Synthesis, Characterization and Antitumor Activity of 4-Ferrocenylpyridine-3, 5-Dicarbonitrile Derivatives and Sodium Polymeric Complexes Containing Carbanionic Ligands

2015 ◽  
Vol 1766 ◽  
pp. 9-17
Author(s):  
E. Klimova ◽  
J. Sánchez ◽  
M. Flores ◽  
S. Cortez ◽  
T. Ramírez ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Human Tumor ◽  
X Ray Diffraction ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Biological Specificity ◽  
Polymeric Complexes ◽  
Mcf 7

ABSTRACTThe reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile in a ROH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles, 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenyl-methyl-3,4-dihydropyridine-3,5-dicarbonitriles and Na+ polymeric complexes: {[Na+(2-ferrocenyl(tetracyano)propenyl)−L]∞ and [Na+(2-amino-3,5-dicyano-4-ferrocenyl-6-pyridyl-dicyanomethyl)−L]∞ where L = ethanol, methanol. Complexes with L = acetonitrile (c), dimethylformamide (d), acetone (e), ethyl acetate (f) were prepared by recrystallization. The structures of the compounds 4b and Na+ polymeric complexes 5c and 6d, e were established by the spectroscopic data and X-ray diffraction analysis. Two compounds 3a and 4a were tested in vitro against six human tumor cell lines U-251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 to assess their in vitro antitumor activity. The results suggest biological specificity towards PC-3, K-562 and HCT-15 cells for compound 3a, and towards PC-3 cell for compound 4a at doses 50 μM, which are lower than Cisplatin IC50′s in the three cell lines.

Reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile: formation of 4-ferrocenylpyridine-3,5-dicarbonitrile derivatives and sodium polymeric complexes containing carbanionic ligands

2014 ◽  
Vol 86 (11) ◽  
pp. 1839-1852 ◽  
Author(s):  
Elena Ivanovna Klimova ◽  
Marcos Martínez García ◽  
Jessica Jazmin Sánchez García ◽  
Teresa Ramírez Apan ◽  
Andrei V. Churakov ◽  
...  
Keyword(s):  
Human Tumor ◽  
Tumor Cell Lines ◽  
X Ray Diffraction ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
X Ray ◽  
Biological Specificity ◽  
Polymeric Complexes ◽  
Mcf 7

Abstract The reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile in a EtOH/H2O or MeOH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles 3a,b (multi-component condensation), 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles 4a,b (multi-component cyclodimerization) and Na+ polymeric complexes: {[Na+(2-ferrocenyl(tetracyano)propenyl)–L]∞5a,b and [Na+(2-amino-3,5-dicyano-4-ferrocenyl-6-pyridyl-dicyanomethyl)–L]∞6a,b, where L = ethanol, methanol. Complexes with L = acetonitrile, dimethylformamide, acetone, ethyl acetate were prepared by recrystallization. The structures of the compounds 3b, 4b and Na+ polymeric complexes were established by the spectroscopic data and X-ray diffraction analysis. Two compounds 3a and 4a were tested in vitro against six human tumor cell lines U-251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 to assess their in vitro antitumor activity. The results suggest biological specificity towards PC-3, K-562 and HCT-15 cells for compound 3a, and towards PC-3 cell for compound 4a at doses of 50 μM, which are lower than cis-platin.

scholarly journals Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

Rodriguésia ◽  
2020 ◽  
Vol 71 ◽  
Author(s):  
Fernando Duarte Cabral ◽  
Cassia Cristina Fernandes ◽  
Arthur Barcelos Ribeiro ◽  
Iara Squarisi Squarisi ◽  
Denise Crispim Tavares ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Normal Cell ◽  
Human Tumor ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Ic50 Values ◽  
Mcf 7

Abstract This paper aims to investigate, for the first time, in vitro antitubercular, antileishmanial and antiproliferative activities of essential oils (EOs) from S. odoratissima leaves and flowers - grown in midwestern Brazil - against Mycobacterium tuberculosis, promastigote forms of Leishmania amazonensis and human tumor cell lines. Antimycobacterial activity of EOs was evaluated in terms of the minimal inhibitory concentration (MIC). EOs from leaves and flowers showed to be active antimicrobials against M. tuberculosis, since MIC values were 150 µg/mL and 162.5 µg/mL, respectively. Both EOs exhibited significant activity against promastigote forms of L. amazonensis; IC50 values (50% growth inhibition) were 14.36 ± 2.02 (EOs from leaves) and 19.89 ± 2.66 µg/mL (EOs from flowers). Antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumor (MCF-7, HeLa and M059J) cell lines was performed by the XTT assay; results were expressed as IC50 (50% cell growth inhibition) and the selective index was calculated. IC50 values of EOs from leaves and flowers obtained in normal cell lines for were 502.97 ± 40.33 µg/mL and 370.60 ± 2.01 µg/mL, respectively. Antiproliferative activity was observed against human tumor cell lines, whose IC50 values were significantly lower than those obtained in normal cell lines of MCF-7 cells (367.57 ± 4.46 µg/mL-EOs from leaves and 357.70 ± 1.85 µg/mL-EOs from flowers) and M059J cells (492.53 ± 56.67 µg/mL-EOs from leaves and 324.90 ± 6.72 µg/mL-EOs from flowers), thus, indicating selectivity. These in vitro results showed that EOs from S. odoratissima may be an antimycobacterial, antiparasitic and antitumor agent.

scholarly journals New Cytotoxic Cycloartane Triterpenes from the Aerial Parts of Actaea heracleifolia (syn. Cimicifuga heracleifolia)

Planta Medica ◽  
2018 ◽  
Vol 85 (02) ◽  
pp. 154-159
Author(s):  
Qiang-Qiang Shi ◽  
Wei-Hua Wang ◽  
Jing Lu ◽  
Da-Shan Li ◽  
Lin Zhou ◽  
...  
Keyword(s):  
Cell Lines ◽  
Human Tumor ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Chemical Structures ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Weak Activity ◽  
Mcf 7

AbstractOne new 15,16-seco-cycloartane triterpene (1), three new cycloartane triterpene glycosides (2–4), and five known compounds (5–9) were isolated from the aerial parts of Actaea heracleifolia. The chemical structures of these compounds were determined on the basis of NMR analysis, HRTOF-ESIMS data, and other spectroscopic methods. Selected compounds were evaluated for their cytotoxicity against human tumor cell lines (HL-60, SMMC-7721, A549, MCF-7, and SW480) in vitro. Compounds 3 and 4 showed weak activity against the HL-60, A-549, and MCF-7 cell lines with IC50 values ranging from 21.34 to 36.98 µM.

scholarly journals Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis

2020 ◽  
Vol 70 (2) ◽  
pp. 161-178 ◽  
Author(s):  
Yaser A. El-Badry ◽  
Mahr A. El-Hashash ◽  
Khalil Al-Ali
Keyword(s):  
Antitumor Activity ◽  
Cell Lines ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Human Tumor ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Solvent Free Conditions ◽  
Modest Activity

AbstractA series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H) -yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c).

Synthesis and Cytotoxicity of New Mannich Bases of 6-[3-(3,4,5-Trimetoxyphenyl)-2- propenoyl]-2(3H)-Benzoxazolone

2020 ◽  
Vol 17 (4) ◽  
pp. 512-517
Author(s):  
Ognyan Ivanov Petrov ◽  
Yordanka Borisova Ivanova ◽  
Mariana Stefanova Gerova ◽  
Georgi Tsvetanov Momekov
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Biological Activities ◽  
Human Tumor ◽  
Mannich Bases ◽  
In Vitro Cytotoxicity ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines

Background: Chemotherapy is one of the mainstays of cancer treatment, despite the serious side effects of the clinically available anticancer drugs. In recent years increasing attention has been directed towards novel agents with improved efficacy and selectivity. Compounds with chalcone backbone have been reported to possess various biological activities such as anticancer, antimicrobial, anti-inflammatory, analgesic, antioxidant, etc. It was reported that aminomethylation of hydroxy chalcones to the corresponding Mannich bases increased their cytotoxicity. In this context, our interest has been focused on the design and synthesis of the so-called multi-target molecules, containing two or more pharmacophore fragments. Methods: A series of Mannich bases were synthesized by the reaction between 6-[3-(3,4,5- trimethoxyphenyl)-2-propenoyl]-2(3Н)-benzoxazolone, formaldehyde, and a secondary amine. The structures of the compounds were confirmed by elemental analysis, IR and NMR spectra. The new Mannich bases were evaluated for their in vitro cytotoxicity against a panel of human tumor cell lines, including BV-173, SKW-3, K-562, HL-60, HD-MY-Z and MDA-MB-231. The effects of selected compounds on the cellular levels of glutathione (GSH) were determined. Results: The new compounds 4a-e exhibited concentration-dependent cytotoxic effects at micromolar concentrations in MTT-dye reduction assay against a panel of human tumor cell lines, similar to those of starting chalcone 3. The tested agents led to concentration - dependent depletion of cellular GSH levels, whereby the effects of the chalcone prototype 3 and its Mannich base-derivatives were comparable. Conclusion: The highest chemosensitivity to the tested compounds was observed in BV- 173followed by SKW-3 and HL-60 cell lines.

scholarly journals Pharmacoinformatics and Preclinical Studies of NSC765690 and NSC765599, Potential STAT3/CDK2/4/6 Inhibitors with Antitumor Activities against NCI60 Human Tumor Cell Lines

Biomedicines ◽  
2021 ◽  
Vol 9 (1) ◽  
pp. 92
Author(s):  
Bashir Lawal ◽  
Yen-Lin Liu ◽  
Ntlotlang Mokgautsi ◽  
Harshita Khedkar ◽  
Maryam Rachmawati Sumitra ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Cancer Cell ◽  
Human Tumor ◽  
Cancer Cell Lines ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Anti Cancer

Signal transducer and activator of transcription 3 (STAT3) is a transcriptional regulator of a number of biological processes including cell differentiation, proliferation, survival, and angiogenesis, while cyclin-dependent kinases (CDKs) are a critical regulator of cell cycle progression. These proteins appear to play central roles in angiogenesis and cell survival and are widely implicated in tumor progression. In this study, we used the well-characterized US National Cancer Institute 60 (NCI60) human tumor cell lines to screen the in vitro anti-cancer activities of our novel small molecule derivatives (NSC765690 and NSC765599) of salicylanilide. Furthermore, we used the DTP-COMPARE algorithm and in silico drug target prediction to identify the potential molecular targets, and finally, we used molecular docking to assess the interaction between the compounds and prominent potential targets. We found that NSC765690 and NSC765599 exhibited an anti-proliferative effect against the 60 panels of NCI human cancer cell lines, and dose-dependent cytotoxic preference for NSCLC, melanoma, renal, and breast cancer cell lines. Protein–ligand interactions studies revealed that NSC765690 and NSC765599 were favored ligands for STAT3/CDK2/4/6. Moreover, cyclization of the salicylanilide core scaffold of NSC765690 mediated its higher anti-cancer activities and had greater potential to interact with STAT3/CDK2/4/6 than did NSC765599 with an open-ring structure. NSC765690 and NSC765599 met the required safety and criteria of a good drug candidate, and are thus worthy of further in-vitro and in-vivo investigations in tumor-bearing mice to assess their full therapeutic efficacy.

Synthesis and Characterization of New Palladium(II) Complexes with Ligands Derived from Furan-2-carbaldehyde and Benzaldehyde Thiosemicarbazone and their in vitro Cytotoxic Activities against Various Human Tumor Cell Lines

2010 ◽  
Vol 65 (10) ◽  
pp. 1271-1278 ◽  
Author(s):  
Wilfredo Hernández ◽  
Juan Paz ◽  
Fernando Carrasco ◽  
Abraham Vaisberg ◽  
Jorge Manzur ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Human Tumor ◽  
Myelogenous Leukemia ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines

With the ligands 4-phenyl-1-(furan-2-carbaldehyde)thiosemicarbazone, HTSC1, (1), 4-phenyl-1- (5´-phenyl-furan-2-carbaldehyde)thiosemicarbazone, HTSC2 (2), o-methoxy-benzaldehydethiosemicarbazone, HTSC3 (3), and o-cyano-benzaldehydethiosemicarbazone, HTSC4 (4), the corresponding palladium(II) complexes, Pd(TSC1)2 (5), Pd(TSC2)2 (6), Pd(TSC3)2 (7), and Pd(TSC4)2 (8) were synthesized and characterized by elemental analysis and spectroscopic techniques. The crystal structure of Pd(TSC3)2 (7) was determined by single-crystal X-ray diffraction. Complex 7 shows a squareplanar geometry, where two deprotonated ligands are coordinated to the PdII center through the nitrogen and sulfur atoms in a trans arrangement. In vitro antitumor studies against different human tumor cell lines have revealed that the palladium(II) complexes 5- 8 are more cytotoxic (IC50 values in the range of 0.21 - 3.79 μM) than their corresponding ligands (1 - 4) (> 60 μM). These results indicate that the antiproliferative activity is enhanced when thiosemicarbazone ligands are coordinated to the metal. Among the studied palladium(II) complexes, 8 exhibits high antitumor activity on K562 chronic myelogenous leukemia cells with a low value of the inhibitory concentration (IC50 = 0.21 μM).

scholarly journals Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study

2020 ◽  
Vol 18 (1) ◽  
pp. 453-462
Author(s):  
Jerry O. Adeyemi ◽  
Damian C. Onwudiwe ◽  
Nirasha Nundkumar ◽  
Moganavelli Singh
Keyword(s):  
Cell Lines ◽  
Human Tumor ◽  
Complexation Reaction ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
Human Tumor Cell Lines ◽  
H Nmr ◽  
Cytotoxicity Studies ◽  
Final Residue ◽  
Mcf 7

AbstractAmmonium benzyldithiocarbamate, represented as NH4L, was prepared and used in the complexation reaction involving three organotin(iv) salts, represented as R2SnCl2 (R = CH3, C4H9, and C6H5). The structures of the synthesized complexes [(CH3)2SnL2] (1), [(C4H9)2SnL2] (2), and [(C6H5)2SnL2] (3) were established using various spectroscopic techniques (Fourier transform infrared spectroscopy, 1H NMR, 13C NMR, and 119Sn NMR) and elemental analysis. Thermal decomposition of the complexes using thermogravimetric analysis under nitrogen showed no definite pathway in the pattern of the complexes even though they are structurally related. X-ray diffraction studies of the final residue showed a common diffraction pattern for the complexes and confirmed SnS as the product of the thermal treatment. Cytotoxicity studies of these complexes against the human tumor cell lines (HeLa and MCF-7) compared favorably with the used standard 5-fluorouracil drug, with complexes 2 and 3 showing very good activity toward the used cell lines.

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