Article
Chemistry, Organic
Yuxin Ding, Jinqiang Kuang, Xuqiong Xiao, Lei Wang, Yongmin Ma
Summary: An efficient iron-catalyzed cross-dehydrogenative coupling [4 + 2] annulation of secondary/tertiary anilines with quinazolinones to generate quinoline-spiroquinzolinones was reported. The reaction proceeds smoothly with a relatively broad variety of functional groups, a cheap transition metal catalyst (FeCl3), and environmentally friendly oxidant (H2O2/O2) under mild reaction conditions. Additionally, N-methylanilines were creatively employed for the first time as both methyl and methylene sources attached to the N atom of tetrahydroquinolines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Saghir Ali, Abu T. Khan
Summary: The novel and expedient metal- and solvent-free synthesis method described in this study utilizes readily available starting materials to form 2-benzyl-4-arylquinoline derivatives under mild conditions, with high regioselectivity and a wide tolerance for functional groups. This efficient and environmentally friendly approach involves the formation of one C-N and two C-C bonds, avoiding the need for metal catalysts and minimizing waste generation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Aayushi Lodhi, Kalpana C. Maheria
Summary: Quinazolinones are important nitrogen-containing heterocyclic compounds with diverse biological activities. The synthesis of quinazolinone faces challenges such as multistep synthesis and the use of hazardous chemicals, but catalysis offers a solution. This review summarizes sustainable synthesis strategies and the use of solid acid catalysts for quinazolinone-based molecules.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2023)
Article
Chemistry, Organic
Xinchang Li, Huiru Yang, Zheyao Hu, Xin Jin, Wenyi Zhang, Xunxiang Guo
Summary: An environmentally benign protocol of visible-light-induced reaction has been developed for the effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides. The reaction proceeds well under metal-free, photocatalyst-free and mediator-free conditions, providing the corresponding quinazolinones in good to high yields. Mechanism studies suggest that a radical pathway might be involved in the reaction.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Harrison M. Snodgrass, Dibyendu Mondal, Jared C. Lewis
Summary: In this study, a variant of the flavin-dependent halogenase RebH was engineered to catalyze site- and atroposelective halogenation reactions of 3-aryl-4(3H)-quinazolinones. The directed evolution process used a combination of mutagenesis, substrate walking, and screening methods to improve the conversion and selectivity of the enzyme. The resulting variant showed high activity and selectivity on multiple substrates, and computational modeling was used to understand the effects of key mutations on substrate binding. This study demonstrates the potential of flavin-dependent halogenases for atroposelective catalysis and highlights the versatility of RebH in accepting structurally diverse substrates for enantioselective synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Tatyana N. Moshkina, Emiliya Nosova, Julia Permyakova, Galina N. Lipunova, Ekaterina F. Zhilina, Grigory A. Kim, Pavel A. Slepukhin, Valery N. Charushin
Summary: This study describes the design and synthesis of compounds with Et2N, Ph2N, or carbazole-9-yl electron donating fragments, and investigates their photophysical properties. The influence of different donor fragments on fluorescence quantum yields and emission intensity is demonstrated. Some compounds show enhanced fluorescence intensity in response to the addition of water in solution.
Article
Chemistry, Applied
Alexander K. Eltyshev, Timur H. Dzhumaniyazov, Polina O. Suntsova, Artem S. Minin, Varvara A. Pozdina, Wim Dehaen, Enrico Benassi, Nataliya P. Belskaya
Summary: New fluorescent thiazoles were synthesized with specific combinations of substituents, resulting in a wide range of fluorescent colors and intensities. Further research revealed that certain substituent combinations could increase emission rates. These thiazoles displayed multifunctional properties, showing good emission in solid and suspension states, as well as a tunable response in different solvents.
Article
Chemistry, Multidisciplinary
N. A. Pakholka, V. L. Abramenko, V. V. Dotsenko, N. A. Aksenov, I. Aksenova, S. G. Krivokolysko
Summary: Bromination of (2E)-3-aryl(hetaryl)-2-[4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles proceeds regioselectively at the C-5 atom of the thiazole ring with the formation of new (2E)-3-aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles. The latter were alternatively obtained by the reaction of aldehydes, cyanothioacetamide, alpha-bromoketones and bromine in the presence of triethylamine in DMF. Structure of the key compounds was confirmed using 2D NMR spectroscopy and single crystal X-ray diffraction analysis.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Weiqiang Chen, Mei Liu, Hui-Jing Li, Yan-Chao Wu
Summary: Switchable chemoselective conversion of 2-amido-aryl oxazolines to quinazolin-4(3H)-ones or N-(2-chloroethyl)benzamides is achieved. The reactions proceed smoothly under mild conditions and have excellent functional group compatibility, offering a practical and efficient method for selective transformations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Indira Meeniga, Anusha Gokanapalli, Vasu Govardhana Reddy Peddiahgari
Summary: Ionic liquids have a significant impact on academic and industrial applications due to their potential in sustainable research. The synthesis of ILs with various counter-anions can be applied in organic catalysis, and utilizing ultrasonication in reactions can lead to improved outcomes.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2022)
Review
Chemistry, Medicinal
Fabiana Plescia, Benedetta Maggio, Giuseppe Daidone, Demetrio Raffa
Summary: The quinazolinone nucleus is an important scaffold for obtaining biologically active molecules. Fused heterocycles from natural or synthetic sources are associated with a wide range of biological activities. This review focuses on 4-(3H)-quinazolinones N-3 substituted with a five-membered heterocycle containing nitrogen, sulfur, and oxygen atoms in various combinations.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Nayoung Ko, Sujin Min, Kyeongwon Moon, Hyungjin Shin, Na Yeon Kwon, Neeraj Kumar Mishra, Amitava Rakshit, Pargat Singh, In Su Kim
Summary: This study presents a method for site-selective modification of quinazolinone, a privileged bicyclic N-heterocycle that is of great interest in medicinal chemistry and material science. A ruthenium(II)-catalyzed C-H allylation of 2-aryl quinazolinones with 2-methylidene cyclic carbonate was demonstrated, and tandem C-H allylation and annulation under rhodium(III) catalysis were achieved, leading to the formation of tetracyclic quinazolinones with a tertiary carbon center. The potential of the developed methodology was further demonstrated through post-transformations of the synthesized products, and mechanistic investigations were also conducted.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shaodong Kang, Jiaxing Li, Qin Yang, Zhibin Song, Yiyuan Peng
Summary: An efficient method for accessing 2-(2-beta-aryl ketone) substituted 2-arylquinazolinones has been described. 2-Carboxyl allylic alcohols derived from Morita-Baylis-Hillman adducts were used as the building blocks. The reaction between 2-aryl quinazolinones and 3-hydroxy-2-methylene-5-phenylpentanoic acid, catalyzed by [RhCp*Cl-2](2)-CF3COOAg, underwent C-H activation and decarboxylation to provide the desired products in good to excellent yields. Control experiments suggested that the nitrogen atom at the 3-position of the quinazolinone scaffold might serve as the directing group in this C-H activation/functionalization. A plausible mechanistic pathway for the synthesis of the target compounds is proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Abdolrahman Keyhani, Mohammad Nikpassand, Leila Zare Fekri, Hassan Kefayati
Summary: Tannic acid-functionalized silica-coated Fe3O4 nanoparticles were used to synthesize 2-aryl-quinazolinones in an eco-friendly manner, resulting in high yields and short reaction times. The catalyst showed good recyclability and the structures of the compounds were confirmed through various spectroscopic techniques.
JOURNAL OF CLUSTER SCIENCE
(2022)
Article
Chemistry, Organic
Li Pang, Shu-Jun Fang, Pei-Sen Zou, Wang Wang, Jun-Cheng Su, Xiao-Qing Liu, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
Summary: We report a transition-metal free [4 + 4] cycloaddition reaction between 2-alkynyl quinazolines and aza-ortho-quinone methides (ao-QMs) generated from 2-(bromomethyl)anilines, leading to the synthesis of various [1,5]diazocino[2,1-b]quinazolinones in good to excellent yields under mild reaction conditions and short reaction time. Furthermore, a [1,5]diazocino[2,1-b]quinazolinone derived from estrone was easily prepared in 30% total yield over five steps, and showed significant inhibition of nitric oxide generation in LPS-stimulated RAW264.7 cells. This method offers advantages such as broad substrate scope, gram-scale preparation, and simple purification operation without flash column chromatography.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Kateryna Vus, Mykhailo Girych, Valeriya Trusova, Galyna Gorbenko, Atanas Kurutos, Aleksey Vasilev, Nikolai Gadjev, Todor Deligeorgiev
JOURNAL OF MOLECULAR LIQUIDS
(2019)
Article
Chemistry, Organic
Meglena I. Kandinska, Snejana M. Kitova, Vladimira S. Videva, Stanimir S. Stoyanov, Stanislava B. Yordanova, Stanislav B. Baluschev, Silvia E. Angelova, Aleksey A. Vasilev
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Physical
Atanas Kurutos, Tatjana Ilic-Tomic, Fadhil S. Kamounah, Aleksey A. Vasilev, Jasmina Nikodinovic-Runic
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
(2020)
Article
Chemistry, Applied
Olga Zhytniakivska, Mykhailo Girych, Valeriya Trusova, Galyna Gorbenko, Aleksey Vasilev, Meglena Kandinska, Atanas Kurutos, Stanislav B. Baluschev
Article
Chemistry, Multidisciplinary
Ines F. A Mariz, Sandra N. Pinto, Ana M. Santiago, Jose M. G Martinho, Javier Recio, Juan J. Vaquero, Ana M. Cuadro, Ermelinda Macoas
Summary: The study demonstrates the potential of quinolizinium and benzimidazolium cations for targeted mitochondrial damage through two-photon absorption in the near infrared range. These compounds can efficiently disrupt mitochondrial potential and induce cell death under two-photon excitation, suggesting possible applications as precision photosensitizers. The interaction with mitochondria leads to an unexpected blue-shift of the emission of the far-red emitting compounds, indicating potential limitations in accessing the intramolecular charge transfer state for far-red emission due to interaction and aggregation at mitochondria.
COMMUNICATIONS CHEMISTRY
(2021)
Article
Chemistry, Applied
Agnieszka Mierczynska-Vasilev, Aleksey Vasilev, Tim Reilly, Keren Bindon, Krasimir Vasilev
Summary: A fast and efficient fluorescence-based method for detecting haze-forming proteins in white wine is developed, showing linear dependence and low detection limit.
Article
Chemistry, Multidisciplinary
Aleksey Vasilev, Anton Kostadinov, Meglena Kandinska, Katharina Landfester, Stanislav Baluschev
Summary: Optically excited triplet states of organic molecules serve as an energy pool for subsequent processes, which is essential for optoelectronic applications.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Aleksey A. Vasilev, Marina Miteva, Nikolay Ishkitiev, Maria Dragneva, Lora Topalova, Meglena I. Kandinska
Summary: In this study, a new compound was synthesized by a convenient and reliable method, and its fluorescence properties in DNA were investigated. The compound showed no toxicity to stem cells from apical papilla and exhibited concentrated fluorescence in the cell nucleoli.
Article
Chemistry, Organic
Aleksey A. Vasilev, Peter P. Grozdanov, Ivanka Nikolova, Valentin S. Lozanov, Meglena Kandinska
Summary: The quinoline scaffold is a widely used pharmacophore in drug design, and this study presents an environmentally tolerant synthetic approach for novel chloroquine and hydroxychloroquine analogues.
Article
Biochemistry & Molecular Biology
Iva Zonjic, Marijana Radic Stojkovic, Ivo Crnolatac, Ana Tomasic Paic, Silvia Psenicnik, Aleksey Vasilev, Meglena Kandinska, Mihail Mondeshki, Stanislav Baluschev, Katharina Landfester, Ljubica Glavas-Obrovac, Marijana Jukic, Juran Kralj, Anamaria Brozovic, Lucija Horvat, Lidija-Marija Tumir
Summary: New monomethine, unsymmetrical styryl dyes consisting of benzothiazole and N-methylpiperazine or N-phenylpiperazine scaffolds were synthesized and studied for their binding affinities for different ds-polynucleotides and G-quadruplex. The substitution of piperazine unit strongly influenced their binding modes, affinities, spectroscopic responses, and antiproliferative activities. N-methylpiperazine-substituted compounds showed a preference for AT-DNA polynucleotides and demonstrated AT-minor groove binding, while N-phenylpiperazine substituted compounds showed stronger stabilization of G-quadruplex. Fluorimetric titrations suggested possible mixed stoichiometries with G-quadruplex. Compounds with N-phenylpiperazine fragments exhibited micromolar and submicromolar antiproliferative activity, particularly against leukemia and lymphoma.
BIOORGANIC CHEMISTRY
(2022)
Article
Nutrition & Dietetics
Laura Martinez-Arias, Sara Fernandez-Villabrille, Cristina Alonso-Montes, Gonzalo Garcia-Navazo, Maria P. Ruiz-Torres, Ramon Alajarin, Julio Alvarez-Builla, Elena Gutierrez-Calabres, Juan Jose Vaquero-Lopez, Natalia Carrillo-Lopez, Diego Rodriguez-Puyol, Jorge B. Cannata-Andia, Sara Panizo, Manuel Naves-Diaz
Summary: This study examined the effects of GGN1231, a hybrid compound derived from losartan, in a rat model of chronic renal failure. The results showed that GGN1231 reduced cardiovascular damage and fibrosis, suggesting its potential in managing cardiovascular and inflammatory processes.
Article
Chemistry, Organic
Aleksey A. Vasilev, Meglena I. Kandinska, Anton Kostadinov, Laura Dietz, Stanislav Baluschev
Summary: The development of new selective fluorogenic probes for monitoring microbiological objects and cellular compartments is crucial for understanding the mechanism of pathogenesis of new pathogens in living cells. In this study, a reliable synthetic strategy was presented to prepare a chemically pure dye, and its photophysical properties and cellular uptake were investigated.
Article
Chemistry, Multidisciplinary
Javier Recio, Fabiana Filace, Elena Gala, Adrian Perez-Redondo, Julio Alvarez-Builla, Carolina Burgos
Article
Chemistry, Organic
Javier Recio, Adrian Perez-Redondo, Julio Alvarez-Builla, Carolina Burgos
ORGANIC CHEMISTRY FRONTIERS
(2019)
Article
Electrochemistry
A. Popova, A. Vasilev, T. Deligeorgiev
PORTUGALIAE ELECTROCHIMICA ACTA
(2018)
