Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation

Prabhudeva, M. G.; Kumara, Karthik; Kumar, A. Dileep; Ningappa, Mylarappa; Lokanath, N.K.; Kumar, K. Ajay

doi:10.1007/s11164-018-3501-2

Cited by 12 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A two-step synthesis of different tri-substituted pyrazole products was performed. In the first step, the required chalcones, 3 ( a-f ) were prepared from thiophene-2-aldehyde 1 , with various substituted acetophenone, 2 ( a-f ) in line with our earlier report [ 34 ]. In the second step, the chalcones 3 ( a-f ) were subjected to Amberlyst-15 (10%, w/w) catalyzed (3 + 2) annulation reaction with phenylhydrazine hydrochloride 4 ( a-b ) in acetonitrile as solvent.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

Kumara

Prabhudeva

Vagish

et al. 2021

Heliyon

Self Cite

View full text Add to dashboard Cite

In a sustained search for novel and effective antioxidants, a potential therapeutic leads against renal, and neurological disorders. Amongst the heterocycles, pyrazole and their derivatives have been extensively studied for their biological potencies, particularly to a larger extent for their antioxidant properties. Although many of pyrazole derivatives displayed antioxidant activities, still there is a need of developing efficient protocol for their synthesis, involving ecofriendly conditions, molecules of greater antioxidant efficacy and lesser toxicity, etc. In this context, the current study presents an amberlyst-15 catalysed efficient synthesis of 2-pyrazoline derivatives, 5 ( a - g ) via (3 + 2) annulation of chalcones with phenylhydrazines. Structure proofs of new pyrazoles offered by spectral studies, and the molecular structure of compound 5d of the series by crystallographic studies, which revealed an intra molecular hydrogen bond interactions (C–H⋯N type), and stabilization by C–H...π and π---π molecular interactions. Of the series, compounds 5g and 5h show excellent DPPH (IC 50 = 0.245 ± 0.01, and 0.284 ± 0.02 μM); and hydroxyl (IC 50 = 0.905 ± 0.01, and 0.892 ± 0.01μM) radical scavenging activities comparable with respective controls, ascorbic acid (IC 50 = 0.483 ± 0.01μM) and BHA (IC 50 = 1.739 ± 0.01μM). The molecular docking and ADME/Tox studies indicate that, these compounds have good antioxidant activity through π-π stacking with Catalase via Try337 and Phe140, and therefore, might be lead antioxidants for further study.

show abstract

Section: Resultsmentioning

confidence: 99%

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

Kumara

Prabhudeva

Vagish

et al. 2021

Heliyon

Self Cite

View full text Add to dashboard Cite

show abstract

“…Simply, many pyrazoline compounds have been derived from chalcones via condensation with hydrazine, phenylhydrazine, hydrazide, thiohydrazid, semi-carbazide, and thio-semicarbazide derivatives using ethanol and sometimes in existence suitable catalysts such as sodium hydroxide or glacial acetic acid. [90] Figure 3 A Recently, versatile chalcone-based pyrazoline derivatives have been reported as beneficial compounds for treating different diseases, for example, anticancer compound 11 [91], antimalarial-antibacterial compound 12 [92], and antiinflammatory compound 13 [93].…”

Section: Chemical Derivatization Of Chalconesmentioning

confidence: 99%

Recent Updates on Synthetic Strategies of Chalcone Scaffold and their Heterocyclic Derivatives

Amin

Shaykoon

Marzouk

et al. 2023

Journal of advanced Biomedical and Pharmaceutical Sciences

View full text Add to dashboard Cite

Chalcones, α,β-unsaturated ketone linking two aromatic moieties gained noticeable attention in the medicinal chemistry area. Chalconescaffold construction has proceeded via verified chemical synthetic strategies, including condensation, coupling, olefination, acylation, reductive annulation, one-pot, and Fries' rearrangement methods. Specific approaches have assisted chalcone combinations using microwave radiation and ultrasound waves to enhance synthetic conditions and amplify yields. Recently, chalcones have been investigated extensively as core structures in potent bioactive hybrids such as anticancer, antimicrobial, and others. In addition, chalcones serve as parent structures for synthesizing several bioactive heterocyclic derivatives comprising five-membered and six-membered rings. This review will discuss recent applications of chalcones' synthetic strategies, physical and chemical characters, biological activities, and chemical derivatization.

show abstract

“…On the contrary, the most potent analogs 33 (Figure 5) having a 2‐methyl group in the thiophene ring had a different substitution pattern of the phenyl moiety at position 5 of pyrazoline ring. [ 47 ] In this case, compounds 33 (R = H, F or Cl) were very efficient (MIC values between 15 and 25 μg/ml) against E. coli , B. subtilis , A. niger and A. flavus , but their activity against S. aureus and C. albicans was poor (MIC values between 80 and 120 μg/ml).…”

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

Thiophene‐containing compounds with antimicrobial activity

Roman¹

2022

Archiv der Pharmazie

View full text Add to dashboard Cite

Thiophene, as a member of the group of five-membered heterocycles containing one heteroatom, is one of the simplest heterocyclic systems. Many synthetic strategies allow the accurate positioning of various functionalities onto the thiophene ring. This review provides a comprehensive, systematic and detailed account of the developments in the field of antimicrobial compounds featuring at least one thiophene ring in their structure, over the last decade.

show abstract

Amberlyst-15 catalyzed synthesis of novel thiophene–pyrazoline derivatives: spectral and crystallographic characterization and anti-inflammatory and antimicrobial evaluation

Cited by 12 publications

References 20 publications

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

Design, synthesis, characterization, and antioxidant activity studies of novel thienyl-pyrazoles

Recent Updates on Synthetic Strategies of Chalcone Scaffold and their Heterocyclic Derivatives

Thiophene‐containing compounds with antimicrobial activity

Contact Info

Product

Resources

About