correlation was found between the parameterized size of the activating group and the C2/C4 regioselectivity in the couplings. The utility of the described chemistry was demonstrated in two concise asymmetric syntheses of (+)-N-methylaspidospermidine and (-)-paroxetine.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Sayan Kar, Yinjun Xie, Quan Quan Zhou, Yael Diskin-Posner, Yehoshoa Ben-David, David Milstein
Summary: A new method for amide bond synthesis under mild conditions using ruthenium PNNH complexes has been developed, avoiding the high reaction temperatures required by traditional methods and successfully synthesizing several commercially available pharmaceutical drugs.
Article
Biochemistry & Molecular Biology
Christina Mountaki, Ioannis Dafnis, Eirini A. Panagopoulou, Paraskevi B. Vasilakopoulou, Michalis Karvelas, Antonia Chiou, Vaios T. Karathanos, Angeliki Chroni
Summary: The study found that polar phenols can affect the AD-related pathogenic functions of apoE4 forms, with certain compounds preventing cellular changes by modulating redox status and improving the structure of apoE4 forms. This research provides evidence that natural compounds could modify the structure of apoE4 forms and ameliorate AD-related pathogenic effects.
FREE RADICAL BIOLOGY AND MEDICINE
(2021)
Article
Chemistry, Organic
Zachary Schwartz, Chelsea Valiton, Myles Lovasz, Andrew G. Roberts
Summary: Ammonium ylide based [2,3]-sigmatropic and [1,2]-Stevens rearrangements are used to convert tertiary amines into rearranged and functionalized intermediates for the synthesis of polycyclic natural products. This review summarizes recent applications of these rearrangement reactions in formal and total synthesis and discusses innovative improvements to these transformations.
SYNTHESIS-STUTTGART
(2023)
Review
Chemistry, Inorganic & Nuclear
Kazuhiko Matsumoto, Michael Gerken
Summary: Sulfur and fluorine play crucial roles in main group chemistry, with SF4 and its derivatives exhibiting versatile reactivities and functionalities. Recent advances in SF4-related chemistry have shown its potential in organic synthesis and industrial applications.
DALTON TRANSACTIONS
(2021)
Review
Biotechnology & Applied Microbiology
Tien V. Vu, Ngan Thi Nguyen, Jihae Kim, Jong Chan Hong, Jae-Yean Kim
Summary: Prime editing technology uses an extended guide RNA to direct a fusion peptide to a specific location in the genome, enabling precise gene editing. This groundbreaking tool has potential in improving crop varieties, but efficiency limitations exist in certain plants.
PLANT BIOTECHNOLOGY JOURNAL
(2024)
Article
Chemistry, Applied
Yahui Guo, Helena T. N. N. Amunyela, Yuliang Cheng, Yunfei Xie, Hang Yu, Weirong Yao, Hung-Wing Li, He Qian
Summary: Metal nanoclusters, especially protein-templated gold nanoclusters, have attracted significant interest for their unique properties and potential applications. Natural proteins serve as ideal templates for the synthesis of these nanoclusters, allowing for exploration of their properties and applications in various fields.
Article
Chemistry, Medicinal
Margherita Brindisi, A. Prasanth Saraswati, Simone Brogi, Sandra Gemma, Stefania Butini, Giuseppe Campiani
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Review
Chemistry, Medicinal
Tuhina Khan, Nicola Relitti, Margherita Brindisi, Stefania Magnano, Daniela Zisterer, Sandra Gemma, Stefania Butini, Giuseppe Campiani
MEDICINAL RESEARCH REVIEWS
(2020)
Article
Chemistry, Medicinal
Arun K. Ghosh, Margherita Brindisi
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Medicinal
A. Prasanth Saraswati, Nicola Relitti, Margherita Brindisi, Jeremy D. Osko, Giulia Chemi, Stefano Federico, Alessandro Grillo, Simone Brogi, Niamh H. McCabe, Richard C. Turkington, Ola Ibrahim, Jeffrey O'Sullivan, Stefania Lamponi, Magda Ghanim, Vincent P. Kelly, Daniela Zisterer, Rebecca Amet, Patricia Hannon Barroeta, Francesca Vanni, Cristina Ulivieri, Daniel Herp, Federica Sarno, Antonella Di Costanzo, Fulvio Saccoccia, Giovina Ruberti, Manfred Jung, Lucia Altucci, Sandra Gemma, Stefania Butini, David W. Christianson, Giuseppe Campiani
ACS MEDICINAL CHEMISTRY LETTERS
(2020)
Article
Chemistry, Medicinal
Nicola Relitti, A. Prasanth Saraswati, Giulia Chemi, Margherita Brindisi, Simone Brogi, Daniel Herp, Karin Schmidtkunz, Fulvio Saccoccia, Giovina Ruberti, Cristina Ulivieri, Francesca Vanni, Federica Sarno, Lucia Altucci, Stefania Lamponi, Manfred Jung, Sandra Gemma, Stefania Butini, Giuseppe Campiani
Summary: This study describes the synthesis of potent and selective quinolone-based histone deacetylase 6 (HDAC6) inhibitors, which showed good to excellent anticancer activity in cellular studies by inducing tumor cell death through modulation of protein deacetylation.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Giuseppe Campiani, Caterina Cavella, Jeremy D. Osko, Margherita Brindisi, Nicola Relitti, Simone Brogi, A. Prasanth Saraswati, Stefano Federico, Giulia Chemi, Samuele Maramai, Gabriele Carullo, Benedikt Jaeger, Alfonso Carleo, Rosaria Benedetti, Federica Sarno, Stefania Lamponi, Paola Rottoli, Elena Bargagli, Carlo Bertucci, Daniele Tedesco, Daniel Herp, Johanna Senger, Giovina Ruberti, Fulvio Saccoccia, Simona Saponara, Beatrice Gorelli, Massimo Valoti, Breandan Kennedy, Husvinee Sundaramurthi, Stefania Butini, Manfred Jung, Katy M. Roach, Lucia Altucci, Peter Bradding, David W. Christianson, Sandra Gemma, Antje Prasse
Summary: The text introduces the characteristics of Idiopathic Pulmonary Fibrosis and the study related to the abnormal HDAC activities, presenting a series of hHDAC6 inhibitors as potential pharmacological tools for IPF treatment. The optimization and efficacy of new molecules were investigated for their capability in reverting the IPF phenotype.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Antonella Ilenia Alfano, Elisabetta Buommino, Maria Grazia Ferraro, Carlo Irace, Angela Zampella, Heiko Lange, Margherita Brindisi
Summary: The study presents an efficient flow process for the rapid modulation of reagents for Joullie-Ugi multicomponent reactions using spiroindolenines. By combining interrupted Fischer reaction for spiroindolenine synthesis with Joullie-Ugi-type modification in a telescoped flow process, the overall yield of product formation is significantly increased in less than 2 hours compared to 48 hours in batch mode. The developed protocol serves as a general tool for the rapid and facile generation of peptidomimetic compounds, with preliminary biological assessments conducted for the prepared compounds.
Review
Chemistry, Multidisciplinary
Antonella lenia Alfano, Heiko Lange, Margherita Brindisi
Summary: The formation of amide bonds is essential in organic and synthetic medicinal chemistry. In recent years, the application of flow chemistry in amide bond formation has shown significant advantages and potential for development. This review summarizes and compares various methods and discusses future needs and prospects for sustainable synthesis.
Article
Chemistry, Medicinal
Simona Barone, Emilia Cassese, Antonella Ilenia Alfano, Margherita Brindisi, Vincenzo Summa
Summary: This article presents the latest evidence linking HDAC6 activity and expression with cystic fibrosis phenotype, as well as exploring the potential and future perspectives in the field of HDAC6 modulators in cystic fibrosis.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Antonella Ilenia Alfano, Sveva Pelliccia, Giacomo Rossino, Orazio Chianese, Vincenzo Summa, Simona Collina, Margherita Brindisi
Summary: The handling of hazardous, toxic, and pollutant chemicals and high-risk intermediates remains a challenge for the efficacy, safety, and scale-up of chemical rearrangements. However, continuous-flow technology has emerged as a powerful tool for driving these reactions, offering easy, controlled, and safer chemistry protocols with minimal side products and increased reaction yields. This Technology Note provides an overview of recent chemical rearrangements using continuous-flow approaches, focusing on Curtius, Hofmann, and Schmidt reactions, and showcases their advantages, safety aspects, and applications in generating privileged scaffolds and active pharmaceutical ingredients.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Medicinal
Antonella Ilenia Alfano, Sveva Pelliccia, Giacomo Rossino, Orazio Chianese, Vincenzo Summa, Simona Collina, Margherita Brindisi
Summary: In recent years, photochemistry has become increasingly important in academia and the pharmaceutical industry. Continuous-flow chemistry has helped overcome the issues of long photolysis times and light penetration reduction, making photochemical rearrangements more controlled and efficient. This article highlights the benefits of flow chemistry in photochemical rearrangements and showcases recent advances in the synthesis of pharmaceutically relevant substructures using photo-rearrangements in continuous flow.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Antonella Ilenia Alfano, Andrea Sorato, Alessia Ciogli, Heiko Lange, Margherita Brindisi
Summary: Catalytic enantioselective Strecker reactions on achiral substrates are an effective strategy for synthesizing α-amino nitriles. We developed a flow-based methodology for enantioselective Strecker reactions using ethyl cyanoformate as a safe cyanide source, a cinchona-based catalyst, and methanol as an additive. Through extensive parameter exploration, we identified the most efficient reagent mixing mode, optimal solvent, minimum catalyst loading, additive, temperature, and residence time. This method enables fast and complete formation of α-amino nitrile products, reducing yield drop due to indolenine degradation in batch reactions. We also propose a simple procedure for catalyst recycling, suggesting potential sustainability and further optimization of this methodology.
JOURNAL OF FLOW CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Andrea Porcheddu, Rita Mocci, Margherita Brindisi, Federico Cuccu, Claudia Fattuoni, Francesco Delogu, Evelina Colacino, Maria Valeria D'Auria
Summary: An environmentally friendly mechanochemical protocol was developed to synthesize indoles and indolines using oxalic acid and dimethylurea. The solvent-free procedure showed versatility and wide scope, leading to variously decorated compounds. The methodology also has potential for preparing compounds of pharmaceutical interest.
Review
Chemistry, Multidisciplinary
Antonella Ilenia Alfano, Margherita Brindisi, Heiko Lange
Summary: The use of flow chemistry allows for more efficient generation of privileged scaffolds, implementation of multistep transformations, and development of green and sustainable processes in pharmaceutical chemistry. This review discusses the application of flow chemistry in the synthesis of privileged scaffolds and provides authors' perspectives on potential future directions in the field.
Article
Chemistry, Multidisciplinary
Antonella Ilenia Alfano, Angela Zampella, Ettore Novellino, Margherita Brindisi, Heiko Lange
REACTION CHEMISTRY & ENGINEERING
(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)
