Thiazole: A promising heterocycle for the development of potent CNS active agents

Mishra, Chandra Bhushan; Kumari, Shikha; Tiwari, Manisha

doi:10.1016/j.ejmech.2014.12.031

Cited by 164 publications

(78 citation statements)

References 136 publications

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“…In the recent years, attention has been increasingly paid to the synthesis of novel mono‐heterocyclic and bis‐heterocyclic derivatives expected to exhibit various biological activities . In the light of these data and in continuation of our program, we have recently reported the synthesis of some new bis‐heterocyclic compounds of biological interest .…”

Section: Introductionmentioning

confidence: 98%

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Metwally

Abdelrazek

Eldaly

et al. 2015

Journal of Heterocyclic Chem

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3‐(3,5‐Dimethyl‐1 H ‐pyrazol‐1‐yl)‐3‐oxopropanenitrile 1 was used as a cyanoacetylating agent for synthesis of the acetanilide derivative 3. Compound 3 was utilized as a key intermediate for the synthesis of some new mono‐chromene and di‐chromene derivatives 9 and 13, the dihydrazo derivatives 15, and the dithiazole derivatives 18 via the condensation with o‐hydroxybenzaldehyde derivatives, the coupling with aryl diazonium salts, or the reaction with phenyl isothiocyanate in presence of KOH followed by phenacyl bromide derivatives respectively.

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Section: Introductionmentioning

confidence: 98%

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Metwally

Abdelrazek

Eldaly

et al. 2015

Journal of Heterocyclic Chem

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“…Thiazoles play an important role in designing new compounds of medical importance with their great usefulness owing to a very wide variety of applications ranging from bacteriostatic agents, antibiotics, and cytotoxic, antifungal, and inhibitory activities to central nervous systems active agents . In view of the importance of thiazoles and their derivatives, several methods for the synthesis of thiazole derivatives were developed by Hantzsch , Zoltewicz and Deady , Sammes , Elederfield , and Pola .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 2‐Aminothiazole Derivatives in Easy Two‐Step, One‐Pot Reaction

Dziuk

Kyzioł

Zaleski

et al. 2018

Journal of Heterocyclic Chem

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Condensation of brominated ethyl acetoacetate with thiourea gives 2‐amino‐5‐ethoxycarbonyl‐4‐methylthiazole (1) and ethyl α‐(2‐amino‐4‐thiazolyl)acetate (2), indicating that bromination of the substrate occurs on both sides of the carbonyl group. X‐ray diffraction studies indicate weak hydrogen bonds of the amino groups, which are not observed in the IR spectra. The 1 molecule adopts planar S,O‐anti conformation in the crystal lattice, whereas the methylene group, insulating thiazole ring and the ester group in 2 molecule, makes it more flexible and makes the ester group nearly perpendicular to the thiazole ring. The small deviations of the bond lengths and angles indicate mesomeric interaction between complementary substituents across the thiazole ring.

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“…Thiazole is one of the most important class of heterocyclic rings bearing sulphur and nitrogen atoms . Its fusion with other moieties has proved its meticulous position in chemistry and drugs fields, because of its potential biological activities exhibited with lesser side effects, such as antimicrobial, anticonvulsant, antibacterial, anticancer, and antioxidant properties. Especially, antioxidant is one of the familiar biological property shown by thiazole derivatives and are highly conspicuous with its biological relevance.…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, DFT, Vibrational Spectra with Fluorescence Effect, Hirshfeld Surface, Docking Simulation and Antioxidant Activity of Thiazole Derivative

et al. 2019

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2‐(4‐methylphenoxy)‐N‐(4‐(4‐bromophenyl) thiazol‐2‐yl) acetamide compound was obtained via a multistep synthesis sequence processes, which is characterized by 1H NMR, 13C NMR and its three‐dimensional structure has been confirmed by single crystal X‐ray diffraction method. The supramolecular structure of the molecule revealed the stability of crystal packing with diverse intermolecular interactions. Density functional theory calculations (DFT) at B3LYP 6–311++G(d,p) level has been used to predict the molecular geometry and were in good agreement with the experimental data. Moreover, the theoretical calculations were carried out to appraise the electronic structure, vibrational spectra, natural bond orbital analysis, molecular electrostatic potential, frontier molecular orbitals and global reactivity descriptors. Raman spectra with fluorescence effect was examined with visible and near IR excitation wavelengths. Hirshfeld surface and energy framework analysis revealed the important intermolecular contacts and interaction energies. The antioxidant activity of this synthesized compound was predicted by in silico docking study on human peroxiredoxin 5 protein. The potential antioxidant activity was investigated by 1,1‐diphenyl‐1‐picrylhydrazyl (DPPH) free radical screening and compared with standard drug ascorbic acid.

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Thiazole: A promising heterocycle for the development of potent CNS active agents

Cited by 164 publications

References 136 publications

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

3‐(3,5‐Dimethyl‐1H‐Pyrazol‐1‐yl)‐3‐Oxopropanenitrile as Precursor for Some New Mono‐Heterocyclic and Bis‐Heterocyclic Compounds

Synthesis of 2‐Aminothiazole Derivatives in Easy Two‐Step, One‐Pot Reaction

Molecular Structure, DFT, Vibrational Spectra with Fluorescence Effect, Hirshfeld Surface, Docking Simulation and Antioxidant Activity of Thiazole Derivative

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