scholarly journals Uses of -diketones for the synthesis of novel heterocyclic compounds and their antitumor evaluations

2020 ◽  
Vol 34 (2) ◽  
pp. 385-405
Author(s):  
R. M. Mohareb ◽  
M. M. Kamel ◽  
Y. R. Milad
Keyword(s):  
Cell Lines ◽  
Ammonium Acetate ◽  
Benzimidazole Derivative ◽  
Ethyl Cyanoacetate ◽  
Pyridine Derivative ◽  
Active Compounds ◽  
Reference Drug ◽  
Thiophene Derivatives ◽  
Active Methylene ◽  
Dihydropyridine Derivatives

The reaction of the 3-oxo-N,3-diphenylpropan-amide (3) with either malononitrile or ethyl cyanoacetate in ammonium acetate gave the 1,2-dihydropyridine derivatives 6a or 6b, respectively. On the other hand, carrying the same reaction in the presence of triethylamine gave the 1,6-dihydropyridine derivatives 7a and 7b, respectively. Moreover, compound 3 reacted with 2-aminoprop-1-ene-1,1,3-tricarbonitrile to give the pyridine derivative 9. Compound 7b reacted with the active methylene derivatives 10a,b and 4a,b to give the naphthyridine derivatives 11a,b and 12a,b; respectively. Compound 3 was also used for the synthesis of thiophene derivatives 13a,b and 16a,b. In addition, the reaction of ethyl benzoylacetate (1) with o-phenylene diamine gave the benzimidazole derivative 18. The reactivity of the latter product towards different reagents was studied to give different products. The cytotoxicity of the newly synthesized products was studied towards some cancer and normal cell lines, in addition toxicity of compounds was measured and docking of the most active compounds was done. Compounds 6b, 7b, 9, 13a, 13b, 16a, 20b, 20c, 24b, 25 and 26b exhibited optimal cytotoxic effect against cancer tested cell lines. These active compounds were evaluated against c-Met kinase using foretinib as the reference drug where all compounds expressed higher activity than the reference drug.                     KEY WORDS: Ethyl benzoylacetate, Pyridine, Benzimidazole, Cytotoxicity   Bull. Chem. Soc. Ethiop. 2020, 34(2), 385-405 DOI: https://dx.doi.org/10.4314/bcse.v34i2.15

Synthesis of 3,5-dicyano-4-phenyl-2,6-bis(4-p-terphenylyl)-1,4-dihydropyridine. An attempt at extending the Hantzsch synthesis

1985 ◽  
Vol 50 (9) ◽  
pp. 1962-1970 ◽  
Author(s):  
Štefan Marchalín ◽  
Josef Kuthan
Keyword(s):  
Molecular Structure ◽  
Acetic Acid ◽  
Ammonium Acetate ◽  
Spectral Characteristics ◽  
Pyridine Derivative ◽  
Hantzsch Synthesis ◽  
Benzylidene Derivative ◽  
Dihydropyridine Derivatives

The 3-oxopropanenitrile IIIc, prepared from 4-acetyl-p-terphenyl (IV) by the sequence IV → V → VI → IIIc, reacts with benzaldehyde and ammonium acetate in acetic acid to give the Hantzsch 1,4-dihydropyridine VIIc and the corresponding pyridine derivative VIIIc. The alternative cyclocondensation of benzylidene derivative IIc and 3-oxopropanenitrile IIIc in the presence of ammonium acetate exclusively gives the pyridine derivative VIIIc. Rate of thermal and oxidative aromatizations of the 1,4-dihydropyridine derivatives, VIIa → VIIc → VIIIa → VIIIc, decreases in the order VIIc > VIIb > VIIa. Mechanism of these transformations and spectral characteristics of compounds VIIc and VIIIc are discussed with regard to their molecular structure.

scholarly journals Reaction of Malononitrile and Ethyl Cyanoacetate: a Novel Synthesis of Polyfunctional Pyridine Derivatives

1985 ◽  
Vol 40 (11) ◽  
pp. 1537-1540 ◽  
Author(s):  
R. M. Mohareb ◽  
S. M. Fahmy
Keyword(s):  
Carbon Disulphide ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Pyridine Derivative ◽  
Pyridine Derivatives ◽  
Novel Synthesis ◽  
Active Methylene

Malononitrile reacts with ethyl cyanoacetate to give a polyfunctional substituted pyridine derivative 5. The latter compound reacts with aniline, hydrazines and aromatic aldehydes to give condensated products. The active methylene of 5 couples with benzenediazonium chloride to give the phenylhydrazone derivative which cyclises readily to give a pyrido[2,3-d]pyridazine deriva­tive. 5 reacts with trichloroacetonitrile, and carbon disulphide to give fused heterocyclic deriva­tives.

Visible Light Assisted Hantzsch Reaction: Synthesis of Polycyclic Dihydropyridines

2019 ◽  
Vol 16 (8) ◽  
pp. 676-682
Author(s):  
Ankusab Noorahmadsab Nadaf ◽  
Kalegowda Shivashankar
Keyword(s):  
Reaction Time ◽  
Light Intensity ◽  
Ammonium Acetate ◽  
Low Cost ◽  
Aromatic Aldehydes ◽  
Light Irradiation ◽  
High Yield ◽  
Short Reaction Time ◽  
Green Protocol ◽  
Dihydropyridine Derivatives

The polycyclic dihydropyridine nucleus represents the heterocyclic system of invaluable core motifs with wide applications in chemical, biological and physical properties. Although this kind of compounds have been extensively synthesized by other groups, the synthesis of these compounds under CFL light intensity were not explored. The synthesis of polycyclic dihydropyridine derivatives were achieved through the reaction of 4-hydroxycoumarin, aromatic aldehydes and ammonium acetate under CFL light irradiation conditions. A series of polycyclic dihydropyridine derivatives were prepared under CFL light irradiation conditions with high yield, short reaction time, ambient condition and without the use of catalyst. The results displayed an efficient method for the synthesis of polycyclic dihydropyridine derivatives. Clean profile, short reaction time, low cost and use of CFL light intensity instead of catalyst making it a genuinely green protocol.

A New Approach for the Synthesis of Some Pyridine and Pyridone Derivatives

1983 ◽  
Vol 38 (12) ◽  
pp. 1690-1694 ◽  
Author(s):  
O. H. Hishmat ◽  
M. M. Y. Zohair ◽  
J. A. A. Miky
Keyword(s):  
Ammonium Acetate ◽  
Ethyl Cyanoacetate ◽  
New Approach

Both visnaginone and khellinone react with malononitrile, ethyl cyanoacetate or cyanoacetamide in presence of ammonium acetate to give substituted furobenzopyrans or furobenzopyridones.However, the reaction of visnaginone and khellinone with aldehydes, and malononitrile in presence of ammonium acetate leads to the formation of the corresponding 2-amino-4,6-disubstituted pyridine 3-carbonitriles. The latter compounds are also obtained by treating the respective chalcones with malononitrile and ammonium acetate.3-Substituted 1,3-diketobutyrates form with malononitrile or with cyanoacetamide and ammonium acetate the 2-amino-4,6-disubstituted pyridine-3-carbonitriles or the 4,6-di-substituted cyanopyridones, respectively

scholarly journals Synthesis, Characterization and Antiproliferative Evaluation of Pt(II) and Pd(II) Complexes with a Thiazine-Pyridine Derivative Ligand

2021 ◽  
Vol 14 (5) ◽  
pp. 395
Author(s):  
Silvia Gutiérrez-Tarriño ◽  
Javier Espino ◽  
Francisco Luna-Giles ◽  
Ana B. Rodríguez ◽  
José A. Pariente ◽  
...  
Keyword(s):  
Cell Lines ◽  
Anticancer Drugs ◽  
Platinum Complexes ◽  
Chemotherapeutic Agents ◽  
Pyridine Derivative ◽  
Cervix Carcinoma ◽  
Multinuclear Complexes ◽  
Histiocytic Lymphoma ◽  
Ovary Adenocarcinoma

Chemical, pharmacological, and clinical research on anticancer coordination complexes has led to noteworthy anticancer drugs such as cisplatin, carboplatin and oxaliplatin. Although these compounds are effective chemotherapeutic agents in the treatment of different tumors, they are associated with high toxicity and numerous side effects. Several studies have shown that the range of platinum complexes with antitumor activity is not limited to structural analogs of cisplatin. Therefore, the development of convenient anticancer drugs that can be effectively used for the treatment of human tumors has become the main goal of most research groups in this field. In this sense, active platinum complexes without NH groups, transplatinum complexes, multinuclear complexes, cationic complexes, and several classes of palladium(II) complexes have emerged. Herein, the synthesis and characterization of two Pt(II) or Pd(II) complexes with PyTz (2-(2-pyridyl)iminotetrahydro-1,3-thiazine), a thiazine derivative ligand, with the formula [MCl2(PyTz)]·C2H6O (M = Pt(II) or Pd(II)) were reported. The potential anticancer ability of both complexes was evaluated in epithelial cervix carcinoma HeLa, human ovary adenocarcinoma SK-OV-3, human histiocytic lymphoma U-937, and human promyelocytic leukemia HL-60 cell lines. Interestingly, the Pt(II) complex showed great cytotoxic potential against all tumor cell lines tested, whereas the Pd(II) complex displayed slight antitumor actions.

Cytotoxicity and Antibacterial Studies of Newly Synthesized Novel Heterocylcic Pyridine Derivative and its Metal Complexes

2021 ◽  
Vol 6 (4) ◽  
pp. 243-249
Author(s):  
B.R. Chaitanya Kumar ◽  
K. Sudhakar Babu ◽  
J. Latha
Keyword(s):  
Metal Complexes ◽  
Cell Lines ◽  
Cancer Cell ◽  
Metal Ion ◽  
Analytical Data ◽  
Cancer Cell Lines ◽  
Diffusion Method ◽  
Pyridine Derivative ◽  
Bacterial Strains ◽  
Physico Chemical

A pyridine derivative 2-((E)-1-(2-hydrazinyl-4-methyl-6-phenyl-pyridine-3-carboyl)ethyl)pyridine-4- carbonitrile (CPHPC) ligand and its 3d-metal(II) complexes has been synthesized (where [M = Co(II), Ni(II) and Cu(II)]. The physico-chemical, analytical data, UV-Vis, FT-IR, 1H NMR and ESR spectrum methods were used to characterize all of the synthesized complexes. Spectral investigations of metal(II) complexes revealed that the metal ion is surrounded by an octahedral geometry. Low conductance values indicated that the metal(II) complexes behave as non-electrolyte. The cytotoxic activity on lung cancer cell lines and hepatic cancer cell lines A549 and HepG2, respectively, with the ligand and their metal complexes were tested with MTT assay. The ligand and its metal complexes were tested for diverse harmful bacterial strains using the agar well diffusion method on Gram-negative bacteria such as Pseudomonas desmolyticum, Escherichia coli and Klebsiella aerogenes, as well as Gram-positive bacteria Staphylococcus aureus.

One Pot Synthesis, Quantum Chemical Stimulation and Anticancer Evaluation of Some New 8-Azacoumarin Derivatives

2021 ◽  
Author(s):  
Sameh Rizk ◽  
Mohamed Megahed ◽  
Monda Badawy ◽  
Mohamed Aly
Keyword(s):  
Liver Cancer ◽  
Cell Lines ◽  
Analytical Data ◽  
Liver Carcinoma ◽  
One Pot ◽  
Reference Drug ◽  
One Pot Synthesis ◽  
Ic50 Value ◽  
Anti Cancer ◽  
Cancer Activity

Abstract New anticancer agents are highly needed to overcome cancer cell resistance. Synthesis of newly pyrazole, derivatives via heterocyclic ring opening of azacoumarin promoted with grinding and ultrasonic reaction conditions. Efficient solvent less one pot synthesis can be well progressed to afford the good yield of new heterocyclic products that were characterized by IR, 1H-NMR, MS and micro-analytical data. Anticancer evaluation for the synthesized compounds exhibited good cytotoxiciy. The anti-liver cancer activity of all compounds was screened in vitro against hepatocellular carcinoma (HCC) cell lines (HepG-2) by viability assay. The synthesized compounds were evaluated for their anticancer activity and found to exhibit promising activities. All new compounds were tested for possible anti-cancer activity against HepG-2 cell lines in comparison to the reference drug doxorubicin (DOX). Compound 8 was the most active against the liver carcinoma cell line (HepG-2) giving promising half-maximal inhibitory concentration (IC50) value of 27.5 ± 1.3 μg/mL, compared with DOX with IC50 value of 0.36 ± 0.02 μg/mL. However it has weak cytotoxic effects against normal rat hepatocytes with 50% cytotoxic concentration (CC50) = 1820.5 µg/ml (= > 500 µg/ml). Compound 8 was selected to be tested in combination with ionizing gamma radiation. Gene expression levels of the cell cycle inhibitor p21 and caspase-3 was quantified. As well as, Oxidative stress was quantified by measuring the concentration of malondialdehyde (MDA), and antioxidant activity of reduced gluthatione (GSH). This study concluded that the new derivative of the azacomarin compound has an effective anti-cancer effect and it was found that using the new compound with ionizing radiation at a dose of 8 Gy improves the effectiveness of the compound on liver cancer cells.

scholarly journals Click Synthesis, Anticancer Activity, and Molecular Docking Investigation of some Functional 1,2,3-triazole Derivatives

2021 ◽  
Vol 12 (6) ◽  
pp. 7633-7667
Keyword(s):  
Cell Cycle ◽  
Molecular Docking ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Antiproliferative Activity ◽  
Cancer Cell Lines ◽  
Reference Drug ◽  
Active Inhibitor ◽  
Triazole Derivatives

1,2,3-triazole skeleton is a privileged building block for the discovery of new promising anticancer agents. In this report, new 1,4-disubstituted 1,2,3-triazoles with the bioisoster triazole moiety were straightforwardly prepared under copper-catalyzed azide-alkyne [3+2] cycloaddition reactions (CuAAC) regime using a variety of both functional organic azides and terminal alkynes. The resulting functional 1,4-disubstituted 1,2,3-triazole compounds were fully characterized and subsequently tested for their antiproliferative activity against four different cancer cell lines. The cytotoxicity tests carried out with these 1,2,3-triazole derivatives show average IC50 values ranging from 15 to 50 µM by comparison with the standard reference drug, namely doxorubicin. The phosphonate 1,2,3-triazole derivative was found to exhibit the best antiproliferative activity among the studied compounds against the HT-1080 cell lines. It was chosen to evaluate its mode of action in these cancer cell lines. The cell cycle study showed that the phosphonate derivative, compound 8, is the most active inhibitor of the cell cycle at the G0/G1 phase, inducing apoptosis independently of Caspase-3 and causing an increase in the mitochondrial membrane potential (ΔΨm) in the HT-1080 cell lines. Molecular docking studies of this phosphonate derivative into the MMP-2 and MMP-9 metalloproteinases receptors demonstrated the relevance of triazole scaffolds and the pendant phosphonate group in establishing -anion, -alkyl and hydrogen bonding type interactions with residual components in the active MMP pocket.

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