Article
Chemistry, Applied
Mohammad Taghi Nazeri, Siamak Javanbakht, Mohadese Nabi, Ahmad Shaabani
Summary: In this study, pectin was used as a green support to construct an efficient heterogeneous catalytic system based on metal phthalocyanines. The catalytic activity of the copper phthalocyanine-conjugated pectin in the CO2 fixation reaction was investigated. Pectin successfully improved the catalytic properties of the Cu-PcTA.
CARBOHYDRATE POLYMERS
(2022)
Review
Biochemistry & Molecular Biology
Seyyed Emad Hooshmand, Wei Zhang
Summary: The Ugi four-component reaction (Ugi-4CR) is a highly influential multicomponent reaction that has been widely used in the synthesis of diverse heterocycle molecules. It involves the use of amine, aldehyde or ketone, isocyanide, and carboxylic acid to produce α-acetamido carboxamide derivatives, significantly advancing the field of isocyanide-based multicomponent reactions. Alternative reagents for the components have been explored, making the Ugi reaction a versatile method for the synthesis of biologically active molecules and complex scaffolds. This review focuses on the use of alternative components in Ugi multicomponent reactions, particularly over the past decade.
Article
Chemistry, Organic
Chao Liu, Liangliang Song, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel method utilizing a combination of Ugi-4CR and sequential C-S/C-N bond cleavage has been developed to prepare diverse peptidomimetics containing a primary amide in a rapid, efficient, and cost-effective manner. The approach demonstrates high yield, excellent chemoselectivity, and tolerance towards various functional groups. Compounds derived from pharmaceuticals and beta-amino acids were successfully prepared, suggesting a new direction for peptidomimetic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Chih-Yu Wu, Sivan Perumal Murugan, Yu-Wei Wang, Hao-Wei Pan, Bing-Jian Sun, Yu-Ting Lin, Siti Fatimah, Agnes H. H. Chang, Chinpiao Chen, Gene-Hsian Lee
Summary: This study developed an efficient method for preparing diastereo- and regio-selective indoline-fused 2,5-diketopiperazine scaffolds using Ugi reaction and a post-Ugi tandem reaction under basic conditions. The possible reaction mechanism and substrate structures were elucidated through single-crystal X-ray diffraction analysis and density functional theory calculations.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Camilla Russo, Rolando Cannalire, Paolo Luciano, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano
Summary: A new visible-light photocatalytic multicomponent reaction has been developed for the synthesis of 1,3,4-oxadiazole derivatives, with good functional group tolerance and a broad substrate scope. Additionally, a two-step one-pot protocol for the synthesis of non-symmetrical diacylhydrazines has been reported. This method is particularly useful for late-stage functionalization of amino acids and drugs.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Mohammad Taghi Nazeri, Maryam Ghasemi, Masoomeh Ahmadi, Ahmad Shaabani, Behrouz Notash
Summary: By employing triazolobenzodiazepine as a cyclic imine, a variety of compounds can be synthesized under different reaction conditions, with mild conditions and high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Monu Agarwal, Kanchan Verma, Gargi Pathak, Sakshi Pathak, Jaya Mathur, Mahendra Kumar
Summary: This review discusses recent advances in the synthesis of structurally and functionally diversified quinoxalines-drug-like small molecules. It also focuses on the research work on isocyanide-based multicomponent reactions. These synthetic methods provide access to a wide range of natural product mimetic scaffolds using isocyanide-based combinatorial synthesis, which is significant for the synthesis of complex bioactive natural products and potential synthetic pharmaceuticals.
Article
Chemistry, Organic
Mohammad Taghi Nazeri, Ali Beygzade Nowee, Siamak Javanbakht, Hassan Farhid, Ahmad Shaabani, Behrouz Notash
Summary: Recent studies have shown that the combination of different bioactive scaffolds in a structure can create modern drugs/compounds with unique synergistic biological properties. This study describes the synthesis of tetrazole bearing sulfonamide compounds through the engagement of sulfonamides in the Ugi tetrazole reaction, with high atom economy and product yields. The use of group-assisted purification (GAP) chemistry avoids traditional purification methods, and theoretical docking studies provide insights into the potential biological activity and binding interactions of the synthesized compounds with human serum albumin.
Article
Chemistry, Organic
Oleksandr Kolomiiets, Alexander Tsygankov, Maryna N. Kornet, Aleksander A. Brazhko, Vladimir I. Musatov, Valentyn A. Chebanov
Summary: Peptidomimetics with a substituted imidazo[1,2-a ]pyridine fragment were synthesized using a combination of Groebke-Black-burn-Bienayme and Ugi reactions. The resulting products contained substituted imidazo[1,2-a]pyridine and peptidomimetic moieties as pharmacophores, with four diversity points introduced from readily available starting materials. A focused compound library consisting of 20 Ugi products was prepared and screened for antibacterial activity.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Environmental Sciences
Qi Liu, Guo-Long Zang, Quan Zhao
Summary: In this study, UiO-66-NH2 and UiO-66-NS were prepared for efficient removal of methyl orange. UiO-66-NS showed good adsorption performance and exhibited high stability under different environmental conditions.
ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Chandra S. Azad, Pratibha Shukla, Mark A. Olson, Anudeep K. Narula
Summary: A catalytic two-component three-centered (2C3C) Ugi-type reaction was developed for the synthesis of L-1-deoxynojirimycin (DNJ) isomers using a chiron approach, with high yields achieved for both L-allo-DNJ and L-altro-DNJ.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yanira Mendez, Aldrin V. Vasco, Galway Ivey, Ana Laura Dias, Peter Gierth, Barbara B. Sousa, Claudio D. Navo, Angel Torres-Mozas, Tiago Rodrigues, Gonzalo Jimenez-Oses, Goncalo J. L. Bernardes
Summary: A novel multicomponent approach combining the isonitrile-tetrazine (4+1) cycloaddition and the Ugi four-component reaction was developed to generate pyrazole amide derivatives. The scope of the reaction and the mechanistic insights of the 4H-pyrazol-4-imine tautomerization were provided. This multicomponent process expands the chemical space of pyrazole amide derivatives and offers a tool for peptide modification and stapling.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Sirous Haghipour, Morteza Mehrdad, Samanesadat Hosseini, Ali Moazzam, Kourosh Rad-Moghadam, Mohammad Mahdavi
Summary: This paper describes the development of a compound called 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, which acts as a heterocyclic enol containing a Michael acceptor and participates in a multicomponent condensation through a Smiles rearrangement. The four-component reaction involving this compound, aldehyde derivatives, amine derivatives, and isocyanides leads to the formation of heterocyclic enamines in a facile and efficient manner. This study presents an excellent strategy for synthesizing new biologically active compounds with quinolin-2(1H)-one scaffolds.
MOLECULAR DIVERSITY
(2023)
Review
Chemistry, Multidisciplinary
Jian Luo, Guo-Shu Chen, Shu-Jie Chen, Zhao-Dong Li, Yun-Lin Liu
Summary: This review discusses the recent advancements in catalytic enantioselective isocyanide-based reactions, highlighting the advantages, limitations, possible mechanisms, and synthetic applications of each reaction type. Additionally, it provides a personal outlook on potential opportunities for further exploration in this rapidly growing field.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Agriculture, Multidisciplinary
Lorena L. Mendes, Jodieh O. S. Varejao, Jose Antonio de Souza, Jose Walkimar de M. Carneiro, Ana K. S. M. Valdo, Felipe T. Martins, Bruno W. Ferreira, Robert W. Barreto, Toshik da Silva, Markus Kohlhoff, Eduardo J. Pilau, Eduardo V. V. Varejao
Summary: Experimental findings indicated that the presence of bulky substituents at the ortho position of a benzene ring hindered the synthesis of 2,5-DKPs, while bromine as a leaving group was more effective than chlorine in lowering the activation enthalpy for cyclization step, promoting the formation of 2,5-DKPs.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Sandra Gorska, Anna Maksymiuk, Jadwiga Turlo
Summary: Selenosugars are a diverse group of sugar derivatives with potential biological and pharmacological activities, including antitumor, immune-enhancement, and antioxidant effects. The synergy between selenium and polysaccharides in Se-polysaccharides may lead to enhanced pharmacological properties for applications in various health-related benefits.
APPLIED SCIENCES-BASEL
(2021)
Article
Biochemistry & Molecular Biology
Sandra Gorska-Jakubowska, Marzenna Klimaszewska, Piotr Podsadni, Beata Kaleta, Radoslaw Zagozdzon, Sabina Gorska, Andrzej Gamian, Tomasz Straczek, Czeslaw Kapusta, Marcin Cieslak, Julia Kazmierczak-Baranska, Barbara Nawrot, Jadwiga Turlo
Summary: The selenium-enriched polysaccharides from fungal sources exhibit immunomodulatory and antioxidant activities, enhancing cell viability and inhibiting the proliferation of human peripheral blood mononuclear cells, but with lower activity compared to selenium-containing mycelial isolates.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Medicinal
Roberto Fino, Dominik Lenhart, Vishal C. Kalel, Charlotte A. Softley, Valeria Napolitano, Ryan Byrne, Wolfgang Schliebs, Maciej Dawidowski, Ralf Erdmann, Michael Sattler, Gisbert Schneider, Oliver Plettenburg, Grzegorz M. Popowicz
Summary: This study aims to discover and develop new potential compounds to treat trypanosomiasis by targeting the PEX14-PEX5 interaction through the synergy between structural biology, computer-aided drug design, and medicinal chemistry.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2021)
Review
Medicine, General & Internal
Lidia Rudnicka, Malgorzata Olszewska, Mohamad Goldust, Anna Waskiel-Burnat, Olga Warszawik-Hendzel, Przemyslaw Dorozynski, Jadwiga Turlo, Adriana Rakowska
Summary: This review discusses the efficacy and safety differences of preparations containing calcipotriol combined with betamethasone dipropionate in treating different types of psoriasis. Foams are more effective in plaque psoriasis, while gels or ointments are preferred for scalp or nail psoriasis respectively. Overall, the safety profiles of foams, ointments, and gels are comparable, with pruritus being the most common adverse effect.
JOURNAL OF CLINICAL MEDICINE
(2021)
Article
Biochemistry & Molecular Biology
Beata Kaleta, Aleksander Roszczyk, Michal Zych, Monika Kniotek, Radoslaw Zagozdzon, Marzenna Klimaszewska, Eliza Malinowska, Michal Pac, Jadwiga Turlo
Summary: The study revealed the significant immunosuppressive activity of the Lentinula edodes-derived Se-Le-30 fraction on human immune cells, showing inhibition of proliferation in PBMCs, down-regulation of inflammatory cytokine production in T cells, and reduction in cytotoxicity of NK cells.
Article
Environmental Sciences
Agata Sosnicka, Bartosz Kozka, Katerina Makarova, Joanna Giebultowicz, Marzenna Klimaszewska, Jadwiga Turlo
Summary: White-rot fungi have the ability to degrade various environmental pollutants, including pharmaceuticals. However, conventional wastewater treatment methods are not efficient in removing these contaminants. This study aims to find low-cost culture media for fungal cultures to optimize biomass production and enzyme activity. The results show that certain media variants composed of agricultural byproducts can promote fungal growth and enzyme production. Additionally, the study demonstrates the potential of using Pleurotus ostreatus in corn steep liquor medium to remove drug contaminants from water.
Review
Biochemistry & Molecular Biology
Aleksander Roszczyk, Jadwiga Turlo, Radoslaw Zagozdzon, Beata Kaleta
Summary: Shiitake mushroom, also known as Lentinula edodes, is a popular edible fungus that contains valuable polysaccharides with anticancer, antioxidant, antimicrobial, and immunomodulatory properties. The biological activity of these polysaccharides depends on the extraction method.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Medicinal
Valeria Napolitano, Piotr Mroz, Monika Marciniak, Vishal C. Kalel, Charlotte A. Softley, Julian D. Janna Olmos, Bettina G. Tippler, Kenji Schorpp, Sarah Rioton, Tony Froehlich, Oliver Plettenburg, Kamyar Hadian, Ralf Erdmann, Michael Sattler, Grzegorz M. Popowicz, Maciej Dawidowski, Grzegorz Dubin
Summary: Trypanosomiases are neglected tropical diseases caused by Trypanosoma (sub)species. The inhibition of the PEX5-PEX14 protein-protein interaction has shown potential as a lethal treatment for Trypanosoma. Researchers have developed a novel compound scaffold that inhibits PEX5-PEX14 PPI and has demonstrated trypanocidal activity in cell-based assays.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Aleksander Roszczyk, Michal Zych, Katarzyna Zielniok, Natalia Krata, Jadwiga Turlo, Marzenna Klimaszewska, Radoslaw Zagozdzon, Beata Kaleta
Summary: The polysaccharides isolated from Lentinula edodes, particularly the Se-Le-30 fraction, have shown immunomodulatory effects on human T lymphocytes by inhibiting proliferation of CD3-stimulated T cells and enhancing cytokine synthesis. These findings suggest the potential use of Se-Le-30 as a therapeutic compound in immunomodulation research.
Article
Chemistry, Medicinal
Piotr Stepnicki, Katarzyna M. Targowska-Duda, Anton L. Martinez, Agata Zieba, Olga Wronikowska-Denysiuk, Martyna Z. Wrobel, Agata Bartyzel, Alicja Trzpil, Tomasz M. Wrobel, Andrzej Chodkowski, Karolina Mirecka, Tadeusz Karcz, Katarzyna Szczepanska, Maria I. Loza, Barbara Budzynska, Jadwiga Turlo, Jadwiga Handzlik, Emilia Fornal, Ewa Poleszak, Marian Castro, Agnieszka A. Kaczor
Summary: Schizophrenia is a complex mental disorder involving various neurotransmitter systems. Antipsychotics can be divided into classical drugs and atypical antipsychotics, the latter of which have a multi-target profile affecting both dopamine and serotonin receptors. This profile is considered more effective and safer in treating symptoms.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Piotr Stepnicki, Olga Wronikowska-Denysiuk, Agata Zieba, Katarzyna M. Targowska-Duda, Agata Bartyzel, Martyna Z. Wrobel, Tomasz M. Wrobel, Klaudia Szalaj, Andrzej Chodkowski, Karolina Mirecka, Barbara Budzynska, Emilia Fornal, Jadwiga Turlo, Marian Castro, Agnieszka A. Kaczor
Summary: The study aims to find new antipsychotics by optimizing the compound D2AAK3, a multi-target ligand of G-protein-coupled receptors (GPCRs). Compounds 1 and 10 were selected based on their receptor profile and evaluated for their antipsychotic activity, as well as their effects on memory and anxiety processes. Molecular modelling and X-ray study were conducted to investigate the interactions and stable conformation of the compounds.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Monika Marciniak, Piotr Mroz, Valeria Napolitano, Vishal C. Kalel, Roberto Fino, Emilia Pykacz, Wolfgang Schliebs, Oliver Plettenburg, Ralf Erdmann, Michael Sattler, Grzegorz M. Popowicz, Maciej Dawidowski
Summary: Protein-protein interactions (PPIs) are important targets for small molecule drugs, but can be challenging to inhibit. In this study, a new class of peptidomimetic scaffolds was developed to target the PEX5-PEX14 PPI, which plays a critical role in glycosome biogenesis and is a potential target for drugs against Trypanosoma infections. The designed peptidomimetics inhibited the PEX5-TbPEX14 PPI and exhibited cellular activity against T. b. brucei, providing a promising approach for the development of trypanocidal agents and helical mimetics as PPI inhibitors.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Nutrition & Dietetics
Malgorzata Kalucka, Aleksander Roszczyk, Marzenna Klimaszewska, Beata Kaleta, Ewelina Drelich, Anna Blazewicz, Sandra Gorska-Jakubowska, Eliza Malinowska, Marek Krol, Aleksandra Maria Prus, Katarzyna Trzesniowska, Aleksandra Wolczynska, Przemyslaw Dorozynski, Radoslaw Zagozdzon, Jadwiga Turlo
Summary: In this study, mycelial cultures of Lentinula edodes were used to obtain selenium-containing immunomodulatory preparations. The researchers also aimed to investigate the simultaneous accumulation of selenium and zinc in these mycelia. The effects of the selenium and zinc extracts on T cell activation in human PBMCs were studied, and significant changes were observed in the expression of PD-1 and CD25 antigens on CD8+ T cells. The selenium and zinc content in the preparations modified the immunomodulatory activity of mycelial polysaccharides, but the mechanisms of action of the active ingredients in the extracts were found to be different.
Article
Biochemistry & Molecular Biology
Martyna Z. Wrobel, Andrzej Chodkowski, Maciej Dawidowski, Agata Siwek, Katarzyna Stachowicz, Bernadeta Szewczyk, Gabriel Nowak, Grzegorz Satala, Andrzej J. Bojarski, Jadwiga Turlo
Summary: The synthesis and evaluation of new compounds targeting the serotonin 1A receptors and serotonin transporter in the treatment of central nervous system diseases, especially depression, were conducted. Compound 4f emerged as the most promising with good activity, stability, and potential as a therapeutic agent.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
