Article
Biochemistry & Molecular Biology
Jehan Y. Al-Humaidi, Siham A. Alissa, Kanubhai D. Katariya, Khulood A. Abu Al-Ola, Mohamed Hagar, Khaled D. Khalil
Summary: A series of high temperature alkyl and alkoxy biphenyltetracarboxydiimide liquid crystals were prepared under a ball mill method in a solvent-free mechanochemical approach. The thermal properties and textures of the compounds were investigated, showing smectic mesomorphic behavior. DFT theoretical calculations revealed the impact of terminal chain polarity on the molecular structure and properties of the prepared compounds.
Article
Chemistry, Multidisciplinary
Sevinc Ilkar Erdagi, Ufuk Yildiz
Summary: This study focuses on the synthesis of spirostan derivatives as potential drug candidates, which possess anti-cancer, anti-diabetes, and anti-inflammatory properties. Through the design and synthesis of nitrogen-containing novel spirostan derivatives, their chemical structures were characterized. The results showed that these derivatives exhibited potent anticancer activity in human cancer cells and were non-toxic to human cells.
Article
Biochemistry & Molecular Biology
Jose Clerigue, M. Teresa Ramos, J. Carlos Menendez
Summary: Mechanochemical conditions were utilized for the aza-vinylogous Povarov reaction, resulting in faster reactions with comparable yields to conventional methods. The reaction yielded 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-1,5-naphthyridines functionalized at C-2, C-4 and C-6 positions.
Article
Chemistry, Organic
Marco Thomas Passia, Jan-Hendrik Schoebel, Niklas Julian Lentelink, Khai-Nghi Truong, Kari Rissanen, Carsten Bolm
Summary: In this study, TBS-protected or NH-sulfonimidamides were reacted with beta-alkoxyvinyl trifluoromethylketones under solvent-free mechanochemical conditions to produce 3-trifluoromethyl-substituted three-dimensional 1,2,6-thiadiazine 1-oxides. C4-functionalized products were obtained by starting from cyclic enones and brominations of the initially formed heterocycles. The stability of the products was investigated by varying the pH value and storage under aerobic conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The method involves the aminocatalytic activation of 2-alkyl-3-furfurals and proceeds via the formation of dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates. The mechanism of the transformation was confirmed through DFT calculations.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mateusz Dyguda, Artur Przydacz, Lukasz Albrecht
Summary: This manuscript describes the application of dearomative formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines. The developed approach utilizes aminocatalytic activation of 2-alkyl-3-furfurals that proceeds via formation of the dearomatized dienamine intermediate. The obtained cycloadducts can be further transformed into tetrahydrofuropyridines or functionalized cinnamates.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Camila R. S. Bertallo, Leonardo S. Berlim, Danilo S. Olivier, Thais R. Arroio, Amando S. Ito, Giuliano C. Clososki
Summary: In this study, 20 novel fluorescent 5-carbonylated 2-arylindolizines derivatives were synthesized through the reaction between organolithium intermediates with different electrophiles. The photophysical properties, including electronic absorption spectra, fluorescence emission, quantum yield, and Stokes shift, were evaluated to investigate the effects of substituents. The results showed variations in absorbance peaks, fluorescence emission, decay times, quantum yield values, and Stokes shifts, with DFT calculations also performed for further analysis.
Article
Biochemistry & Molecular Biology
Hugo Rojas-Chavez, Alan Miralrio, Jose M. Juarez-Garcia, Guillermo Carbajal-Franco, Heriberto Cruz-Martinez, Fernando Montejo-Alvaro, Manuel A. Valdes-Madrigal
Summary: The study evaluated the effectiveness of TBP as a surface modifier of PbTe, using density functional theory to calculate global and local descriptors, and comparing the behavior of TBP and CH2O molecules on the PbTe surface. The insights from the theoretical calculations were found to be crucial for understanding the adsorption modes of TBP and CH2O on the PbTe surface and rationalizing the facets displayed.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Andrea Porcheddu, Rita Mocci, Margherita Brindisi, Federico Cuccu, Claudia Fattuoni, Francesco Delogu, Evelina Colacino, Maria Valeria D'Auria
Summary: An environmentally friendly mechanochemical protocol was developed to synthesize indoles and indolines using oxalic acid and dimethylurea. The solvent-free procedure showed versatility and wide scope, leading to variously decorated compounds. The methodology also has potential for preparing compounds of pharmaceutical interest.
Article
Chemistry, Multidisciplinary
Arne Heusler, Julian Fliege, Tobias Wagener, Frank Glorius
Summary: A novel method for the synthesis of a broad variety of N-substituted 1,4- and 1,2-dihydropyridines using amine borane as a mild and selective reducing agent is reported, expanding the scope of dearomatization strategies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Svetlana A. Kondrashova, Shamil K. Latypov
Summary: The study examines the scopes and limitations of theoretical methods for estimating various NMR metrics of NHCs using computational approximations on a range of model NHCs and their derivatives. It concludes that the most reliable methods are the 31P/13C NMR shifts of NHC-phosphinidene adducts and 13C CSs of carbenes, while the method based on the analysis of 77Se CS NHC-selenoureas has some limitations due to exchange effects. The accuracy of estimating the HEP metric may also be limited due to the nonlinear effect of electron distribution. 13C CSs of NHC-azolium salts are deemed unreliable due to the influence of counterion exchange.
Article
Chemistry, Applied
Siqi Zhu, Fang Li, Claire Empel, Sripati Jana, Chao Pei, Rene M. Koenigs
Summary: Here, we report a photocatalytic reaction of acceptor/acceptor diazoalkanes with terminal alkynes, leading to the formation of furan heterocycles. Experimental and computational studies reveal the involvement of a key triplet carbene intermediate, which undergoes addition reaction followed by cyclization. This reaction provides a mild and efficient method for the synthesis of furans using a broad range of substrates.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Byeongseok Kweon, Changha Kim, Seonyul Kim, Sungwoo Hong
Summary: An efficient strategy for remote C-H pyridylation of hydroxamates with excellent ortho-selectivity has been developed by designing new photon-absorbing O-aryl oxime pyridinium salts. The photoexcitation of oxime pyridinium intermediates generates iminyl radicals via photolytic N-O bond cleavage, allowing for the installation of pyridyl rings at the gamma-CN position. This novel synthetic approach offers advantages in terms of efficiency, simplicity, and broad functional group tolerance under mild and metal-free conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Leman Alkan, Ozgur Alver, Stephen T. Astley, Eralp Kulan, Cemal Parlak
Summary: The tandem Knoevenagel-Michael addition of diethyl malonate to nitro-substituted benzaldehydes was found to proceed in a mild and convenient process. The H-1 NMR spectra of the products showed significant changes according to the position of the nitro group. Conformational analysis calculations confirmed the presence of a structure containing a mirror plane near the ground state in all cases. However, increased steric crowding in the meta and ortho substituted products resulted in decreased rotational freedom of the ethyl substituents. Molecular orbital calculations predicted a higher electrophilic reactivity of the ortho nitro substituted product, consistent with the observed increase in steric stress.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Shuai Jiang, Wen-Bin Cao, Xiao-Ping Xu, Shun-Jun Ji
Summary: A Co-catalyzed cyclization reaction of isocyanides, azides, and amines was developed to access quinazoline derivatives, featuring high atom economy, mild reaction conditions, excellent yields, and a broad substrate scope. The cascade reaction involved the formation of three to four C-N bonds and one or two rings, producing versatile intermediates for further transformations. The cobalt catalyst used in the reaction was found to be isolatable and reusable.
Article
Automation & Control Systems
Ozren Jovic, Katarina Piculjan, Tomica Hrenar, Tomislav Smolic, Ines Primozic
CHEMOMETRICS AND INTELLIGENT LABORATORY SYSTEMS
(2019)
Article
Chemistry, Medicinal
Linda Bazina, Ana Maravic, Lucija Krce, Barbara Soldo, Renata Odzak, Viljemka Butevic Popovic, Ivica Aviani, Ines Primozic, Matilda Sprung
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2019)
Article
Toxicology
Antonio Zandona, Maja Katalinic, Goran Sinko, Andreja Radman Kastelic, Ines Primozic, Zrinka Kovarik
ARCHIVES OF TOXICOLOGY
(2020)
Article
Pharmacology & Pharmacy
Ana Matosevic, Andreja Radman Kastelic, Ana Mikelic, Antonio Zandona, Maja Katalinic, Ines Primozic, Anita Bosak, Tomica Hrenar
Summary: The study confirmed that quinuclidinium carbamates are promising candidates for further development as CNS-active drugs, particularly for Alzheimer's disease treatment. The synthesized compounds showed good acetylcholinesterase and butyrylcholinesterase inhibitory activity, and were able to pass the blood-brain barrier.
Article
Biochemistry & Molecular Biology
Doris Crncevic, Lucija Krce, Linda Mastelic, Ana Maravic, Barbara Soldo, Ivica Aviani, Ines Primozic, Renata Odzak, Matilda Sprung
Summary: Quaternary ammonium compounds (QACs) are antimicrobial agents with broad spectrum activity targeting bacterial membrane. In this study, QACs based on imidazole derivative N-benzylimidazole showed potent antimicrobial activity against pathogenic bacteria, especially against bacterial biofilms. The most promising compound, N-tetradecyl derivative (BnI-14), demonstrated low toxicity to healthy human cells, suggesting potential as a new antimicrobial agent.
BIOORGANIC CHEMISTRY
(2021)
Article
Infectious Diseases
Alma Ramic, Mirjana Skocibusic, Renata Odzak, Ana Cipak Gasparovic, Lidija Milkovic, Ana Mikelic, Karlo Sovic, Ines Primozic, Tomica Hrenar
Summary: A series of N-substituted quaternary salts of cinchonidine were prepared and evaluated for their antimicrobial activity, showing good potential against a diverse panel of bacteria. By establishing an activity/potential energy surface model, accurate predictions of activity for new compounds can be made based solely on their potential energy surfaces, facilitating the search for new potential antibiotics.
Article
Energy & Fuels
Dubravka Raljevic, Jelena Parlov Vukovic, Vilko Smrecki, Ljiljana Marinic Pajc, Predrag Novak, Tomica Hrenar, Tomislav Jednacak, Lucija Konjevic, Bruno Pinevic, Tonka Gasparac
Summary: This study utilized statistical multi-way analysis and machine learning methods combined with diffusion-ordered NMR spectroscopy to explore the potential of predicting crude oil stability. By applying MWA and ML techniques, a robust model was developed to accurately predict crude oil stability and other important parameters, demonstrating great potential for practical applications in the petroleum industry.
Article
Biochemistry & Molecular Biology
Zlatan Spahi, Tomica Hrenar, Ines Primozi
Summary: In this study, four O-substituted oximes of quinuclidin-3-one were synthesized using appropriate O-substituted hydroxylamine hydrochlorides. Pure (E) oximes were obtained through mechanochemical and microwave synthesis. The reactions were monitored and analyzed using ATR spectroscopy and H-1 NMR data. The conformational analysis of reaction intermediates provided insights into the reaction mechanism. The study highlights alternatives to the classical synthesis of O-substituted oxime ether precursors, as well as the fast reaction rate and stereoselectivity of microwave synthesis and the environmentally friendly nature of mechanochemistry.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Visnja Vrdoljak, Tomica Hrenar, Mirta Rubcic, Gordana Pavlovic, Tomislav Friganovic, Marina Cindric
Summary: This study investigated the propensity of 4-hydroxybenzhydrazone-related ligands derived from 3-methoxysalicylaldehyde, 4-methoxysalicylaldehyde, and salicylaldehyde to act as chelating and/or bridging ligands in Ni(II) complexes. Different clusters with various nuclearities were prepared and characterized. The ligands in these clusters acted as singly or doubly deprotonated ligands. The stability and substituent effects of square-planar complexes were studied and quantified. The crystal and molecular structures of several complexes were determined.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Nikol Bebic, Edi Topic, Mirna Mandaric, Tomica Hrenar, Visnja Vrdoljak
Summary: Five hexamolybdate and five octamolybdate-based organic-inorganic hybrid assemblies were synthesized and characterized using X-ray crystallography, IR-ATR, and TG analysis. The study investigated the effects of reaction conditions and the coordination nature of Mo(VI) complex cations on the structure of the hybrid compounds, as well as the impact of different metal-organic components and solvents on the formation of the hybrids.
Article
Chemistry, Multidisciplinary
Jana Pisk, Ivica Dilovic, Tomica Hrenar, Danijela Cvijanovic, Gordana Pavlovic, Visnja Vrdoljak
Article
Chemistry, Multidisciplinary
Tomislav Jednacak, Maja Majeric Elenkov, Tomica Hrenar, Karlo Sovic, Jelena Parlov Vukovic, Predrag Novak
NEW JOURNAL OF CHEMISTRY
(2020)
