Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents

Lv, Peng‐Cheng; Li, Huan‐Qiu; Sun, Juan; Zhou, Yang; Zhu, Hai‐Liang

doi:10.1016/j.bmc.2010.05.034

Cited by 251 publications

(115 citation statements)

References 25 publications

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“…The correlation equations for CH 3(keto) , H 4 , H 4 ′, H 5 , CH 2 , OCH 3 and CH 3(ester) proton chemical shifts (δ, ppm) are given in equations (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). …”

Section: Spectral Correlationsmentioning

confidence: 99%

“…This spatial arrangement of the protons was confirmed by 1 H NMR and XRD analysis. Many solvent assisted and solvent-free methods including cyclization [15,16], N-acetylation, N-thio-acetylation [17], Nphenylation [15], N-thio-amination [12,13] and condensation [14] were reported in the literature for synthesis of these pyrazoline derivatives. The catalysts such as, Lewis acids, weak acids [18], polyacids [19], sodium acetate [20], clays [21], fly-ash:H 2 SO 4 [14], SiO 2 -H 3 PO 4 [22], preheated fly-ash [12], fly-ash:PTS [13], with or without microwave and ultrasound irradiation [23] were utilized for the above reactions.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Synthesis and Spectral Correlation of 1N-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazolines

Thirunarayanan¹,

Sekar²

2017

MOCR

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Abstract.A series containing fourteen 1 N-acetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were synthesized by KF/Al 2 O 3 catalyzed solvent-free condensation of 1 Nacetyl-3-(4-hydroxyphenyl)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines and (E)-methyl-2-[2-(bromo methyl)-phenyl]-3-methoxyacrylate under microwave irradiation. The yields of the above 1 Nacetyl-3-(4-β-methacrylate)-5-(substituted phenyl)-4, 5-dihydro-1 H-pyrazolines were more than 90%. These pyrazolines were characterized by their physical constants, IR, NMR and Mass spectral data. The infrared spectral frequencies (ν, cm -1 ) and NMR chemical shifts (δ, ppm) of proton and carbons of these pyrazolines were assigned and correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses, the effects of substituent on the above spectral data have been discussed.Keywords: Solvent-free synthesis, KF/Al 2 O 3 , β-methacrylate-1 N-acetylpyrazolines, IR spectra, NMR spectra, Hammett correlation IntroductionThe 1 H-4,5-dihydropyrazoline and 1 N-acetyl-4,5-dihydroprazoline derivatives play structurally more important roles in pharmaceutical field of research because they possess numerous biological activities. were utilized for the above reactions. Now-a-days chemists and organic researchers have paid more attention to solvent-free methods. These methods are important and play vital role for synthesis of organics due to easy work-up procedure, technique, shorter time, less hazardousness, less pollution to the environment, higher yield. Sasikala et al.,[15] have synthesised some 5-chloro-2-thienyl based pyrazoline derivatives by solvent-free method and studied the antimicrobial activities. Sakthinathan et al.[20] have synthesised and studied the effects of substituent on 2-naphthyl based pyrazolines. Spectroscopic data were used for prediction of ground state equilibration of organic compounds such as, E, Z or cis-trans isomers of unsaturated compounds such as, alkenes, alkynes, polyenes, enol-enones, unsaturated acid chlorides, ω-halo-acyl compounds and pyrazoline derivatives. These spectroscopic data were applied for the study of spectral linear regression through Hammett equation. Thirunarayanan et al. have studied the effects of substituents and solventfree synthesis of some 5-bromo-2-thienyl based pyrazolines [22]. The solvent-free synthesis and the Modern

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Section: Spectral Correlationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solvent-Free Synthesis and Spectral Correlation of 1N-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-1H-Pyrazolines

Thirunarayanan¹,

Sekar²

2017

MOCR

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“…Pyrazoles and their derivatives have been known to exhibit a wide range of physiological and pharmacological activities, such as anti-inflammatory [38], antibacterial [39,40], anti-convulsant [41], anticancer [42,43], anti-depressant [44], anti-hyperglycemic [45], antiviral [46], antipyretic [47], antioxidant [48], antitubercular [49], fungicides [50], and analgesic activities [51]. These heterocycles have also found applications in transition-metal chemistry as an analytical reagent [52], ligand used for complexation with metals and as antioxidant additives to fuels [53,54].…”

Section: M806 (Page 2)mentioning

confidence: 99%

2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

Albooye

Kiyani

2013

Molbank

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Abstract:As a consequence of one-pot, three-component reaction of trans-2-benzoyl-3-(4-nitrophenyl)aziridine with 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and ammonium acetate, 2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene was achieved in good yield. The desired photochromic compound display interesting photochromic behavior in the crystalline and solution phase. The structure of the newly synthesized photochromic compound was characterized by elemental analysis, 1 H-NMR, 13 C-NMR and UV-Visible spectral data.

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“…[8][9][10] Although EGFR is involved in various physiological processes, and as such is expressed in non-malignant tissues, this tyrosine kinase has been shown to be over-expressed in tumors of epithelial origin such as colon, breast, ovarian, lung, and prostate cancer. [11][12] Consequently, EGFR overexpression in cancerous tissue presents an attractive target for compounds with inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

“…[10][11]13 Here, for the first time we report the synthesis of thiourea-functionalized silicon nanoparticles (SiNPs) as a new multifunctional nanoscale system. By developing such hybrid nanoparticles, we can exploit the unique optical properties of SiNPs whilst introducing the targeting characteristics of the thiourea ligand for diagnostic applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diagnostic Silicon Nanoparticles for Targeted Delivery of Thiourea to Epidermal Growth Factor Receptor-Expressing Cancer Cells

Behray

Webster

Pereira

et al. 2016

ACS Appl. Mater. Interfaces

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ABSTRACT:The novel thiourea-functionalized silicon nanoparticles (SiNPs) have been successfully synthesized using allylamine and sulforaphane, an important anticancer drug, followed by a hydrosilylation reaction on the surface of hydrogen terminated SiNPs. Their physiochemical properties have been investigated by photoluminescence emission, FTIR and elemental analysis. MTT assay has been employed to evaluate in vitro toxicity in colorectal cancer cells (Caco-2) and primary normal cells (CCD). The results show significant toxicity of thiourea SiNPs after 72 h incubation in the cancer cell line and the toxicity is concentration dependent and saturated for concentrations above 100 µg/mL. Confocal microscopy images have demonstrated the internalization of thiourea-functionalized SiNPs inside the cells. Flow cytometry data has confirmed receptor-mediated targeting in cancer cells. This nanocomposite takes advantage of the EGFR active targeting of the ligand in addition to the photoluminescence properties of SiNPs for bioimaging purposes. The results suggest that this novel nanosystem can be extrapolated for active targeting of the receptors that are overexpressed in cancer cells such as EGFR using the targeting characteristics of thiourea-functionalized SiNPs and therefore encourage further investigation and development of anticancer agents specifically exploiting the EGFR inhibitory activity of such nanoparticles.

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Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents

Cited by 251 publications

References 25 publications

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

Synthesis of Diagnostic Silicon Nanoparticles for Targeted Delivery of Thiourea to Epidermal Growth Factor Receptor-Expressing Cancer Cells

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Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents

Cited by 251 publications

References 25 publications

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

Solvent-Free Synthesis and Spectral Correlation of <sup>1</sup><i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-<sup>1</sup><i>H</i>-Pyrazolines

2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophen­yl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

Synthesis of Diagnostic Silicon Nanoparticles for Targeted Delivery of Thiourea to Epidermal Growth Factor Receptor-Expressing Cancer Cells

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2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene