Synthesis of (E)-2-(1H-tetrazole-5-yl)-3-phenylacrylenenitrile derivatives catalyzed by new ZnO nanoparticles embedded in a thermally stable magnetic periodic mesoporous organosilica under green conditions

Scientific Reports, Journal Year: 2022, Volume and Issue: 12(1)

Published: June 24, 2022

Abstract ZnO nanoparticles embedded in a magnetic isocyanurate-based periodic mesoporous organosilica (Fe 3 O 4 @PMO–ICS–ZnO) were prepared through modified environmentally-benign procedure for the first time and properly characterized by appropriate spectroscopic analytical methods or techniques used materials. The new thermally stable Fe @PMO–ICS–ZnO nanomaterial with proper active sites surface area as well uniform particle size was investigated synthesis of medicinally important tetrazole derivatives cascade condensation concerted 1,3-cycloaddition reactions representative Click Chemistry concept. desired 5-substituted-1 H -tetrazole smoothly high to quantitative yields good purity EtOH under reflux conditions. Low catalyst loading, short reaction use green solvents such water instead carcinogenic DMF easy separation recyclability at least five consecutive runs without significant loss its activity are notable advantages this protocol compared other recent introduced procedures.

Language: Английский

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A new series of hydrazones as small‐molecule aldose reductase inhibitors

Archiv der Pharmazie, Journal Year: 2023, Volume and Issue: 356(4)

Published: Jan. 5, 2023

In the search for small-molecule aldose reductase (AR) inhibitors, new tetrazole-hydrazone hybrids (1-15) were designed. An efficient procedure was employed synthesis of compounds 1-15. All hydrazones subjected to an in vitro assay assess their AR inhibitory profiles. Compounds 1-15 caused inhibition with Ki values ranging between 0.177 and 6.322 µM IC50 0.210 0.676 µM. 2-[(1-(4-Hydroxyphenyl)-1H-tetrazol-5-yl)thio]-N'-(4-fluorobenzylidene)acetohydrazide (4) most potent inhibitor this series. Compound 4 markedly inhibited (IC50 = 0.297 µM) a competitive manner (Ki compared epalrestat 0.857 µM, 0.267 µM). Based on data obtained by applying MTT test, compound showed no cytotoxic activity toward normal (NIH/3T3) cells at tested concentrations, indicating its safety as inhibitor. exhibited proper interactions crucial amino acid residues within active site AR. silico QikProp all also determined pharmacokinetic Taken together, stands out promising further vivo studies.

Language: Английский

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Recent Developments in Enantioselective Domino Reactions. Part B: First Row Metal Catalysts

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(6), P. 768 - 819

Published: Jan. 17, 2023

This review updates the field of enantioselective domino reactions promoted by chiral catalysts derived from first row metals, such as zinc, iron, copper, scandium, nickel, cobalt, titanium, chromium and magnesium special case, published since beginning 2019. It illustrates how much a diversity these allow an impressive range novel highly many types to be achieved, providing one-pot access very complex functionalized molecules simple starting materials.

Language: Английский

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Synthesis, antimicrobial and cytotoxic activities of tetrazole N-Mannich base derivatives: Investigation of DFT calculation, molecular docking, and Swiss ADME studies

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1300, P. 137239 - 137239

Published: Dec. 3, 2023

Language: Английский

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Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid

Science China Chemistry, Journal Year: 2019, Volume and Issue: 63(1), P. 47 - 54

Published: Oct. 22, 2019

Language: Английский

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Divergent Synthesis of Enantioenriched β-Functional Amines via Desymmetrization of meso-Aziridines with Isocyanides

Organic Letters, Journal Year: 2019, Volume and Issue: 21(15), P. 6096 - 6101

Published: July 24, 2019

A highly enantioselective ring-opening desymmetrization of meso-aziridines with isocyanides was achieved in the presence a chiral N,N′-dioxide/Mg(OTf)2 complex. The situ generated 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous H2O TMSN3, enabling collective synthesis various vicinal amino-oxazoles, spiroindolines, β-amino amides, tetrazole derivative moderate to high yields excellent enantioselectivities.

Language: Английский

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Advances in Tetrazole Synthesis – An Overview

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(29)

Published: Aug. 3, 2022

Abstract Most of the active pharmaceutical ingredients (API) contain tetrazole ring, thus making them vast significance in new drug design descriptors. With this importance view, enormous studies are being carried out on synthesis derivatives. The methods its [3+2] cycloaddition, multicomponent reactions, microwave‐assisted using heterogeneous and homogeneous catalysts. Hence, it is necessary to highlight green catalysis that would be more environmentally benign economically viable. In review, we discuss processes presence These catalytic materials gave higher product yield a shorter reaction time were reusable.

Language: Английский

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Multicomponent reactions for the synthesis of tetrazole derivatives: Discovery and validation of a novel anticancer agent active against ER positive cancers

Results in Chemistry, Journal Year: 2024, Volume and Issue: 7, P. 101470 - 101470

Published: Jan. 1, 2024

Chemotherapy is an indispensable tool in medicine where small molecules act as potential cytotoxic, apoptotic, anti-angiogenic and anti-invasive agents targeting cancer cells. Chemotherapeutic possessing these multifaceted properties are highly warranted now the mortality rate increasing alarmingly. Tetrazole derivatives well known for their pharmacological activity against various types of progression. Herein, six tetrazoles were synthesised by multicomponent reactions (MCR) assessed vitro anticancer effects. Cytotoxic profiling compounds demonstrated that active a panel cells with highest anti-proliferative action MCF-7. Among compounds, DTS 3 Chlorine atom higher cytotoxic effects, which was selected further investigations. Molecular docking simulation analysis revealed preferential binding affinity to CDK6;suggesting its likely role CDK 6 inhibitor. Interestingly, entire series found be more potent expressing estrogen receptors, suggesting dependence on ER signaling cascade. Further exert effects well, among possessed maximal anti-proliferative, anti-apoptotic, possible promising multi-faceted anti-cancer agent.

Language: Английский

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Photocatalytic Deoxygenative Carboimination towards Functionalized Pyrrolines by Using Unstrained γ,δ‐Unsaturated Oximes

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(8), P. 2110 - 2116

Published: March 2, 2021

Abstract Photocatalytic deoxygenative carboimination of unstrained γ , δ ‐unsaturated oximes with π ‐acceptors including trifluoromethyl alkenes, 1‐trifluoromethyl‐1,3‐butadienes, gem ‐difluoroalkenes, acrylates, and styrenes has been achieved which provides an efficient mild approach to construct structurally diverse highly functionalized pyrrolines good functional group tolerance. Importantly, upon utilization alkenes as the coupling partners, developed protocol not only allows introduction extremely valuable ‐difluoroalkene functionality pyrroline moiety into one molecule, but could also further transform resulting ‐difluoroalkene‐functionalized architecturally intriguing indolizine alkaloids via oxidation/reduction sequential C−F bond cleavage. The mechanistic studies indicated that a free‐radical anionic process was probably involved in this photocatalytic transformation. magnified image

Language: Английский

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Enantioselective Synthesis of Azetidines through [3 + 1]-Cycloaddition of Donor–Acceptor Aziridines with Isocyanides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(7), P. 1513 - 1517

Published: Feb. 11, 2022

The enantioselective [3 + 1]-cycloaddition of racemic donor-acceptor (D-A) aziridines with isocyanides was first realized under mild reaction conditions using a chiral N,N'-dioxide/MgII complex as catalyst, providing facile route to enantioenriched exo-imido azetidines good excellent yield (up 99%) and enantioselectivity 94% ee). An obvious amplification effect observed in this system, an explanation elucidated based on the experimental investigation X-ray crystal structure enantiomerically pure catalyst.

Language: Английский

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