Article
Chemistry, Physical
Heyan Jiang, Cuicui Zang, Hongmei Cheng, Bin Sun, Xue Gao
Summary: Porous borocarbonitride (P-BCN) with enhanced crystallinity and improved N-B pair exposure was prepared using a simple KCl-assisted molten salt strategy, enabling efficient heterogeneous photocatalytic synthesis of benzazoles. The improved photocatalytic performance is attributed to the enhancement in charge separation and transmission, as well as the promotion of superoxide radical generation and oxidation ability. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicals through metal-free heterogeneous photocatalysis.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Organic
Shaofeng Wu, Furong Geng, Jianyu Dong, Long Liu, Yongbo Zhou
Summary: A metal-free and highly general synthesis of benzoxazoles from abundant phenols and amines has been developed using TEMPO-controlled phenol functionalization. This method offers advantages in terms of generality, selectivity, efficiency, and atom-and-step economies over traditional methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Sushil R. Mathapati, Komal N. Patil, Sujit S. Mathakari, Appasaheb W. Suryawanshi, Arvind H. Jadhav
Summary: This study describes the synthesis of a series of benzimidazoles, benzoxazoles, and benzothiazoles using 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol as starting materials and aryl, aliphatic and heteroaryl aldehydes as reactants. The use of 5 mol % fluorophosphoric acid as a catalyst in ethanol solvent at room temperature led to efficient synthesis with shorter reaction times, simple work-up techniques, high yields, and easy availability as key advantages of this approach.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2021)
Article
Chemistry, Multidisciplinary
Rakhi Katla, Ramesh Katla, Nelson Luis C. Domingues
Summary: In this study, a quick and eco-friendly method for synthesizing biologically active 2-substituted benzimidazoles and benzothiazoles was developed using Zn(L-Pro)(2) as a catalyst in ethanol at room temperature through an aerobic oxidative cyclization reaction involving o-phenylenediamine and 2-aminothiophenol with various substituted aldehydes.
Article
Chemistry, Organic
Mugada Sugunakara Rao, Sahid Hussain
Summary: This study presents a simple and efficient TEMPO-mediated system for the aerobic oxidative synthesis of 2-aryl benzoxazoles from readily available benzoxazoles and primary benzylic and hetero benzylic amines. The reactions proceed through ring-opening of benzoxazoles followed by oxidative condensation with benzylamines, yielding moderate to good yields with a variety of substrates under mild conditions using air as an external green oxidant.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hadi Kargar, Khadijeh Kargar, Mehdi Fallah-Mehrjardi, Khurram Shahzad Munawar
Summary: A new ONO-tridentate Schiff base ligand and its metal complexes exhibited excellent catalytic activities in the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles, showing high yields and environmentally friendly characteristics.
MONATSHEFTE FUR CHEMIE
(2021)
Article
Chemistry, Medicinal
Anja Bec, Livio Racane, Teo Tomic, Leentje Persoons, Dirk Daelemans, Mihailo Banjanac, Vedrana Radovanovic, Marijana Hranjec
Summary: The aim of this study was to synthesize novel benzazoles with amidino and 2-hydroxyphenyl substituents and explore their biological activity. New benzazoles were synthesized by condensation of 5-substituted salicylaldehydes and intermediates using previously developed procedures, and were tested for antibacterial and antiproliferative activity in vitro. The results showed that benzimidazole with a 2-imidazolinyl group 27 and benzothiazole with an unsubstituted amidine 48 exhibited the best antibacterial activity (minimum inhibitory concentration 8 μg/ml). Benzothiazole 53 was found to be the most potent compound in inhibiting the proliferation of various cancer cells (IC50: 1.2-2.0 μM). In conclusion, the most active compounds have been identified as lead compounds for further optimization to enhance their biological activity. The type of amidine moiety significantly influenced the biological activity, with benzothiazoles showing superior antiproliferative activity compared to benzimidazoles.
FUTURE MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Physical
Andrea Rogolino, Jose B. G. Filho, Lorena Fritsch, Jose D. Ardisson, Marcos A. R. da Silva, Gabriel Ali Atta Diab, Ingrid Fernandes Silva, Carlos Andree Ferreira Moraes, Moacir Rossi Forim, Matthias Bauer, Thomas D. Kuehne, Markus Antonietti, Ivo F. Teixeira
Summary: In this work, FeCl3 salt in acetonitrile was found to catalyze the oxidation of propane to acetone under aerobic conditions and visible-light irradiation at room temperature. Mechanistic studies showed that this reaction is driven by chlorine radicals generated by Fe-Cl bond photolysis. These findings not only have potential applications in the solar-based oxidation of hydrocarbons, but also provide important insights into the photochemistry of FeCl3.
Article
Biochemistry & Molecular Biology
Valentina Rep Kaulic, Livio Racane, Marijana Leventic, Domagoj Subaric, Vesna Rastija, Ljubica Glavas-Obrovac, Silvana Raic-Malic
Summary: Syntheses of 6-halogen-substituted benzothiazoles and 6-amidino-substituted benzothiazoles were performed. The antiproliferative activity of the compounds was evaluated on tumor cell lines, and it was found that the amidino benzothiazoles exhibited stronger inhibitory activity compared to non-substituted and halogen-substituted benzothiazoles. Imidazolyl benzothiazoles showed nonselective activity, except for 36c which had a strong inhibitory effect on HuT78 cells without cytotoxicity on normal cells. Structural analogs containing the 1,2,3-triazole ring showed pronounced and selective activity against HuT78 cells. QSAR models elucidated the effects of the substituents at position 6 of benzazoles on the antiproliferative activity.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Srimanta Manna, Wei-Jun Kong, Jan-E Backvall
Summary: This study presents an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions, inspired by oxidations in the respiratory chain. The method utilizes environmentally friendly and inexpensive catalysts, delivering important heterocycles in good-to-excellent yields with a broad substrate scope.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Livio Racane, Ivo Zlatar, Natasa Perin, Maja Cindric, Vedrana Radovanovic, Mihailo Banjanac, Suresh Shanmugam, Marijana Radic Stojkovic, Karmen Brajsa, Marijana Hranjec
Summary: Newly designed and synthesized compounds with benzimidazole/benzothiazole structures showed potential antitumor activity by inhibiting proliferation of human lung cancer cell lines. Benzothiazole derivatives exhibited higher activity compared to benzimidazole derivatives. Some compounds also demonstrated antimicrobial activity.
Article
Chemistry, Organic
Xinxin Qiao, Yong-De Zhao, Mingru Rao, Zhan-Wei Bu, Guangwu Zhang, Heng-Ying Xiong
Summary: An unexpected cleavage of the C-sp3-CF3 bond of CF3-hydrobenzoxazoles has been discovered, leading to the synthesis of a range of 2-aryl benzoxazoles under metal-free and redox-neutral conditions. The reaction demonstrates broad substrate scope and good compatibility of functional groups, offering an alternative, facile, and sustainable route to access important 2-aryl benzoxazole motifs.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Gabor Gyorke, Andras Dancso, Balazs Volk, David Hunyadi, Imre Szaloki, Anna Bulatko, Matyas Milen
Summary: Copper is abundant on Earth and copper catalysis in organic syntheses offers economical and environmentally friendly procedures. This study demonstrates the preparation of benzoxazoles and benzothiazoles from inexpensive starting materials in the presence of naturally occurring copper-containing minerals. The reaction was feasible with various minerals, resulting in good yields and high purity of the products.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Medicinal
Abigail C. Jackson, Tyler B. J. Pinter, Daniel C. Talley, Adnan Baker-Agha, Dhruvil Patel, Paul J. Smith, Katherine J. Franz
Summary: Metallo-beta-lactamases, such as NDM-1, utilize catalytic zinc ions in their active sites and have the ability to hydrolyze nearly all clinically available beta-lactam antibiotics. Inhibitors of metallo-beta-lactamases, which are urgently needed to combat antibacterial drug resistance, show promise in zinc-binding compounds. Evaluating 13 chelating agents containing benzimidazole and benzoxazole scaffolds as NDM-1 inhibitors revealed six compounds with potent inhibitory activity, suggesting potential for further development as NDM-1 inhibitors.
Article
Chemistry, Multidisciplinary
Qi Zhao, Yongtao Wang, Yu Wang, Qixuan Hu, Jia Yao, Zeyu Wen, Haoran Li
Summary: The main product from keto acid to alpha-hydroxyl ketone can be effectively controlled by reducing the concentration of FeCl3 catalyst and using DMSO as the solvent. Mechanistic investigations indicate that the same FeCl3-coordinated peroxide intermediate plays a role in both hydroxylation and C-C cleavage routes, and emphasize the role of DMSO as both ligand and reductant. This work provides a new approach for selective aerobic oxidation under Lewis acid catalysis.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Dilek Isik Tasgin, Irem Bayraktar
Summary: We present a synthetic method for pyrrolizine-3-one derivatives and investigate their photophysical properties. These compounds are prepared through a series of reactions involving substituted pyrroles in one-pot, two-step oxidation, and intramolecular cyclization processes. The photophysical properties of the synthesized compounds are studied using UV-Vis and fluorescence spectroscopy in various solvents. The introduction of pyrrolyl substituents has a significant impact on Stokes shifts and quantum yield values.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Satish Kumar Burra, Vaikunta Rao Lakinani, Raghunadh Akula, Chiranjeevi Yankkanti
Summary: A novel and green strategy for the construction of biologically relevant substituted indolyl-4H-chromenes scaffolds is reported, using L-proline as a catalyst and water as a promoter solvent. This catalytic system offers wider applicability, shorter reaction times, and high yields, making it an ideal condition for green chemistry.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Abouelhaoul El Alami, Amine El Maraghi, Fatima Youssoufi, Assiya Atif, Hamid Sdassi
Summary: Nitrobenzimidazoles have become increasingly important in the design of new compounds in medicinal, therapeutic and chemical fields. This review provides an overview of the synthesis strategies and biological activities of nitrobenzimidazole derivatives.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Nilesh Raghunath Khedkar, Alex Joseph, Milind Sindkhedkar
Summary: In this study, a new library of 3-(2-(pyrimidin-5-yl)thiazol-4-yl)-1,2,4-oxadiazole compounds was designed and synthesized as potential anticancer agents using in silico fragment-based drug design. The compounds were tested for their anticancer activity in vitro, and one compound exhibited excellent activity against multiple cancer cell lines.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Terungwa H. Iorkula, Bryce A. Tolman, Scott R. Burt, Matt A. Peterson
Summary: A new method for synthesizing C-6 substituted products has been discovered in this study, which utilizes lower doses of fluoride and CsF as a catalyst, with high reaction yields and cost-effectiveness under suitable conditions.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Ranjana Aggarwal, Swati Sharma
Summary: This review article mainly focuses on the synthesis of 3(5)-trifluoromethylpyrazoles via condensation reaction of trifluoromethyl-beta-diketones with hydrazines. It emphasizes the importance of fluorine-containing compounds and pyrazoles in the field of biology. The literature reported condensation reactions of trifluoromethyl-beta-diketones with hydrazines are covered.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
F. M. Alshareef, Sami A. Al-Harbi, Esam S. Allehyani, Omeima Abdullah, Magdy A. Ibrahim
Summary: This study aimed to construct a novel category of linear annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3]thiazolo[3,2-a]pyrimidines. The chemical reactivity of the synthesized compounds was investigated, and they showed significant antimicrobial activity against various strains.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Preethi Dhanapal, S. L. Manju
Summary: Thiazole based Schiff base scaffolds have become an integral part of drug development in recent years, playing a versatile role as building blocks for lead drug molecules. This study presents a facile one pot synthetic method for producing novel 4-aryl thiazoles with high yield, shorter reaction time, and milder conditions, without the need for catalysts or purification techniques.
SYNTHETIC COMMUNICATIONS
(2024)