Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity

Havrylyuk, Dmytro; Zimenkovsky, Borys; Karpenko, Olexandr; Grellier, Philippe

doi:10.1016/j.ejmech.2014.07.103

Cited by 55 publications

(36 citation statements)

References 29 publications

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“…As shown in Figure 4, this compound exhibits two prominent bands in all selected solvents, appearing at 298-312 nm and 373-391 nm, respectively, and the molar absorption coefficient values are in the same range of 6×10 4 M -1 cm -1 . The shorter wavelength is ascribed to a localized aromatic π-π * transition and the long wavelength is attributed to ICT transitions [24].…”

Section: Optical Spectroscopymentioning

confidence: 82%

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Varghese

Al‐Busafi

Suliman

et al. 2017

SQU Journal for Science

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ABSTRACT:A novel ethoxy derivative of an amino acid chemosensor, 3-naphthyl-1-phenyl-5-(2ʹ-fluoro-5ʹ-nitrophenyl)-2-pyrazoline (NPFNP), has been synthesized and characterized by different spectroscopic methods. A single crystal of the ethoxy derivative, 3-naphthyl-1-phenyl-5-(2ʹ-ethoxy-5ʹ-nitrophenyl)-2-pyrazoline NPENP, has been obtained and characterized. The structure holds interest as it carries biologically active pyrazoline as a central ring attaching to electron donating and withdrawing substituents. The major motivation for this work was to gain detailed insight into the structural parameters of this compound for investigating the influence of crystal packing and geometrical dimensions on optical properties. Time-dependent DFT calculations have been employed for comparing the XRD data with theoretical parameters. The results show that the DFT method at B3LYP/6-31G level can well reproduce the structure of the title compound.Keywords: Pyrazoline; UV absorption; Crystal structure; Chemosensor; TD-DFT. ‫األمينيه‬ ‫األحماض‬ ‫كاشف‬ ‫تفاعل‬ ‫دراسة‬

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Section: Optical Spectroscopymentioning

confidence: 82%

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Varghese

Al‐Busafi

Suliman

et al. 2017

SQU Journal for Science

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“…25). 5-Pyrazoline substituted 4-thioxo-2-thiazolidinones 3.19 were obtained under the same conditions [98].…”

Section: The Main Approaches To the Synthesis Of 4-thiazolidinones Wimentioning

confidence: 99%

“…To continue the above mentioned study, 5-pyrazoline derivatives of 4-thiazolidinone 3.21 with oxoethylamino-methylene linker group were synthesized by modification of rhodanine-5carboxylic acid 3.20 in the reaction with pyrazolines and in the presence of DCC (dicyclohexylcarbodiimide) [98] (Fig. 26).…”

Section: The Main Approaches To the Synthesis Of 4-thiazolidinones Wimentioning

confidence: 99%

“…Target heterocycles were branched by the methylidene or oxoethylamino-methylidene linker groups. The results of screening against Trypanosoma brucei gambiense allowed to identify 5 compounds with sufficient antitrypanosomal activity (IC 50 has been directed on substitution of pyrazoline core and modification of N3-thiazolidinone position (4.73), elongation of linker group (4.74) and rhodanine-isorhodanine isomerism (4.75) [98].…”

Section: Antiviral and Antiparasitic Activity Of Pyrazoleethiazolidinmentioning

confidence: 99%

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Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline–thiazolidine-based hybrids

Havrylyuk

Roman

Lesyk

2016

European Journal of Medicinal Chemistry

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140

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The features of the chemistry of 4-thiazolidinone and pyrazole/pyrazolines as pharmacologically attractive scaffolds were described in a number of reviews in which the main approaches to the synthesis of mentioned heterocycles and their biological activity were analyzed. However, the pyrazole/pyrazoline-thiazolidine-based hybrids as biologically active compounds is poorly discussed in the context of pharmacophore hybrid approach. Therefore, the purpose of this review is to summarize the data about the synthesis and modification of heterocyclic systems with thiazolidine and pyrazoline or pyrazole fragments in molecules as promising objects of modern bioorganic and medicinal chemistry. The description of biological activity was focused on SAR analysis and mechanistic insights of mentioned hybrids.

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“…Pyrazolines are used as anticancer [18,19], antioxidant [20], antitumor [21], anti-inflammatory [22], trypanocidal [23], MAO-B inhibitors [24], agonist of cannabinoid receptors [25] and antidepressant agents [26]. Therefore, the pyrazoline motif makes up the core structure of numerous biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents

Dinesha

Viveka

Priya

et al. 2015

European Journal of Medicinal Chemistry

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Synthesis of pyrazoline–thiazolidinone hybrids with trypanocidal activity

Cited by 55 publications

References 29 publications

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Study on the Reactivity of Amino Acid Chemosensor, NPFNP, with Ethanol: Structural Elucidation through Single Crystal XRD and DFT Calculations

Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline–thiazolidine-based hybrids

Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents

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