Review
Biochemistry & Molecular Biology
Bichu Cheng, Lili Song, Fener Chen
Summary: Huperzine alkaloids, particularly Huperzine A, have shown potent inhibitory activity against acetylcholine esterase. The synthesis of Huperzine A has led to significant progress in the field and has also contributed to the total synthesis of other Huperzine alkaloids. This review focuses on the synthetic organic chemistry of Huperzines, as well as briefly covering their biosynthesis and medicinal chemistry.
NATURAL PRODUCT REPORTS
(2023)
Review
Plant Sciences
Arun K. Ghosh, Jennifer L. Mishevich, Melissa S. Jurica
Summary: Spliceostatins and thailanstatins are natural products with intriguing structural features and significant biological importance, known for their potent cytotoxicity against human cancer cell lines. Their ability to inhibit spliceosomes, particularly through binding to SF3B component, has opened up possibilities for developing new therapies based on small-molecule splicing modulators. The total syntheses of these natural products have led to the development of useful synthetic strategies and potent derivatives.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Organic
Victoria Sinka, Daniel A. Cruz, Victor S. Martin, Juan I. Padron
Summary: The shortest enantioselective total syntheses of (+)-isolaurepinnacin and (+)-neoisoprelaurefucin were achieved using a common parallel synthetic strategy based on Prins-Peterson cyclization in their core construction. In only one step, a seven-membered ring oxacycle with the correct cis-stereochemistry ring closure and the Δ4 position of the endocyclic double bond in (+)-isolaurepinnacin was obtained. This unsaturation was also necessary to access the bromodioxabicycle in (+)-neoisoprelaurefucin.
Article
Chemistry, Organic
Lei Zeng, Qian Lei, Weidong Rao, Lizhu Gao
Summary: A catalytic diastereoselective hetero-Diels-Alder reaction was developed for the synthesis of 3,4-dihydropyrans from alpha-haloacroleins and less polarized alkenes. Mechanistic studies revealed that 3,4-dihydropyran was produced through the ring expansion of cyclobutane, which was generated from the ring contraction of an initially formed unstable conformer.
Article
Chemistry, Organic
Zheye Zhang, Jiaining Liu, Shang Gao, Bo Su, Ming Chen
Summary: We describe the stereoselective syntheses of (E)- and (Z)-crotylboronates with alpha,alpha-disubstitution. The alkylation reaction exclusively occurs at the alpha position to the boryl groups in the starting crotylboronates, resulting in the desired boronates while maintaining the original alkene geometries. The resulting alpha,alpha-disubstituted crotylboronates can undergo aldehyde addition to afford allylated products with high stereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jinghui Hu, Qiang Du, Yao Zhao, Fei Zhang, Rizhi Chen, Jianrong Steve Zhou, Xiaojin Wu
Summary: A nickel-catalyzed intermolecular arylcyanation reaction of 8-aminoquinolinyl beta,gamma-unsaturated amides is reported. Diverse beta-cyano gamma-aryl amides with exclusive chemo- and regioselectivity were directly obtained through a three-component reaction. The practicality of this approach was further demonstrated through multigram scale reactions, expanded transformations of the nitrile product, late-stage modification of complex molecules, and direct drug synthesis.
Article
Chemistry, Multidisciplinary
Yanyu Chen, Zhaobo Wang, Wutong Zhao, Shitao Sun, Lu Yang, Junpeng Zhang, Di Zhang, Maosheng Cheng, Bin Lin, Yongxiang Liu
Summary: This paper reports a chelation-controlled cycloisomerization reaction of tryptamine-ynamide catalyzed by Ag(i)/PPh3, which allows access to the spiro[indole-3,4'-piperidine] scaffold in a racemic and diastereoselective manner. Diastereoselective products are achieved through a chiron approach. Density functional theory calculations show that strong non-covalent interactions between the substrate and catalyst/ligand complex stabilize the formation of the spiroindoleninium intermediate via cation-pi-pi interactions.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jiaming Liu, Shang Gao, Ming Chen
Summary: Highly stereo- and enantioselective synthesis of (E)-delta-hydroxymethyl-anti-homoallylic alcohols is achieved through reactions between aldehydes and chiral nonracemic alpha-borylmethyl-(E)-crotylboronate, resulting in high E-selectivities and enantioselectivities.
Article
Chemistry, Multidisciplinary
Kanak Kanti Das, Samir Manna, Santanu Panda
Summary: Asymmetric multicomponent reactions allow the stitching of multiple functional groups in an enantioselective and atom economical manner. The use of boron-based reagents in such reactions offers advantages such as non-toxicity, high stability, and easy conversion to other functional groups in a stereoselective manner. In the past decade, several transition metal catalyzed asymmetric multicomponent strategies using boron-based reagents have been developed.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hua Wang, Shun Wang, Vincent George, Galder Llorente, Burkhard Koenig
Summary: We have developed a photo-induced reaction that allows the in situ generation of highly reactive alkyl diazo species from carbonyl precursors. These diazo intermediates can undergo efficient C-H insertion with aldehydes, resulting in the synthesis of aldehydes and ketones. This method can be used for the iterative synthesis of densely functionalized carbonyl compounds by sequentially trapping the diazo species with different aldehydes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Peng Duan, He Zhao, Jian Yang, Liang Cao, Huanfeng Jiang, Min Zhang
Summary: This study demonstrates an efficient synthetic method for the construction of novel fluorinated γ-amino acid esters by difunctionalization of cyclic ethers at the alpha- and beta-sites. The transformation of a range of cyclic ethers with various amines and ethyl trifluoropyruvate under mild conditions allows for the practical enrichment of the library of fluorinated amino acid derivatives from cost-effective and readily available starting materials.
Article
Chemistry, Multidisciplinary
Anton Dmitrienko, Melanie Pilkington, Georgii I. Nikonov
Summary: The Al-I compound NacNacAl serves as a template for chemoselective coupling reactions between carbonyls and pyridine, with different carbonyl substrates leading to different reaction pathways and products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Mohammed Salim Mohammed, Homa Targhan, Kiumars Bahrami
Summary: A novel pseudo-homogeneous catalyst was designed and synthesized in this study. Amine-functionalized graphene oxide quantum dots (N-GOQDs) were prepared from graphene oxide (GO) through a simple oxidation fragmentation process. These N-GOQDs were then modified with quaternary ammonium hydroxide groups. The efficient catalytic performance of the synthesized N-GOQDs/OH- in the epoxidation reaction of alpha,beta-unsaturated ketones using aqueous H2O2 as the oxidant at room temperature was demonstrated. The procedure showed advantages such as the utilization of a green oxidant, high yields of the epoxide products, utilization of non-toxic reagents, and reusability of the catalyst without significant loss of activity.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Organic
Congcong Yin, Yingmin Pan, Xumu Zhang, Qin Yin
Summary: An unprecedented Rh-catalyzed asymmetric and diastereoselective hydrogenation method for easily accessible α,β-disubstituted unsaturated lactams was reported. This method provides synthetically valuable chiral lactams with 1,2-consecutive stereocenters. The reaction can be performed on a gram scale and the products can be transformed into enantiomerically pure trans-3,4-disubstituted piperidines, which are prevalent structural units in medicinal agents.
Article
Chemistry, Organic
Chenghao Li, Wei-Fang Zuo, Jin Zhou, Wu-Jingyun Zhou, Meng Wang, Xiang Li, Gu Zhan, Wei Huang
Summary: In this study, axially chiral 3,4'-indole-pyrazole derivatives were successfully synthesized through the chiral phosphoric acid-catalyzed Mannich reaction. High diastereoselectivities and enantioselectivities could be obtained in most cases. The presence of a 5-pyrazolyl acetate moiety in the substrate proved crucial for improving the reactivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Teresa Basile, Luca Capaldo, Davide Ravelli, Paolo Quadrelli
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Mattia Moiola, Marco Leusciatti, Paolo Quadrelli
Article
Chemistry, Organic
Marco Corti, Marco Leusciatti, Mattia Moiola, Mariella Mella, Paolo Quadrelli
Summary: By mild oxidation of nitrile oxides with tertiary amine N-oxides, two new nitrosocarbonyl intermediates with carbohydrate-based chiral substituents were successfully synthesized and trapped, leading to hetero Diels-Alder cycloadducts and ene adducts from fair to excellent yields. The methodology shows promise in widening access to nitrosocarbonyls, versatile tools in organic synthesis, through easy conversion of aldoximes into hydroxymoyl halides.
SYNTHESIS-STUTTGART
(2021)
Article
Biochemistry & Molecular Biology
Alice Triveri, Carlos Sanchez-Martin, Luca Torielli, Stefano A. Serapian, Filippo Marchetti, Giovanni D'Acerno, Valentina Pirota, Matteo Castelli, Elisabetta Moroni, Mariarosaria Ferraro, Paolo Quadrelli, Andrea Rasola, Giorgio Colombo
Summary: In this study, the allosteric inhibition of the mitochondrial chaperone TRAP1 by a small molecule ligand is examined. The findings are used to design novel derivatives with interesting biological properties. The implications of this approach in understanding molecular regulation and designing allosteric small molecule modulators are discussed.
JOURNAL OF MOLECULAR BIOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Marco Corti, Rossella Chiara, Lidia Romani, Barbara Mannucci, Lorenzo Malavasi, Paolo Quadrelli
Summary: Lead halide perovskite nanocrystals were utilized as photocatalysts in organic reactions, showing applicability to various olefinic substrates and leading to desymmetrized hydroxy-ketone derivatives and unsaturated ketones as products.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Polymer Science
Lisa Rita Magnaghi, Camilla Zanoni, Denise Bellotti, Giancarla Alberti, Paolo Quadrelli, Raffaela Biesuz
Summary: Carboxymethyl cellulose is a promising cellulose derivative with low cost, abundancy, biocompatibility, unique properties, and chemical reactivity. This study proposes a two-step reaction for covalent anchoring of sulfonic groups to CMC, allowing for the production of ready-to-use functional materials with high yields. By utilizing a pH-sensitive dye as a sulfonated molecule, the functional material shows potential for development of colorimetric miniaturized sensors, as demonstrated in an application on real samples.
Article
Chemistry, Analytical
Lisa Rita Magnaghi, Giancarla Alberti, Camilla Zanoni, Marta Guembe-Garcia, Paolo Quadrelli, Raffaela Biesuz
Summary: A novel 3 x 4 colorimetric sensing platform, named chemometric-assisted litmus test (CLT), has been developed using commercial pH indicators anchored to ethylene vinyl alcohol (EVOH). The CLT can accurately determine pH within a wide range (pH 1-13) and specific narrow ranges, with errors below 0.5 pH units. The experimental procedure is simple, quick and reliable, with equilibration reached in less than 2 hours, CLT pictures acquired by a camera, and data treatment performed using chemometric techniques such as principal component analysis (PCA) and partial least square regression (PLS) for RGB indices.
Article
Chemistry, Multidisciplinary
Marco Leusciatti, Beatrice Macchi, Francesca Marino-Merlo, Antonio Mastino, Giulia Morra, Paolo Quadrelli
Summary: Isoxazoline-carbocyclic monophosphate nucleotides with antiviral activity were designed and synthesized using chemical synthesis methods. Preliminary activity and toxicity tests were performed at the cellular level.
Article
Food Science & Technology
Lisa Rita Magnaghi, Camilla Zanoni, Giancarla Alberti, Paolo Quadrelli, Raffaela Biesuz
Summary: This study presents a dual-optode label device that can monitor the freshness of fish products in real-time. The device utilizes color changes to indicate the spoilage level of the fish products and has the ability of naked-eye readout and chemometric modeling. This device demonstrates good sensing performance and versatility, making it an interesting candidate for smart labels in packed fish products.
ACS FOOD SCIENCE & TECHNOLOGY
(2022)
Review
Chemistry, Inorganic & Nuclear
Marco Corti, Sara Bonomi, Rossella Chiara, Lidia Romani, Paolo Quadrelli, Lorenzo Malavasi
Summary: Metal halide perovskites (MHPs) show promise as photocatalysts in organic syntheses, offering advantages over traditional photocatalysts due to their optimal electronic properties. While still in the early stages, the rich structural and chemical tunability of MHPs will likely make them a central research topic in the future.
Article
Materials Science, Multidisciplinary
Rossella Chiara, Marta Morana, Massimo Boiocchi, Mauro Coduri, Marinella Striccoli, Francesco Fracassi, Andrea Listorti, Arup Mahata, Paolo Quadrelli, Mattia Gaboardi, Chiara Milanese, Luca Bindi, Filippo De Angelis, Lorenzo Malavasi
Summary: The elucidation of structure-property correlation in 2D metal halide perovskite is crucial for understanding optical properties dependence on structural distortions and designing novel tailored materials. Novel 2D germanium bromide perovskites demonstrate a dependence of band gap value and emission characteristics in terms of Stokes shift and peak width on octahedral distortion parameters, providing insights for future design of layered lead-free materials. Comparing with Sn- and Pb-based materials, intrinsic increased distortion induced by germanium is observed, particularly on octahedral bond elongation and bond angle variance.
JOURNAL OF MATERIALS CHEMISTRY C
(2021)
Article
Chemistry, Multidisciplinary
Marco Leusciatti, Barbara Mannucci, Teresa Recca, Paolo Quadrelli
Summary: The use of Cyclopenta[d]isoxazoline aminols in the synthesis of beta-turn mimics has been studied. The choice of peptide chains can affect the applicability and limitations of these scaffolds as beta-turn inducers. The proper design of peptide chains deeply influences the potential use of nitrosocarbonyl-based compounds as turn-inducers.
Article
Food Science & Technology
Lisa Rita Magnaghi, Federica Capone, Giancarla Alberti, Camilla Zanoni, Barbara Mannucci, Paolo Quadrelli, Raffaela Biesuz
Summary: This research focuses on developing an efficient sensing device for detecting milk freshness under typical home conditions. The study utilizes chemometric tools on optode array RGB triplets to visualize, compare, and predict the spoilage of commercial types of milk, representing a significant advancement in the field of freshness indicators for dairy products.
ACS FOOD SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Physical
Marco Corti, Rossella Chiara, Lidia Romani, Barbara Mannucci, Lorenzo Malavasi, Paolo Quadrelli
Summary: In this study, g-C3N4/metal halide perovskite composites were used for the first time as photocatalysts for in situ(1)O2 generation to perform hetero Diels-Alder, ene, and oxidation reactions. The method was applicable to various olefinic substrates, producing desymmetrized hydroxy-ketone derivatives, unsaturated ketones, and epoxides. While some limitations were observed, the experimental protocol serves as a platform for further exploring the applicability of MHPs in organic reactions.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Food Science & Technology
Lisa Rita Magnaghi, Giancarla Alberti, Chiara Milanese, Paolo Quadrelli, Raffaela Biesuz
Summary: The study introduces an innovative smart label for naked-eye evaluation of protein food freshness, utilizing polymeric sensing films with six miniaturized sensors. These sensors, obtained by binding six pH indicators to an ethylene vinyl alcohol copolymer, are characterized using various instrumental techniques and successfully applied for poultry meat and cod fillet spoilage monitoring.
ACS FOOD SCIENCE & TECHNOLOGY
(2021)