Synthesis of Some 2-(3-Alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles as Novel Antibacterial Agents

Kumar, Sunil; Aggarwal, Ranjana; Sharma, Chetan

doi:10.1080/00397911.2015.1062986

Cited by 9 publications

(1 citation statement)

References 43 publications

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“…The structure of regioisomers 190 was unambiguously characterized by 19 F and 13 C NMR spectroscopy. 13 [146] Similarly, Kataria et al regioselectively synthesized dihydropyrazole-1-thiocarboxamides, from trifluoromethyl-β-diketones and thiosemicarbazide in refluxing ethanol and explored for their interactions with plasma protein. [147] Rai et al developed a class of pyrazole based inhibitors of human lactate dehydrogenase (LDH).…”

Section: Pyrazole Derivativesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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Section: Pyrazole Derivativesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

et al. 2021

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Bovine serum albumin (BSA) serves as a model protein to explore drug‐protein interactions due to its structural similarities with Human serum albumin (HSA). In this report, the binding tendency of BSA protein with synthesized trifluoromethyl functionalized pyrazoles i. e., 5‐hydroxy‐3‐(p‐methoxyphenyl)‐5‐trifluoromethyl‐4,5‐dihydropyrazole‐1‐thiocarboxamide (2 a) and 5‐hydroxy‐3‐(p‐bromophenyl)‐5‐trifluoromethyl‐4,5‐dihydropyrazole‐1‐thiocarboxamide (2 b) was explored using spectroscopic techniques. The pyrazoles were synthesized by a one‐pot reaction and characterized with the help of single‐crystal X‐ray diffraction. The crystallographic parameters were found to be in close agreement with those evaluated computationally using density functional theory (DFT). Further, to explore the nature of interactions involved in binding, Hirshfeld surface analysis was carried out, which indicated the presence of non‐covalent interactions. Specifically, hydrogen bonding viz O−H, S−H and F−H were observed in both cases. As predicted by DFT based global reactivity descriptors, compound 2 a is chemically softer than 2 b. In silico molecular docking and molecular dynamic studies were also performed to validate the nature of binding interactions present in both cases.

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3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

et al. 2022

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Compounds containing the coumarin scaffold are widely used in the pharmaceutical and medicinal industries. The biological activities of coumarin containing derivatives make the attractive for the develop new drugs. Different methods and techniques are developed to synthesize new drugs using coumarin as a starting material. This review summarized various methods, techniques and reaction conditions for synthesis of coumarins containing compounds from 3‐bromoacetylcoumarin. A total of 79 coumarin intermediates and products are reported herein. The different reactions include nucleophilic substitutions, one‐pot and multi‐step synthesis for preparation of coumarin containing compounds through different mechanisms and the outcomes achieved through such reactions are discussed. The prepared compounds showed a range of activities resulting in antifungal, antimicrobial, anti‐inflammatory, antidiabetic and cholinesterase inhibitors. The nucleophilic substitution reactions involving urea related compounds, followed by intramolecular cyclization lead to imidazole and thiazole moieties, which exhibit antibacterial activities. It is hoped that this review provides useful insight for researchers engaged in this field to expand the knowledge gained in this area.

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Synthesis of Some 2-(3-Alkyl/aryl-5-trifluoromethylpyrazol-1-yl)-4-(coumarin-3-yl)thiazoles as Novel Antibacterial Agents

Cited by 9 publications

References 43 publications

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Experimental and Computational Validation of Structural Features and BSA Binding Tendency of 5‐Hydroxy‐5‐trifluoromethyl‐3‐arylpyrazolines**

3‐Bromoacetylcoumarin, a Crucial Key for Facial Synthesis of Biological Active Compounds

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