Tetrahedron最新文献

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Synthesis of benzimidazo[1,2-c]quinazolin-6(5H)-one derivatives via copper-mediated C–H isocyanatation of 2-arylbenzimidazoles 通过铜介导的 2-芳基苯并咪唑 C-H 异氰酸化合成苯并咪唑并[1,2-c]喹唑啉-6(5H)-酮衍生物

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-03-03 DOI: 10.1016/j.tet.2025.134569

Ali Nasirpour, Zarrin Ghasemi

An efficient protocol is disclosed for the synthesis of benzimidazo[1,2-c]quinazolin-6(5H)-ones utilizing an atom-economical C–H functionalization method. Copper-mediated isocyanatation of the aryl ring of the prepared 2-arylbenzimidazole derivatives, followed with intramolecular cyclization reaction resulted in the desired products. We diversified and purified the products without chromatography.

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New NHC–Pd complexes bearing bulky steric hindrance: Synthesis and catalytic activity in the Heteroaryl–Heteroaryl Buchwald–Hartwig amination reaction

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-03-01 DOI: 10.1016/j.tet.2025.134567

Xian-Fei Deng, Yan-Jun Chen, Li-Yu Yi, Ju Huang

New bulky N-heterocyclic carbene (NHC) palladium complexes {[Pd-PEPPSI-IPr^tBuDBB]} were synthesized and characterized. The catalytic activity of the palladium complexes was evaluated via the direct C–N arylation of N-heteroaryl amines with aryl chlorides in aerobic conditions at 100 °C. Under the optimal conditions, 2 mol% of the bulky palladium was found to be very efficient and produced the desired cross-coupling products in high yields.

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Sonochemically synthesized copper chelate from expired streptomycin sulfate as a sustainable catalyst for green synthesis of 1,4-disubstituted triazoles in aqueous medium

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-28 DOI: 10.1016/j.tet.2025.134564

Neetu Mev , Yachana Jain , Lalita Yadav , Priya Sharma , Madhu Agarwal , Ragini Gupta

This research work introduces a pioneering strategy for harnessing the potential of expired streptomycin sulfate as its copper chelate to catalyze the synthesis of biologically important 1,4-disubstituted-1,2,3-triazoles efficiently. The efficacy of this catalyst is showcased by the sonochemical 1,3-dipolar cycloaddition process, yielding 1,4-disubstituted-1,2,3-triazoles at 40 °C using a promotor ligand l-phenylalanine within 30 min in >90 % yield in aqueous media with high purity. The biocompatible promoter ligand assists the STR Cu chelate to enhance the reaction rate by stabilizing the Cu(I) oxidation state and preventing its undesirable disproportionation, thus increasing the yield of the intended product. The synthesized catalyst demonstrates extensive substrate compatibility and works equally well with precursors containing both electron donating and withdrawing groups (4–25). Additionally, all the synthesized compounds, as well as the catalyst, have been duly characterized by the usual analytical and spectroscopic techniques. Furthermore, the catalyst could be reused up to four cycles without a significant reduction in its catalytic performance.

这项研究工作介绍了一种开创性的策略，利用过期硫酸链霉素作为其铜螯合物的潜力，高效催化合成具有重要生物意义的 1,4-二取代-1,2,3-三唑。这种催化剂的功效体现在声化学 1,3 双极环加成过程中，使用促进配体苯丙氨酸，在水介质中于 40 °C 下 30 分钟内生成 1,4-二取代-1,2,3-三唑，收率达 90%，纯度高。生物相容性促进配体通过稳定 Cu（I）的氧化态并防止其发生不应有的歧化反应，协助 STR Cu 螯合物提高反应速率，从而提高了预期产物的产率。合成的催化剂具有广泛的底物兼容性，对含有电子供体和电子汲取基团（4-25）的前体同样有效。此外，所有合成的化合物和催化剂都已通过常用的分析和光谱技术进行了适当的表征。此外，催化剂可重复使用四次，而其催化性能不会明显降低。

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引用次数: 0

Electrocatalytic diazidation of alkenes with modified electrodes coated by Cu nanoparticles

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-28 DOI: 10.1016/j.tet.2025.134563

Xinglei He , Xiaobin Zhu , Luyao Wang , Jingheng Li , Chunlong Yu , Ke-Yin Ye

Vicinal diamines are an important structural motif that has been widely used in biological, medicinal, and materials science. Transition-metal-catalyzed diazidation of alkene is a straightforward and efficient approach for vicinal diamines, which are unfavorably associated with excess oxidants and limited substrate scope for electron-deficient alkenes. Herein we report an electrocatalytic diazidation of alkenes with the electrode coated by Cu nanoparticles pyrolyzed from Cu(salen)-based metal-organic framework. This strategy is compatible with various alkenes including those electro-deficient ones. Remarkably, the modified electrode maintains high electrocatalytic activity for diazidation even after 15 cycles.

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Convenient synthesis, characterization, evaluation and molecular docking of some new fused pyrazolo[3,4-d]pyrimidine derivatives and 3-methyl-8 phenylpyrazolo[3′,4':4,5]pyrimido[6,1-c][1,2,4]triazines against HeLa cancer cells

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-28 DOI: 10.1016/j.tet.2025.134557

Mirna T. Helmy, Mohamed A. Mohamed Teleb, Demiana H. Hanna, Mohamed W. El-Maadawy, Hamdi M. Hassaneen, Monica G. Kamel

Utility of the precursors 3-aryl-4-imino-1-phenylpyrazolo[3,4-d]pyrimidin-5-amines 4a-f and 3-aryl-4-hydrazineyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidines 5a-f in the synthesis of pyrazolo[3,4-d]pyrimidin-4-yl)hydrazono derivatives 10a-l via reaction of the hydrazines 5a-f with each of pyruvic acid or ethyl pyruvate 9. Refluxing of the hydrazone derivatives 10a-l in N,N-dimethylformamide for 90 h afforded the corresponding 3-methyl-8-phenylpyrazolo-[3′,4':4,5]pyrimido[6,1-c][1,2,4]triazine derivatives 11a-f. The cytotoxic results showed that the compound 11a was the most effective in suppressing the growth of HeLa cancer cells when compared to all other prepared compounds, with the most effective IC₅₀ value (3.46 ± 0.59 μg/mL) and no cytotoxic effects on normal human lung cells (WI-38). Moreover, the toxicity of the compound 11a against HeLa cells was confirmed by a significant increase in LDH levels in treated HeLa cells compared to untreated ones. Using annexin V/PI, treated HeLa cells with this IC₅₀ value of compound 11a displayed a considerable increase in early and late apoptotic cells in comparison to control cells. Additionally, apoptosis induction in the compound 11a-treated cells was mediated through increased reactive oxygen species (ROS) production. Moreover, the compound 11a markedly decreased the levels of antioxidant enzymes, including GSH, CAT, and SOD, in treated HeLa cells relative to untreated cells. Finally, the compound 11a markedly raised the expression levels of cleaved caspase-3, which is the initiator of apoptosis. Overall, these findings indicate that the compound 11a triggers significant cytotoxicity in HeLa cell cancer cells in a dose-dependent manner, primarily via ROS-mediated cell death, possibly via the mitochondrial pathway. So, compound 11a can be used as a promising treatment option for HeLa cancer in humans. In addition, in silico modelling, including, bioavailability, ADMET analysis, molecular docking and molecular dynamics simulation was conducted to evaluate the drug-likeness of the novel compounds (10a-11f). Compound 11a exhibited a promising binding affinity and stability against the receptors affirming its ability to act as antitumor and antioxidant ligand.

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引用次数: 0

Recent advances in the syntheses and reactions of biologically promising β-lactam derivatives

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-28 DOI: 10.1016/j.tet.2025.134565

Rajarshi Sarkar , Dripta De Joarder , Chhanda Mukhopadhyay

<div><div>Beta-lactam antibiotics are among the most widely used and effective classes of antimicrobial agents in clinical medicine, and their synthesis and reactions are crucial for their continued development and optimization. The beta-lactam ring structure, characterized by a four-membered cyclic amide, is the core functional group responsible for the antimicrobial activity of these compounds. This structure is found in a variety of antibiotic classes, including penicillins, cephalosporins, monobactams, and carbapenems, which collectively represent a cornerstone in the treatment of bacterial infections. The synthesis and reactivity of beta-lactams are central to both their mechanism of action and their therapeutic efficacy, making them a focal point for ongoing research in drug design and resistance management. The synthesis of beta-lactams typically involves complex organic reactions, often requiring careful control of steric and electronic factors to ensure the correct formation of the beta-lactam ring. One key synthetic challenge is the generation of the beta-lactam ring itself, which can be achieved through various methods, including nucleophilic acylation, cyclization reactions, and enzymatic pathways. These synthetic routes must overcome significant hurdles, such as maintaining the stability of the reactive intermediate and controlling the regiochemistry of subsequent functional group additions. Advances in synthetic techniques, including the use of combinatorial chemistry, have led to the development of novel beta-lactam derivatives with improved pharmacological properties and expanded antibacterial spectra. The reactivity of beta-lactams, particularly their susceptibility to hydrolysis, plays a critical role in their mechanism of action. The beta-lactam ring undergoes nucleophilic attack by bacterial enzymes called beta-lactamases, which hydrolyze the amide bond and deactivate the antibiotic. The ability of beta-lactams to bind and inhibit bacterial cell wall synthesis, specifically the enzyme transpeptidase (also known as penicillin-binding protein, or PBP), is essential for their bactericidal activity. This interaction prevents the cross-linking of peptidoglycan, a critical component of the bacterial cell wall, leading to cell lysis and death. The reactivity of the beta-lactam ring toward PBPs is highly selective, and this specificity has made beta-lactams a valuable tool in treating infections caused by a wide range of bacterial pathogens. However, the increasing prevalence of bacterial resistance, particularly through the production of beta-lactamase enzymes, has prompted the development of beta-lactamase inhibitors and the design of new beta-lactam derivatives with enhanced stability against these enzymes. These inhibitors, such as clavulanic acid and tazobactam, act by irreversibly binding to the beta-lactamase enzyme, restoring the effectiveness of beta-lactam antibiotics. Ongoing research into the synthesis and reactivity of be

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引用次数: 0

Reaction of acylpropargylic alcohols with 1-pyrrolines: A synthetic and quantum-chemical study

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-28 DOI: 10.1016/j.tet.2025.134566

Ludmila A. Oparina, Anton V. Kuzmin, Lyudmila A. Grishchenko, Nikita A. Kolyvanov, Igor’ A. Ushakov, Boris A. Trofimov

The reactions of acylpropargylic alcohols with 1-pyrrolines (60 °C, 2−3 h) afford the acylethenyltetrahydropyrrolo[2,1-b]oxazoles and furan-3(2H)-ylideneaminoalkanones in 55–76 % and in trace to 12 % yields, respectively. Quantum-chemical calculations (B2PLYP-D3) show that formation of pyrrolo[2,1-b]oxazoles is kinetically more preferable than that of furan-3(2H)-imines, the latter being formed through 1,3(4)-dipole and 2-hydroxypyrrolidine intermediates.

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Synthesis of benzofuro[3,2-c]quinolinones via one-pot reaction of 3-chlorooxindoles and salicylaldehydes

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-27 DOI: 10.1016/j.tet.2025.134568

Feng Wang , Sheng-Bin Wang , Jia-Qi Pan , Qiu-Yu Ma , Mingshu Wu , Rui Ning

A mild and efficient one-pot reaction for constructing benzofuro[3,2-c]quinolinones from 3-chlorooxindoles and salicylaldehydes is presented. The method involves the base-mediated formation of a dihydrobenzofuran spirooxindole intermediate, which is subsequently converted into benzofuro[3,2-c]quinolinones facilitated by TfOH. This strategy is characterized by transition metal-free conditions, easily accessible starting materials, and a broad substrate scope.

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3-Fluorooxindoles from indolin-2-ones by Selectfluor

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-26 DOI: 10.1016/j.tet.2025.134556

Hui Qin , Guo-Liang Wei , Fu-Wei Wang , Xiao-Hong Mao , Mei-Hua Bao , Yi-Wen Zhang , Ping Huang , Xiao-Wei Zheng

Herein, a practical and efficient method for fluorinating various indolin-2-ones under mild conditions was presented, utilizing selectfluor as a cost-effective fluorination reagent. Notably, the protocol operated under environmentally friendly conditions, facilitating the generation of various substituted indolin-2-ones into corresponding fluorinated indolin-2-ones in moderate to good yields, all without the need for an alkali source or heating.

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Efficient on-water synthesis of novel pyrano[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines via catalyst-free one-pot three-component reaction

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron

Pub Date : 2025-02-25 DOI: 10.1016/j.tet.2025.134559

Fatemeh Hamidi Dastjerdi, Abbas Ali Esmaeili

An efficient, catalyst-free and eco-friendly synthesis of novel pyrano[3,2-e][1,2,4]triazolo[1,5-a]pyrimidines via cyclo-condensation of [1,2,4]triazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione, aromatic aldehydes, and malononitrile has been described using ‘‘On-water” concept. The use of water as a clean media, catalyst-free conditions, excellent functional group acceptance, easier product isolation/purification without column chromatography, short reaction times, and good-to-excellent yields are the remarkable privileges of this protocol. Finally, ¹H, ¹³C NMR, IR, mass spectra, and elemental analyses were conducted to determine the products’ structure.

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