Article
Chemistry, Organic
Ju Young Lee, Rohit Kumar Varshnaya, Eun Jeong Yoo
Summary: This study reported a copper-catalyzed [5+3] cycloaddition reaction for the synthesis of enantio-enriched diazocine derivatives. It was found that specific ligands and additives played significant roles in the catalytic process and preserved the induced stereoselectivity, demonstrating the potential applications of this asymmetric catalysis.
Review
Chemistry, Organic
Kristaps Leskovskis, Janis Mikelis Zakis, Irina Novosjolova, Maris Turks
Summary: Ring opening of purines can lead to the preparation of ring-modified purine derivatives, which are privileged molecular scaffolds in medicinal and agricultural chemistry. This approach is a useful alternative for their synthesis and can compete well with other methods.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Senka Djakovic, Ljubica Glavas-Obrovac, Jasmina Lapic, Silvija Maracic, Juraj Kirchofer, Marija Knezevic, Marijana Jukic, Silvana Raic-Malic
Summary: Conjugated uracil derivatives bridged by 1,2,3-triazole and containing mono-ferrocene or bis-ferrocene units were synthesized. The bis-ferrocenyl uracil derivatives showed better antiproliferative activities, especially on colon adenocarcinoma and Burkitt lymphoma cells, with potential targeting cancer cell mitochondria. This selective cytostatic effect may be attributed to mitochondrial membrane potential disruption and apoptosis induction.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Sarita Katiyar, Karthik Ramalingam, Abhishek Kumar, Alisha Ansari, Amol Chhatrapati Bisen, Garvita Mishra, Sachin Nashik Sanap, Rabi Sankar Bhatta, Bidyut Purkait, Neena Goyal, Koneni Sashidhara
Summary: A series of compounds were synthesized via molecular hybridization and examined for their inhibitory effects on intracellular amastigotes of Leishmania donovani. Compound 33 was identified as the most significant potential lead for future optimizations.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Seda Sirin, Halil Duyar, Belma Aslim, Zeynel Seferoglu
Summary: Novel compounds were synthesized and characterized in this study, showing antioxidant, acetylcholinesterase inhibition activity, and anti-proliferative effects on cancer cells. These compounds may serve as potential anti-cancer drug candidates for cancer treatment.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Multidisciplinary
Qiong Chen, Ye Lei, Guangcheng Wu, Qing Li, Yuanjiang Pan, Hao Li
Summary: In weakly acidic water, condensation of dihydrazide and cationic bisaldehyde compounds bearing polymethylene chains produces macrocycles or their dimers [2]catenanes. Addition of cucurbit[8]uril (CB[8]) shifts the equilibrium towards macrocycles by forming ring-in-ring complexes. Substitution of the polymethylene unit with a more rigid p-xylene linker leads to quantitative formation of [2]catenane. Addition of CB[8] transforms [2]catenane into an ultra-large macrocycle encircled by two CB[8] rings. Removal of CB[8] with a competitive guest leads to recovery of the [2]catenane.
Article
Biochemistry & Molecular Biology
Belma Zengin Kurt, Ozlem Altundag, Merve Nur Tokgoz, Dilek Ozturk Civelek, Fulya Oz Tuncay, Ummuhan Cakmak, Yakup Kolcuoglu, Atilla Akdemir, Fatih Sonmez
Summary: Fifteen novel flurbiprofen urea derivatives containing the thiadiazole ring were synthesized and tested for their inhibition effects on tyrosinase. Compound 3c was found to be the most potent inhibitor with an IC50 value of 68.0 μM. The synthesized compounds were also evaluated for their cytotoxic effects on different cancer cell lines, and 3l showed the highest cytotoxicity on HT-29 cells, 3o exhibited the strongest cytotoxic effect on HepG2 cells, and 3j strongly affected B16F10 cells.
CHEMICAL BIOLOGY & DRUG DESIGN
(2023)
Article
Biochemistry & Molecular Biology
Vincenzo Algieri, Paola Costanzo, Matteo Antonio Tallarida, Fabrizio Olivito, Antonio Jiritano, Giulia Fiorani, Francesca Peccati, Gonzalo Jimenez-Oses, Loredana Maiuolo, Antonio De Nino
Summary: This study reports the regioselective synthesis of a novel series of 1,5-disubstituted-1,2,3-triazole derivatives functionalized with pyrimidine nucleobases via 1,3-dipolar cycloaddition reaction. The synthesized compounds exhibited good pharmacokinetic properties and potential binding capabilities to viral and bacterial protein receptors based on molecular docking simulations.
Article
Chemistry, Organic
Michal Urban, Martin Nigrini, Ivana Cisarova, Jan Vesely
Summary: The atom-economic method developed using a chiral amine-squaramide Mannich reaction and Au(I)-catalyzed hydroamination can efficiently prepare novel bispirocyclic compounds containing three fused heterocyclic scaffolds. This synthetic strategy, whether performed stepwise or as a one-pot process, enables the formation of chiral bispirocyclic [oxindole-pyrrolidine-pyrazolones] with high yields (up to 75%) and excellent enantioselectivities (up to 99%).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Lak Shin Jeong, Young Eum Hyun, Seungchan An, Minjae Kim, In Guk Park, Sanghee Yoon, Hafiz Muhammad Ahmad Javaid, Thi Ngoc Lan Vu, Gyudong Kim, Hongseok Choi, Hyuk Woo Lee, Minsoo Noh, Joo Young Huh, Sun Choi, Hong-Rae Kim
Summary: Carbocyclic nucleosides with different sugar conformations were synthesized to study the effect of sugar puckering on binding to PPARs. All synthesized nucleosides showed binding affinity to PPAR gamma/delta, and their effect on adiponectin production correlated with their sugar conformation. (N)-conformer 3h was found to be the most potent PPAR delta antagonist with good adiponectin production, and it could inhibit the mRNA levels of LPS-induced IL-1 beta expression in RAW 264.7 macrophages, suggesting its anti-inflammatory activity.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Osamu Kubo, Kazuaki Takami, Masahiro Kamaura, Koji Watanabe, Hirohisa Miyashita, Shinichi Abe, Kae Matsuda, Yoshiyuki Tsujihata, Tomoyuki Odani, Shinji Iwasaki, Tomoyuki Kitazaki, Toshiki Murata, Kenjiro Sato
Summary: In this study, an optimization effort was conducted on a GPR119 agonist, resulting in the identification of a potent and orally bioavailable compound that enhanced insulin secretion in a diabetic animal model. The introduction of an N-trifluoromethyl group not only enhanced GPR119 agonist activity but also improved the hERG inhibition profile.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Physical
Karthik Rajagopal, Saravanan Dhandayutham, Manivannan Nandhagopal, Mathivanan Narayanasamy, Mohamed Elzagheid, Lydia Rhyman, Ponnadurai Ramasami
Summary: 4-Mercaptopyridylthiazole derivatives were synthesized using simple and eco-friendly reaction conditions. The compounds were characterized and tested for their biological activities. Among the tested compounds, 2-((2-(piperidin-1-yl)ethyl)thio)-4-(pyridin-4-yl)thiazole showed the best antifungal activity and low hemolytic activity.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Daniel K. Isika, Fatma Nur Ozkomec, Mustafa Cesme, Omowunmi A. Sadik
Summary: This study reports the synthesis and characterization of a novel class of flavonoid acetamide derivatives which improve the bioavailability and ADMET toxicity properties of flavonoids while decreasing their antioxidant activity.
Article
Chemistry, Organic
Sven Ole Jaeschke, Thisbe K. Lindhorst
Summary: By synthesizing xylose derivatives with high stereochemical precision and a high degree of functionalization, we have obtained molecules of interest as conformational hinge molecules and as orthogonally protected triamino scaffold molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Manu Kumar, Sang-Min Chung, Ganuskh Enkhtaivan, Rahul V. Patel, Han-Seung Shin, Bhupendra M. Mistry
Summary: Newly synthesized substituted benzothiazole based berberine derivatives demonstrated interesting anti-influenza virus activity, with BBD7 showing potent neuraminidase activity. Molecular docking analysis suggests that the antiviral mechanisms of these compounds may be similar to oseltamivir through interaction with residues of neuraminidase.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Applied
Denisa Hidasova, Radek Pohl, Ivana Cisarova, Ullrich Jahn
Summary: The study presents an asymmetric synthesis method for N,2,3,4,5-pentasubstituted pyrrolidines through oxidative single-electron transfer-catalyzed tandem reactions, enabling the diastereodivergent single-step synthesis of pyrrolidines with four contiguous stereogenic centers by setting the configuration of two stereocenters and generating two more in a selective manner. The stereoselectivity is rationalized by a predictive model.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Santiago Alonso-Gil, Kamil Parkan, Jakub Kaminsky, Radek Pohl, Takatsugu Miyazaki
Summary: Understanding the conformational changes in sugar moieties is important for studying glycoside hydrolase mechanisms and designing inhibitors. In this study, the conformational pathway of GH92 enzymes was predicted using computational methods and confirmed with experiments. The study also demonstrated the potential of a new type of C-disaccharides for biochemical applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Denise-Liu' Leone, Radek Pohl, Martin Hubalek, Marta Kaderabkova, Matous Kromer, Veronika Sykorova, Michal Hocek
Summary: Glyoxal-linked nucleotides were synthesized and used for efficient bioconjugations and crosslinking with arginine-containing peptides or proteins. The reactive glyoxal modification in DNA was found to be more reactive than previously reported 1,3-diketone-linked DNA probes.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biology
Yuliya Morozova, Iva Voborna, Radovan Zizka, Katerina Bogdanova, Renata Vecerova, Dominik Rejman, Milan Kolar, Duy Dinh Do Pham, Pavel Holik, Roman Mostek, Matej Rosa, Lenka Pospisilova
Summary: The study focused on the ex vivo effects of second- and third-generation LPPOs on Enterococcus faecalis in root canal samples, comparing them with other disinfectants. Results showed that LPPOs demonstrated superior bactericidal effects compared to the tested disinfectants by reducing planktonic bacterial cells and inhibiting biofilm formation.
Article
Chemistry, Multidisciplinary
Aswathi Chakrapani, Olatz Ruiz-Larrabeiti, Radek Pohl, Martin Svoboda, Libor Krasny, Michal Hocek
Summary: This study investigates the effects of glucosylation on DNA containing modified bases and its impact on transcription activity in bacteriophages or kinetoplastid parasites. The results show that glucosylation fully protects DNA from restriction endonuclease cleavage and while glucosylated 5hmU inhibits transcription, glucosylated 5hmC allows similar levels of transcription as natural DNA. Therefore, enzymatic glucosylation of 5hmC-containing DNA can be used to modulate transcription activity.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Zdenek Knejzlik, Michal Dolezal, Klara Herkommerova, Kamila Clarova, Martin Klima, Matteo Dedola, Eva Zbornikova, Dominik Rejman, Iva Pichova
Summary: This study reveals that guaB1 encodes a guanosine 5'-monophosphate reductase (GMPR) in the purine-salvage pathway, containing a cystathionine-beta-synthase domain (CBS) essential for enzyme activity. GMPR activity is regulated allosterically by the ATP/GTP ratio in a pH-dependent manner, with bioinformatic analysis suggesting the presence of GMPRs with CBS domains across the Actinobacteria phylum.
Article
Chemistry, Physical
Vladimir Palivec, Radek Pohl, Jakub Kaminsky, Hector Martinez-Seara
Summary: Determining the structure of saccharides in their native environment is crucial for understanding their function. In this study, we propose two cost-effective protocols for simulating sugar chemical shifts and recommend their use. These protocols not only help interpret experimental spectra, but can also independently predict structure.
JOURNAL OF CHEMICAL THEORY AND COMPUTATION
(2022)
Article
Chemistry, Medicinal
Duy Dinh Do Pham, Viktor Mojr, Michaela Helusova, Gabriela Mikusova, Radek Pohl, Eva Davidova, Hana Sanderova, Dragana Vitovska, Katerina Bogdanova, Renata Vecerova, Miroslava Htoutou Sedlakova, Radovan Fiser, Petra Sudzinova, Jiri Pospisil, Oldrich Benada, Tomas Krizek, Adela Galandakova, Milan Kolar, Libor Krasny, Dominik Rejman
Summary: The novel antibacterial compounds LEGO-LPPOs were developed based on LPPOs, showing activity against various bacteria with low cytotoxicity and resistance development potential. This new class of compounds demonstrates efficacy against multiresistant strains and persisters, by depleting membrane potential and creating pores in the cytoplasmic membrane.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Endocrinology & Metabolism
Josef Oeckl, Petra Janovska, Katerina Adamcova, Kristina Bardova, Sarah Brunner, Sebastian Dieckmann, Josef Ecker, Tobias Fromme, Jiri Funda, Thomas Gantert, Piero Giansanti, Maria Soledad Hidrobo, Ondrej Kuda, Bernhard Kuster, Yongguo Li, Radek Pohl, Sabine Schmitt, Sabine Schweizer, Hans Zischka, Petr Zouhar, Jan Kopecky, Martin Klingenspor
Summary: We explore different potential sources of UCP1-independent thermogenesis and identify a futile ATP-consuming triglyceride/fatty acid cycle as the main contributor to cellular heat production in brown adipocytes lacking UCP1. We uncover the mechanism on a molecular level and pinpoint the key enzymes involved using pharmacological and genetic interference.
MOLECULAR METABOLISM
(2022)
Article
Chemistry, Physical
Daisuke Sakamoto, Isabel Gay Sanchez, Jiri Rybacek, Jaroslav Vacek, Lucie Bednarova, Marketa Pazderkova, Radek Pohl, Ivana Cisarova, Irena G. Stara, Ivo Stary
Summary: This study describes an asymmetric synthesis method for the preparation of optically pure and conformationally locked oxabenzo[5]helicenes. These compounds can be transformed into cycloiridated organometallics and exhibit excellent catalytic performance in asymmetric transfer hydrogenation reactions.
Article
Chemistry, Multidisciplinary
Vaclav Houska, Egor Ukraintsev, Jaroslav Vacek, Jiri Rybacek, Lucie Bednarova, Radek Pohl, Irena G. Stara, Bohuslav Rezek, Ivo Stary
Summary: The synthesis of helically chiral macrocycles composed of dibenzo[5]helicene units and trans-stilbene-4,4'-diyl linkers is reported. Different stereoisomers of these macrocycles were obtained through chiral resolution. The self-assembly of these macrocycles into long 1D molecular stripes in ordered 2D nanocrystals was studied using AFM.
Article
Chemistry, Multidisciplinary
Vladimir Motornov, Radek Pohl, Blanka Klepetarova, Petr Beier
Summary: Elusive N-acyl-1,2,3-triazoles formed by direct acylation of NH-1,2,3-triazoles were isolated and characterized. Thermodynamic N2 isomers were found to be preferred. Direct evidence of interconversion between N1- and N2-acyltriazoles confirmed their usefulness in denitrogenative transformations. An efficient synthesis of enamido triflates from NH-triazoles via N2-acyl-1,2,3-triazole intermediates was developed.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
David Kodr, Erika Kuzmova, Radek Pohl, Tomas Kraus, Michal Hocek
Summary: We designed and synthesized lipid-modified dNTPs, which served as substrates for DNA polymerase and could be incorporated simultaneously into the DNA strand. These lipid-ON probes showed enhanced membrane anchoring efficiency and better stability in the cell membrane compared to commonly studied ON analogues. The probes were detected at the cell surface even after 24 hours, indicating their long-lasting effect.
Article
Chemistry, Multidisciplinary
Anna Kovalova, Vit Prouza, Martin Zavrel, Miroslav Hajek, Rastislav Dzijak, Alzbeta Magdolenova, Radek Pohl, Zdenek Voburka, Kamil Parkan, Milan Vrabel
Summary: This study presents a method for identifying lectin-binding ligands with low micromolar affinity by screening synthetic click glycopeptide libraries. The selected glycopeptides showed enhanced binding potency to the target lectins compared to the starting sugar moieties. This approach offers a promising alternative means of discovering ligands for galectins and other carbohydrate-binding proteins.
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)
