Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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, Multidisciplinary
Maximilian Scheruebl, Constantin G. Daniliuc, Armido Studer
Summary: The article introduces the application of arynes as radical acceptors, showing how the stable radical TEMPO can react with different ortho-substituted benzynes to generate aryl radicals for subsequent cyclizations, eventually being trapped by TEMPO. This method provides a novel approach for the convenient synthesis of various dihydrobenzofurans, oxindoles, and sultones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xianqing Wu, Baixue Luan, Wenyu Zhao, Feng He, Xin-Yan Wu, Jingping Qu, Yifeng Chen
Summary: This study presents a nickel-catalyzed reductive cross-coupling reaction for the desymmetric dicarbofunctionalization of 1,6-dienes. By leveraging an underdeveloped chiral ligand, the reaction selectively forms pyrrolidinones bearing two nonadjacent stereogenic centers, enabling rapid synthesis of complex chiral fused-heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shu-Jie Chen, Zhi-Qing He, Guo-Shu Chen, Cheng Zhao, Chang-Ping Chen, Yin-Yin Zhuang, Long Chen, Yun-Lin Liu
Summary: A new class of Michael acceptors, tetrazolyl-trifluor-omethyl alkenes, has been discovered. They undergo Michael-type addition with aliphatic amines and azoles to produce beta-trifluoromethyl alkylamines and CF3- substituted 1,2-bisazole derivatives, respectively. Some of the products can also undergo microwave-assisted intramolecular denitrogenative annulation, leading to the formation of CF3-substituted 1,4,5,6-tetrahydro-1,2,4-triazines.
Article
Chemistry, Physical
Bo-Han Zhu, Ying-Qi Zhang, Hao-Jin Xu, Long Li, Guo-Cheng Deng, Peng-Cheng Qian, Chao Deng, Long-Wu Ye
Summary: An efficient copper-catalyzed tandem alkyne hydration/intramolecular Mannich reaction has been investigated for the synthesis of valuable compounds. This method allows the efficient synthesis of 3,4-dihydro-2-quinolones with high regio-, diastereo-, and enantioselectivity.
Article
Biochemistry & Molecular Biology
Caleigh S. Garton, Noelle K. DeRose, Dylan Dominguez, Maria L. Turbi-Henderson, Ashley L. Lehr, Ashley D. Padilla, Scott D. Twining, Stephanie Casas, Chidozie O. Alozie, Azad L. Gucwa, Mohammed R. Elshaer, Michael De Castro
Summary: A series of 2-deoxy-2-iodo-alpha-d-mannopyranosylbenzotriazoles were successfully synthesized using the benzyl, 4,6-benzylidene and acetyl protected D-glucal in the presence of N-iodosuccinimide. The method was extended to the preparation of substituted 2-deoxy-beta-d-glucopyranosylimidazoles. The anticancer properties of the compounds were evaluated in viability studies with promising results, with N-[3,4,6-tri-O-benzyl-2-deoxy-alpha-d-glucopyranosyl]-1H-benzotriazole and N-[3,4,6-tri-O-acetyl-2-deoxy-alpha-d-glucopyranosyl]-2H-benzotriazole showing potent cancer cell inhibition.
Article
Chemistry, Multidisciplinary
Raffaella Mancuso, Alex De Salvo, Patrizio Russo, Aurelia Falcicchio, Nicola Della Ca, Leonardo Pantoja Munoz, Bartolo Gabriele
Summary: The PdI2/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols selectively produces dihydrofuroquinolinone derivatives in fair to high yields (60%-89%) and excellent turnover numbers (180-267 mol of product per mol of Pd) over 19 examples. This reaction involves the catalytic construction of two rings and three new bonds in one step, providing high value added fused heterocyclic structures from readily available materials.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Svetlana Martynovskaya, Arsalan B. Budaev, Igor A. Ushakov, Tatyana N. Borodina, Andrey Ivanov
Summary: This article demonstrates the synthesis of two important fused heterocyclic compounds by controlling only one reaction parameter and using only two available building blocks. The synthesis is influenced by the water content of the medium.
Article
Biochemistry & Molecular Biology
Loana I. Monzon, Nicole C. M. Rocha, Gabriela T. Quadros, Pamela P. P. Nunes, Roberta Cargnelutti, Raquel G. Jacob, Eder J. Lenardao, Gelson Perin, Daniela Hartwig
Summary: A general methodology for synthesizing valuable 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines was developed by reacting 2-azidobenzaldehyde with phenylchalcogenylacetonitriles using potassium carbonate as a catalyst. The method tolerated a variety of functional groups and yielded twelve different 4-(phenylchalcogenyl)tetrazolo[1,5-a]quinolines selectively. The structure of the synthesized 4-(phenylselenyl)tetrazolo[1,5-a]quinoline was confirmed by X-ray analysis.
Article
Biochemistry & Molecular Biology
Laura F. Pena, Enol Lopez, Angel Sanchez-Gonzalez, Asuncion Barbero
Summary: A convenient method has been developed for the regioselective synthesis of allyl- and vinylsilyl alcohols from a common precursor by selecting suitable reaction conditions. These alcohols have been used in silyl-Prins cyclizations to prepare disubstituted oxygenated heterocycles in a one-pot sequential reaction. The reaction outcomes are highly dependent on the starting alkenylsilyl alcohol and reaction conditions, with various competitive pathways observed. However, the use of vinylsilyl alcohols has shown promising results in the preparation of differentially substituted cis-2,6-dihydropyrans.
Article
Chemistry, Applied
Bartosz Bisek, Wojciech Chaladaj
Summary: This study describes the Pd-catalyzed tandem cyclization/coupling of internal β-propargylic β-ketoesters with (hetero)aryl bromides. Two protocols are established to selectively produce either 2-benzylidene-dihydrofurans or 2-benzyl-furans. The proposed catalytic cycle involves oxidative addition, substitution of bromide with alkyne, rate-limiting anti-selective 5-exo-dig oxocyclization, deprotonation of the oxonium intermediate, and reductive elimination.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Stephanie Lee, Tilo Sohnel, Jonathan Sperry
Summary: In this study, unexpected results emerged during the synthetic study of the unique triazocane present in hicksoane alkaloids. The mechanisms behind the formation of the reaction products were elucidated through control reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ramon Arora, Jose F. Rodriguez, Andrew Whyte, Mark Lautens
Summary: A palladium-catalyzed strategy has been proposed for synthesizing unsymmetrically linked heterocycles within stereoselective tetrasubstituted olefins, with high yields and excellent stereoselectivities achieved using low catalyst loadings. Mechanistic studies suggest a syn-carbopalladation of the carbamoyl chloride followed by Pd-II-catalyzed cyclization of alkyne-tethered nucleophiles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Christina Jaeger, Mona Haase, Katja Koschorreck, Vlada B. Urlacher, Jan Deska
Summary: Biocatalytic oxidation of acylated hydroxylamines enables selective introduction of nitrogen functionalities by activating allylic C-H bonds. Utilizing laccases or oxidase/peroxidase couple with air as the oxidant, acylnitroso species are generated under mild aqueous conditions. These reactive intermediates undergo C-N bond formation through an ene-type mechanism, providing high yields in both intramolecular and intermolecular enzymatic aminations. Investigations on different pathways and labelling studies provide insight into the promiscuity of oxidoreductases as catalysts for nitroso-based transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Medicine, Research & Experimental
Akhilesh, Ankit Uniyal, Anagha Gadepalli, Vineeta Tiwari, Meghana Allani, Deepak Chouhan, Obulapathi Ummadisetty, Nimisha Verma, Vinod Tiwari
Summary: Chemotherapy-induced neuropathic pain (CINP) is a common clinical complication associated with anti-cancer drugs, affecting nearly 68.1% of cancer patients undergoing chemotherapy. The involvement of TRPV1 in CINP signaling suggests that targeting this nociceptor with siRNA may provide effective therapeutic interventions for managing CINP.
Article
Biochemistry & Molecular Biology
Shivani Jaiswal, Akhilesh, Ankit Uniyal, Vinod Tiwari, Senthil Raja Ayyannan
Summary: Researchers have discovered a promising lead compound for the treatment of neuropathic pain by designing and synthesizing a series of compounds. The lead compound exhibited potent inhibition activity against both FAAH and MAGL, and showed good safety profile in vivo experiments.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Immunology
Ankit Uniyal, Akhilesh, Aaina Singh Rathore, Priyanka Kumari Keshri, Surya Pratap Singh, Sanjay Singh, Vinod Tiwari
Summary: This study suggests that inhibition of pan-Aurora kinase can effectively inhibit evoked and chronic ongoing pain in nerve-injured rats by reducing KIF-17 mediated NR2B activation.
INTERNATIONAL IMMUNOPHARMACOLOGY
(2022)
Review
Endocrinology & Metabolism
Shivangi Patel, Dilip Sharma, Ankit Uniyal, Akhilesh, Anagha Gadepalli, Vinod Tiwari
Summary: This article discusses the biomarkers of schizophrenia, with a focus on diagnostic, therapeutic, and prognostic biomarkers. The findings can contribute to the prevention and treatment of schizophrenia.
METABOLIC BRAIN DISEASE
(2022)
Article
Immunology
Ankit Uniyal, Anagha Gadepalli, Ajay Modi, Vinod Tiwari
Summary: Chronic pain is a burdensome disorder affecting millions of people worldwide, and recent studies have revealed the important role of kinesin nanomotors. In an animal model, the aurora kinase inhibitor tozasertib can alleviate acute inflammatory pain and suppress hypersensitivity to different stimuli. Further investigations demonstrate that tozasertib can also attenuate oxidative stress and immune cell activation induced by chronic pain. These findings suggest that tozasertib exerts its anti-nociceptive effects by inhibiting the aurora kinase-mediated signaling.
INFLAMMOPHARMACOLOGY
(2022)
Review
Nanoscience & Nanotechnology
Saurabh Shah, Paras Famta, Vinod Tiwari, Arun K. Kotha, Rama Kashikar, Mahavir Bhupal Chougule, Young Hun Chung, Nicole F. Steinmetz, Mohammad Uddin, Shashi Bala Singh, Saurabh Srivastava
Summary: This article reviews and discusses the interplay between tumor microenvironment and the immunological cascade and how it can be utilized to develop nanoparticle-based cancer vaccines and immunotherapies. Nanoparticles and proteinaceous vaccines have enormous potential in cancer therapy.
WILEY INTERDISCIPLINARY REVIEWS-NANOMEDICINE AND NANOBIOTECHNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Priyanka Bose, Manoj K. Jaiswal, Sumit K. Singh, Rakesh K. Singh, Vinod K. Tiwari
Summary: In nature, glycan chains called sialic acids or nuraminic acids cover most cells and have long been recognized for their therapeutic importance. Sialic acid-containing glycans play a crucial role on cell surfaces, modulating and mediating various cellular interactions. Understanding the interaction between sialo-proteins and their roles in vertebrates has had a significant impact on medicine.
CARBOHYDRATE RESEARCH
(2023)
Article
Pharmacology & Pharmacy
Shivani Jaiswal, Vinod Akhilesh, Vinod Tiwari, Senthil Raja Ayyannan
Summary: The isatin-derived carbohydrazone, SIH 3, showed significant anti-nociceptive activity in the neuropathic pain model without altering locomotor activity. It also displayed excellent safety profile in acute oral toxicity study and exhibited antioxidant effect in oxidative stress induced by chronic constrictive injury.
PHARMACOLOGICAL REPORTS
(2023)
Article
Chemistry, Organic
Sunil Kumar, Mangal S. Yadav, Sumit K. Singh, Sanchayita Rajkhowa, Vinod K. Tiwari
Summary: A modular and reliable click approach was used to synthesize lactose- and galactose-coated calixarenecored G(1) and G(2) generation glycodendrimers efficiently. The characterization of the developed calixarene glycodendrimers was performed using extensive spectral analysis including NMR (H-1 and C-13), MS, IR, and SEC data.
Article
Biochemistry & Molecular Biology
Priyanka Bose, Anand K. Agrahari, Rajan Singh, Mala Singh, Sunil Kumar, Rakesh K. Singh, Vinod K. Tiwari
Summary: A click-inspired piperazine glycoconjugate was developed to synthesize water-soluble and biocompatible motifs. This study focused on designing and synthesizing versatile sugar-appended triazoles using "Click Chemistry", and evaluated their pharmacological properties on cyclin-dependent kinases (CDKs) and cytotoxicity on cancer cells through in silico and in vitro approaches, respectively. The galactose- and mannose-derived piperazine conjugates were identified as promising motifs. The galactosyl bis-triazolyl piperazine analogue 10b was found to be the most interactive with CDKs and showed significant anticancer activity.
CARBOHYDRATE RESEARCH
(2023)
Review
Chemistry, Multidisciplinary
Manoj K. Jaiswal, Vinod K. Tiwari
Summary: Click Chemistry is a modular, rapid, and reliable tool used for the regioselective 1,2,3-triazole forming [3+2] reaction of organic azide and terminal alkyne. It is widely explored in various emerging research domains. The intramolecular click chemistry, which involves metal-catalyzed cyclization, organo-catalyzed cyclization, and thermal-induced topochemical reaction, is less addressed compared to the intermolecular metal variant. Recent approaches on intramolecular azide-alkyne cycloaddition 'Click Chemistry' and their emerging applications in the development of diverse molecules are reported.
Article
Chemistry, Multidisciplinary
Manoj K. Jaiswal, Abhishek Gupta, Mangal S. Yadav, Vinay K. Pandey, Vinod K. Tiwari
Summary: A novel organocatalyzed [3+2] cycloaddition reaction has been developed for the construction of 1,5-disubstituted triazolyl glycoconjugates. The reaction involves the use of Schreiner thiourea organocatalysts to activate nitroolefins through double hydrogen bonding. This metal-free and acid-free synthetic protocol is operationally simple, regioselective, and complements the classical RuAAC catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles. By using catalytic amounts of the Schreiner thiourea organocatalyst, a wide range of organic azides can react with nitroolefins to produce diverse 1,5-disubstituted 1,2,3-triazoles in good yields with excellent regioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Sumit K. Singh, Sunil Kumar, Mangal S. Yadav, Abhishek Gupta, Vinod K. Tiwari
Summary: This report describes a convenient method for the Cu(I)-catalyzed Sonogashira cross-coupling reaction of aryl/heteroaryl halides and alkynyl sugars using a glycohybrid ligand. The method has notable features, including low catalytic loading, cost-effectiveness, and a wide substrate scope.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sumit K. Singh, Sunil Kumar, Mangal S. Yadav, Subrato Bhattacharya, Vinod K. Tiwari
Summary: This report describes a convenient Cu(I)-catalyzed tandem synthesis method for the efficient synthesis of dihydrophenanthridinediones and substituted isoquinolinones using glycosyl 1,2,3-triazole-based pyridinamide ligands. The method successfully forms biologically relevant heterocyclic scaffolds in high yields through intermolecular C-C cross-coupling followed by intramolecular cyclization. Notable features of this method include low catalytic loading, use of cost-effective and biocompatible ligands, high reaction yield, and easily accessible starting materials, making it a versatile protocol.
SYNTHESIS-STUTTGART
(2023)
Review
Chemistry, Organic
Mangal S. Yadav, Abhishek Gupta, Priyanka Bose, Anoop S. Singh, Prabhu P. Mohapatra, Vinod K. Tiwari
Summary: N-Acylbenzotriazoles are important synthons in organic synthesis and can serve as alternative acylating agents in various organic transformations. This review summarizes the preparation methods of N-Acylbenzotriazole derivatives and their diverse applications, highlighting their ability to conveniently synthesize biologically important organic compounds as alternative acylating agents. The significance of using benzotriazole ring cleavage methodology in compound synthesis is also emphasized.
