A Rapid, Four-Component Synthesis of Functionalized Thiazoles

Sabbaghan, Maryam; Alidoust, Mostafa; Hossaini, Zinatossadat

doi:10.2174/138620711796957134

Cited by 7 publications

(7 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In connection with our previous work for the synthesis of zinc oxide nanostructures [31] and our interest in heterocyclic synthesis [32][33][34][35], we report an efficient synthesis of functionalized pyrroles. Thus, the reaction of alkylamines 1 with dialkyl acetylenedicarboxylates 2 and a-chloroketones 3 in the presence of ZnO nanorods (ZnO-NRs, 12 % mol) as catalysts without adding any organic solvent at 70°C led to polysubstituted pyrroles 4 in excellent yields (Scheme 1).…”

Section: Resultsmentioning

confidence: 84%

Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

et al. 2015

Self Cite

View full text Add to dashboard Cite

An efficient zinc oxide nanorod-catalyzed onepot strategy has been developed for the synthesis of polysubstituted pyrroles in very good yields. The present approach provides a three-component reaction between primary alkylamines, dialkyl acetylenedicarboxylates, and 2-chloro-1,3-dicarbonyl compounds with several advantages such as short reaction time, high yields, solvent free, and little catalyst loading. After reaction course, ZnO nanorods can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence eco-friendly. Graphical abstract

show abstract

Section: Resultsmentioning

confidence: 84%

Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…First, the selected secondary amines were converted to the corresponding thioureide compounds ( A ) with benzoyl chloride/ammonium thiocyanate and reacted with α‐bromoacetophenone derivatives ( B ) to provide the final 2,4,5‐thiazole compounds ( 1‐44 ). According to the applicated synthetic procedure, first nucleophilic alkylation reaction occurs through sulfur atom via 2‐bromoacethophenone. After HBr elimination and subsequent enolization, the obtained intermediate product undergoes intramolecular cyclization.…”

Section: Resultsmentioning

confidence: 99%

Novel thiazole‐piperazine derivatives as potential cholinesterase inhibitors

Demirayak

Şahin

Ertaş

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Dementia is a cognitive disorder mostly associated with Alzheimer's disease (AD) in addition to being seen in many other diseases of the central nervous system (CNS). The limited number of drugs is not sufficient to provide adequate improvement to increase the quality of life of patients suffering from this symptom; therefore, all treatment options should be evaluated in detail. In this study, new molecules, [2‐(4‐(2/3/4‐substituted phenyl)piperazin‐1‐yl)‐4‐phenylthiazol‐5‐yl][3/4‐substituted phenyl]methanone derivatives (1‐44), were obtained and analyzed in terms of their anticholinesterase activities. Kinetic mode and molecular interactions were also evaluated. An enzyme inhibition study was undertaken on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) using the Ellman method. Maestro program was used in molecular modeling studies. Forty‐four compounds were evaluated on AChE and BChE enzymes at 10−3 and 10−4 concentrations. The inhibition concentrations were calculated as 0.268μM to 2.104μM for six compounds (4, 5, 16, 27, 37, and 38) on AChE. Compound 5 including the 4‐methoxy substituent (IC50: 0.268μM) and compound 38 containing the 4‐methoxy and 3‐methyl substituents (IC50: 0.286μM) showed the highest AChE inhibitory activity. They were further examined in terms of hydrogen bonding with Arg296 and Ar‐Ar interaction with Trp286. The activity of compound 5 was also assessed in mixed‐type kinetic mode.

show abstract

“…Since it came to 15-20 °C, it was poured into cold water (50 mL) and then, it was added to water and neutralization was made using NaHCO 3 . The final compounds dissolved and recrystallized using ethyl alcohol [17][18][19][20][21].…”

Section: Synthesis Of Target Compounds (3aa-af 3ba-bf 3cc-cf)mentioning

confidence: 99%

Synthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs

Şahin¹,

Biltekin²,

Yurttaş³

et al. 2020

Turk J Chem

View full text Add to dashboard Cite

Marine compound dendrodoine was first obtained from tunicate species ( Dendrodo grossularia ). It has a five-membered ring, namely, it is a heterocycle thiadiazole, which is found rarely in natural sources . Following its biological activities, novel analogs have been investigated recently. Synthesis of the analogs for this study is realized with uncommon thiazole closure, including methylene-carbonyl condensation. Structures are elucidated by NMR ( 1 , 13 C) and HRMS spectrums. As an alkaloid derivative, antioxidant properties were evaluated with DPPH and FRAP assays and antimicrobial effect with microdilution method. Among the series, 3bc-3cf showed higher antioxidant activity than those having 3 or 4-pyridyl substituents. There is lesser activity for 2-pyridyl activity for 2-pyridyl containing group, which may be a result of intramolecular interactions. No activity was observed against gram-negative bacteria at 250 μg/mL. 3ae and 3ce showed activity at 64 μg/mL against S. aureus and 3ae showed activity at 16 μg/mL against S. epidermidis gram-positive bacteria. Chloramphenicol showed activity against all microorganisms at 8–16 μg/mL. Sixteen original dendrodoine analogs have been defined by close/higher activity compared to dendrodoine analogs and Trolox.

show abstract

A Rapid, Four-Component Synthesis of Functionalized Thiazoles

Abstract: An efficient synthesis of 2-(dialkylamino)-4-phenyl)-1,3-thiazol-5-yl)(phenyl)methanone using acid chlorides, secondary amines, 2-bromoacethophenone and ammonium thiocyanate is described.

Cited by 7 publications

References 13 publications

Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

Solvent-free synthesis of polysubstituted pyrroles catalyzed by ZnO nanorods

Novel thiazole‐piperazine derivatives as potential cholinesterase inhibitors

Synthesis, antioxidant and antimicrobial properties of novel pyridyl-carbonyl thiazoles as dendrodoine analogs

Contact Info

Product

Resources

About