Abstract: The synthesis and characterization of Nickel(II) complexes with novel pincer-type N-heterocyclic carbene complexes were investigated. Nickel(II)-NHC complexes, 7 and 8, were characterized using HR ESI-MS, IR, UV-Visible, and elemental analysis. The complex 7 with less sterically demanding pincer ligand was investigated in the catalytic one pot synthesis of thioethers via coupling reactions of a series of aryl and alkyl halides in the presence of thiourea. In a mixture of water and ethanol, 5 mol% of 7 catalyzed the C-S bond coupling reaction in high yields.
Anticancer Properties of Ru and Os Half‐Sandwich Complexes of N,S Bidentate Schiff Base Ligands Derived from Phenylthiocarbamide
The versatile coordinating nature of N,S bidentate ligands is of great importance in medicinal chemistry imparting stability and enhancing biological properties of the metal complexes. Phenylthiocarbamide-based N,S donor Schiff bases converted into RuII/OsII(cymene) complexes and characterized by spectroscopic techniques and elemental analysis. The hydrolytic stability of metal complexes to undergo metal-halido ligand exchange reaction was confirmed both by the DFT and NMR experimentation. The ONIOM (QM/MM) study confirmed the histone protein targeting nature of aqua/hydroxido complex 2aH with an excellent binding energy of -103.19 kcal/mol. The antiproliferative activity against a panel of cancer cells A549, MCF-7, PC-3, and HepG2 revealed that ruthenium complexes 1a–3a were more cytotoxic than osmium complexes and their respective ligands 1–3 as well. Among these ruthenium cymene complex bearing sulfonamide moiety 2a proved a strong cytotoxic agent and showed excellent correlation of cellular accumulation, lipophilicity, and drug-likeness to the anticancer activity. Moreover, the favorable physiochemical properties such as bioavailability and gastrointestinal absorption of ligand 2 also supported the development of Ru complex 2a as an orally active anticancer metallodrug.
Metallaphotoredox‐catalyzed three‐component couplings for the practical synthesis of ureas and carbamates
Comprehensive Summary
Ureas are widely used in drugs, materials and catalysts because of their diamide structure, which can form strong hydrogen bonds. Therefore, it is of great scientific significance to develop efficient and green methods for the synthesis of urea compounds, especially unsymmetrical ureas. Here, we have disclosed novel and highly efficient three-component coupling reactions of organic halides, sodium cyanate and amines enabled by nickel/photoredox dual catalysis for the preparation of unsymmetrical ureas. The reaction features simple and safe operations, broad substrate scopes, and product diversities. It allows the facile synthesis of N-aryl/vinyl ureas from readily available, user-friendly feedstocks under mild conditions (27 examples, 36-98% yields). In addition, this method is further derived to alcohols as nucleophiles to synthesize a series of carbamates (15 examples, 40-95% yields). The mechanism experiment shows that the isocyanate produced by the coupling of halide and sodium cyanate may be the key intermediate in this reaction.
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Synthesis, crystal structures and antimicrobial activities of 3-methyl and 3-bromo substituted benzo[b]thiophene based thiosemicarbazones
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Unraveling the Interactions between Nanoparticles and Benzo[a]pyrene in Environmental Waters and Human Blood by Dissipative Particle Dynamics Simulations
Chemistry Letters, Ahead of Print.
Pin-point surgery of proton-deuterium substitution to enhance polybenzimidazole thermoresistances
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Influence of doped elements (O, K, and N) on melamine derived g-C3N4: insights into optical properties and photoactivity
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A novel cyclobutane-derived thiazole–thiourea hybrid with a potency against COVID-19 and tick-borne encephalitis: synthesis, characterization, and computational analysis
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[ASAP] A Multichannel Fluorescence Isothermal Amplification Device with Integrated Internet of Medical Things for Rapid Sensing of Pathogens through Deep Learning
Analytical Chemistry
DOI: 10.1021/acs.analchem.3c02973
Antimalarial Agents Targeting Plasmodium falciparum Carbonic Anhydrase: Towards Artesunate Hybrid Compounds with Dual Mechanism of Action
The development of new artesunate hybrid compounds containing benzenesulfonamide chemotypes as antimalarial agents through a dual mechanism of action: fast-acting ROS generation and long-lasting Plasmodium falciparum carbonic anhydrase (PfCA) inhibition.
Abstract
Malaria continues to be a major public health challenge worldwide and, as part of the global effort toward malaria eradication, plasmodium carbonic anhydrases (CAs) have recently been proposed as potential targets for malaria treatment. In this study, a series of eight hybrid compounds combining the Artesunate core with a sulfonamide moiety were synthesized and evaluated for their inhibition potency against the widely expressed human (h) CAs I, II and the isoform from P. falciparum (PfCA). All derivatives demonstrated high inhibition potency against PfCA, achieving a KI value in the sub-nanomolar range (0.35 nM). Two Compounds showed a selectivity index of 4.1 and 3.1, respectively, against this protozoan isoform compared to hCA II. Three Derivatives showed no cytotoxic effects on human gingival fibroblasts at 50 μM with a high killing rate against both P. falciparum and P. knowlesi strains with IC50 in the sub-nanomolar range, providing a wide therapeutic window. Our findings suggest that these compounds may serve as promising leads for developing new antimalarial drugs and warrant further investigation, including activity against antimalarial-resistant strains, mode of action studies, and in vivo efficacy assessment in preclinical mouse models of malaria.