Article
Materials Science, Multidisciplinary
Meryem S. S. Akdemir, Birgit Huber, Marina Simian, Hatice Mutlu, Patrick Theato
Summary: The unique molecular structure of tetrazoles, consisting of a five-membered ring with four nitrogen atoms, has great potential in polymer chemistry. While research on tetrazole-containing polymers with pendant chains has been extensively studied, the synthesis of main chain tetrazole-based polymers has not been widely explored. This study demonstrates the possibility of polymer formation using the Ugi-azide-four-multicomponent polymerization strategy for main chain 1,5-disubstituted-1H-tetrazole-based compounds. The synthesized polymers displayed interesting properties such as adjustable glass-transition temperature and thermal stability.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Organic
Negin Dehghan, Hossein Nasr-Isfahani, Afshin Sarvary, Mohammad Bakherad
Summary: The study describes a double four component Azido-Ugi reaction involving isocyanide, TMSN3, aldehyde, and 4,4'-sulfonyldianiline with two amine functional groups in MeOH at 65 degrees C. It reports the synthesis of pharmacologically and structurally interesting compounds with two 1,5-disubstituted tetrazole rings from available and inexpensive reagents using a convenient process and mild reaction conditions. Modifications in the structure of the reaction product could be achieved by varying the aldehyde or isocyanide component, with the products being characterized by Mass, H-1 NMR, and C-13 NMR spectral studies as new.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Polymer Science
Meryem S. Akdemir, Marina Simian, Patrick Theato, Hatice Mutlu
Summary: Nitrogen-rich functional groups like tetrazole and its derivatives have gained increasing interest in the chemistry of small molecules. Nitrogen-decorated polymers have attracted attention for potential biomedical applications due to their diverse biological properties. A new synthesis route combining Ugi-azide four-multicomponent reaction and thiol-ene polymerization has been reported for the synthesis of nitrogen-decorated polymers. The synthesized polymers demonstrate high apparent number average molecular mass and have been characterized for their chemical, thermal, and optical properties.
MACROMOLECULAR CHEMISTRY AND PHYSICS
(2023)
Article
Chemistry, Medicinal
Fausta Ulgheri, Pietro Spanu, Francesco Deligia, Giovanni Loriga, Maria Pia Fuggetta, Iris de Haan, Ajay Chandgudge, Matthew Groves, Alexander Domling
Summary: Using a mixed modelling, computational screening, synthesis and in vitro testing approach, a novel class of non-covalent caspase-1 inhibitors was identified. These inhibitors effectively inhibit IL-1 beta release in activated macrophages, showing potential for the treatment of inflammation and inflammatory diseases.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Cesia M. Aguilar-Morales, Jorge Gustavo Araujo-Huitrado, Yamile Lopez-Hernandez, Claudia Contreras-Celedon, Alejandro Islas-Jacome, Angelica Judith Granados-Lopez, Cesar R. Solorio-Alvarado, Jesus Adrian Lopez, Luis Chacon-Garcia, Carlos J. Cortes-Garcia
Summary: This study presents a high-order multicomponent reaction to obtain novel linked 1,5-disubstituted tetrazole-1,2,3-triazole hybrids in low to moderate yield. The cascade process involves Ugi-azide, bimolecular nucleophilic substitution (S(N)2), and copper-catalyzed alkyne-azide reaction (CuAAC), forming six new bonds. The synthesized hybrid compounds show potential as drug candidates for breast cancer treatment, especially those with cyclohexane and halogens in their structures, although further assays are needed to fully understand their effects on cancer cell hallmarks.
Article
Chemistry, Multidisciplinary
Thomas R. R. Roose, H. Daniel Preschel, Helena Mayo Tejedor, Jasper C. C. Roozee, Trevor A. A. Hamlin, Bert U. W. Maes, Eelco Ruijter, Romano V. A. Orru
Summary: An iron-catalysed carbene transfer reaction of diazo compounds to isocyanides has been developed, allowing the synthesis of densely functionalized heterocycles in a one-pot process. The reaction provides a cost-efficient and benign alternative to noble metal-catalysed processes. DFT calculations provide insights into the reaction mechanism.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Israel Nino-Pantoja, Arturo Gallardo-Alfonzo, Melchor Solis-Santos, Mario Ordonez, Claudia Contreras-Celedon, Alejandro Islas-Jacome, Luis Chacon-Garcia, Carlos J. Cortes-Garcia
Summary: A novel bis-heterocyclic system containing 1,2-dihydro-3H-pyrrolo[3,4-b]indolizin-3-one and 1,5-disubstituted tetrazole moieties was designed and synthesized as a Copper (II) recognizing agent. The compounds were prepared using a novel one-pot synthetic strategy involving four-step reactions. The photophysical properties of the obtained compounds were evaluated for their response to Copper (II).
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bidong Zhang, Katarzyna Kurpiewska, Alexander Domling
Summary: This paper describes a simple and short synthesis method for the privileged scaffold dihydropyrrolo[1,2-a]pyrazine-dione, a compound with potential bioactivity, using readily accessible starting materials and a multicomponent reaction-based protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Joanna Bojarska, Martin Breza, Milan Remko, Ye Yuan, Zyta M. Ziora, Tsun-Thai Chai, Izabela D. Madura, Krzysztof Kaczmarek, Mark A. T. Blaskovich, Wojciech M. Wolf
Summary: A supramolecular behavior of a newly synthesized compound and a library of tetrazole-based H-bonding synthons were studied by X-ray crystallography and computational techniques. The supramolecular assembly was controlled by various interactions, including O...H, N...H, C...H, and pi-stacking interactions. The 3D topologies of the supramolecular architectures were visualized and dispersion forces played a crucial role. Quantum-chemical treatment revealed the chemical activity and stability of the compound. These findings provide valuable information for the design of therapeutic agents containing tetrazole motifs.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Applied
Hamidreza Younesi, Sakineh Asghari, Ghasem Firouzzadeh Pasha, Mahmood Tajbakhsh
Summary: In this study, a multi-component reaction was used to modify the surface of nano zeolite, resulting in high functionality. The Ugi reaction was applied for the first time to develop a hydrogen-bonding nanocatalyst by post-modifying nano NaY zeolite with 3-aminopropyltriethoxysilane (APTES) and then reacting it with salicylaldehyde, tert-butyl isocyanide, and acetic acid. The modified nano zeolite showed improved reactivity, dispersibility, and hydrogen bonding formation capability. The nanocatalyst was characterized using various techniques and exhibited excellent catalytic activity in a three-component reaction. The catalyst could be easily separated and reused multiple times without significant activity loss, making this eco-friendly method suitable for the preparation of other important heterocyclic compounds.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrey Bubyrev, Ksenia Malkova, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin
Summary: A three-component synthesis of 1,5-disubstituted 1,2,3-triazoles can be achieved from alpha-acetyl-alpha-diazomethane sulfonamides, primary aliphatic amines, and aromatic aldehydes. The synthesis can proceed in two alternative variants based on the substitutions in the diazo reagent. Depending on the variant, the intermediates are either isolated and subjected to aromatization, or both transformations take place in a single step at room temperature.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Chante Summers, Christopher Perry, Whitney Friederich, Katlyn Hausman, Sarah B. Luesse
Summary: A one-pot tandem route to functionalized 2,5-disubstituted furans has been developed, with the unexpected discovery of a furyl cation-driven skeletal rearrangement. The choice of 2-furaldehyde or 2-nitrophenol component determines whether the standard Passerini-Smiles reaction is followed by rearrangement to produce a rearranged PS-R product. The rearrangement has been confirmed through isolation of the PS product and subsequent conversion to the PS-R product via microwave irradiation.
Article
Chemistry, Multidisciplinary
Chao Liu, Liangliang Song, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A transition metal-free method for C-S bond cleavage and Mannich reaction of Ugi-adducts with alcohols and thiols has been developed, leading to the synthesis of diverse novel peptidomimetics containing N,O- or N,S-aminals. This method exhibits exclusive selectivity, broad substrate scope, excellent yield, and tolerance towards different functional groups, and has been successfully applied to substrates derived from pharmaceuticals febuxostat, probenecid, and memantine.
Article
Chemistry, Organic
Hong Zhang, Kris Depew, Jean-Francois Chiasson, Chun Yuen Leung, Sheldon N. Crane, Matthew Rhodes, Zhihua Sui, Peng Liu
Summary: A highly efficient synthesis has been developed for the direct access of 2,3-disubstituted 4H-pyrido[1,2-a] pyrimidin-4-ones from N-pyridoketenimine precursors. The ketenimine intermediates react efficiently with N-, S-, O- and C-nucleophiles, providing the corresponding disubstituted pyridopyrimidinone products in good yields. This method is simple and avoids the use of transition metals, allowing for rapid assembly of this structural motif for SAR studies and late stage process development.
Article
Chemistry, Multidisciplinary
Ping Wang, Baozhong Zhang
Summary: This study investigated the impact of disubstitution patterns on the physical properties and processing characteristics of indole-based aromatic polyesters. New monomers and polyesters with enhanced thermal stability were synthesized, showing tunable glass transition temperatures and improved solution crystallization. Additionally, the new polyesters could be crosslinked with sustainable aromatic aldehyde to further enhance their thermal properties.
Article
Chemistry, Organic
Eman M. M. Abdelraheem, Samad Khaksar, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Shabnam Shaabani, Alexander Domling
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Eman M. M. Abdelraheem, Shabnam Shaabani, Alexander Domling
Article
Chemistry, Applied
Ahmad Shaabani, Adina Rashidi Vahid, Shabnam Shaabani, Reza Mohammadian, Mohammad Taghi Nazeri, Mina Keramati Nejad
APPLIED ORGANOMETALLIC CHEMISTRY
(2018)
Article
Chemistry, Medicinal
Shabnam Shaabani, Harmen P. S. Huizinga, Roberto Butera, Ariana Kouchi, Katarzyna Guzik, Katarzyna Magiera-Mularz, Tad A. Holak, Alexander Domling
EXPERT OPINION ON THERAPEUTIC PATENTS
(2018)
Article
Chemistry, Multidisciplinary
Yuanze Wang, Shabnam Shaabani, Maryam Ahmadianmoghaddam, Li Gao, Ruixue Xu, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Joe Olechno, Richard Ellson, Michael Kossenjans, Victoria Helan, Matthew Groves, Alexander Domling
ACS CENTRAL SCIENCE
(2019)
Article
Multidisciplinary Sciences
Constantinos G. Neochoritis, Shabnam Shaabani, Maryam Ahmadianmoghaddam, Tryfon Zarganes-Tzitzikas, Li Gao, Michaela Novotna, Tatiana Mitrikova, Atilio Reyes Romero, Marina Ika Irianti, Ruixue Xu, Joe Olechno, Richard Ellson, Victoria Helan, Michael Kossenjans, Matthew R. Groves, Alexander Domling
Article
Chemistry, Multidisciplinary
Angelina Osipyan, Shabnam Shaabani, Robert Warmerdam, Svitlana V. Shishkina, Harry Boltz, Alexander Domling
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Multidisciplinary Sciences
Fandi Sutanto, Shabnam Shaabani, Constantinos G. Neochoritis, Tryfon Zarganes-Tzitzikas, Pravin Patil, Ehsan Ghonchepour, Alexander Domling
Summary: The study demonstrates that multicomponent reactions are highly suitable for generating libraries of electrophiles based on different scaffolds and three-dimensional shapes, and are highly compatible with multiple functional groups. The operational procedure is simple, mild, and cost-effective, facilitating future covalent library synthesis.
Article
Chemistry, Multidisciplinary
Fandi Sutanto, Shabnam Shaabani, Rick Oerlemans, Deniz Eris, Pravin Patil, Mojgan Hadian, Meitian Wang, May Elizabeth Sharpe, Matthew R. Groves, Alexander Domling
Summary: This study demonstrates the interplay between high throughput synthesis and high throughput PX, showing the potential of this approach in early drug discovery and successfully yielding potent inhibitors of the COVID-19 causing agent.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Shabnam Shaabani, Louis Gadina, Ewa Surmiak, Zefeng Wang, Bidong Zhang, Roberto Butera, Tryfon Zarganes-Tzitzikas, Ismael Rodriguez, Justyna Kocik-Krol, Katarzyna Magiera-Mularz, Lukasz Skalniak, Alexander Domling, Tad A. Holak
Summary: Novel biphenyl-based chimeric compounds containing pomalidomide were found to exhibit strong inhibitory activity against PD-1/PD-L1, with compound 3 showing the best performance. Compounds 4 and 5 were able to significantly restore suppressed immunity in an ex vivo PD-1/PD-L1 blockade cell line bioassay.
Article
Chemistry, Multidisciplinary
Li Gao, Shabnam Shaabani, Atilio Reyes Romero, Ruixue Xu, Maryam Ahmadianmoghaddam, Alexander Doemling
Summary: We demonstrate the feasibility of synthesizing a large library based on 16 different chemistries in parallel on a nanoscale using highly automated methods. Unlike combinatorial chemistry, we generate 16 scaffolds simultaneously, with each compound produced through a random combination of diverse building blocks in a sparse matrix fashion. The advantages of this automated nanoscale synthesis approach include library diversity, absence of storage logistics, superior economics, faster synthesis through automation, increased safety, and sustainable chemistry.
Article
Biochemistry & Molecular Biology
Kai Gao, Shabnam Shaabani, Ruixue Xu, Tryfon Zarganes-Tzitzikas, Li Gao, Maryam Ahmadianmoghaddam, Matthew R. Groves, Alexander Domling
Summary: The study demonstrates the potential of on-the-fly compound synthesis and in situ screening in reducing the environmental footprint of medicinal chemistry. Acoustic dispensing technology was used to synthesize a library in a 1536 well format and screened against an oncogenic protein-protein interaction. Miniaturization and automation of the organic synthesis and screening process can accelerate early drug discovery as an alternative to traditional high throughput screening.
RSC MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mojgan Hadian, Shabnam Shaabani, Pravin Patil, Svitlana V. Shishkina, Harry Boeltz, Alexander Domling
Article
Chemistry, Multidisciplinary
Eman M. M. Abdelraheem, Imogen Goodwin, Shabnam Shaabani, Michel P. de Haan, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Domling
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Shabnam Shaabani, Ruixue Xu, Maryam Ahmadianmoghaddam, Li Gao, Martin Stahorsky, Joe Olechno, Richard Ellson, Michael Kossenjans, Victoria Helan, Alexander Domling
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
