Methylation of 4-nitro-3(5)-pyrazolecarboxylic acid

Regiec, Andrzej; Mastalarz, Henryk; Mastalarz, Agnieszka; Kochel, Andrzej

doi:10.1016/j.tetlet.2009.02.223

Cited by 13 publications

(9 citation statements)

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“…In order to obtain the desired nitropyrazole complexes ( Figure 3 ), we synthesized six nitro 1-methylpyrazole derivatives, namely 1-methyl-3-nitropyrazole [ 32 ], 1-methyl-4-nitropyrazole [ 33 ], 1-methyl-5-nitropyrazole [ 32 ], 1,3-dimethyl-4-nitropyrazole [ 41 ], methyl 1-methyl-4-nitropyrazole-5-carboxylate [ 42 ] and methyl 1-methyl-4-nitropyrazole-3-carboxylate, according to the previously described procedures [ 42 ]. Using 1-methylated ligands allowed us to avoid the troublesome formation of additional isomers caused by the ring N–H tautomerism and should enhance the bioavailability of synthesized Pt complexes due to higher lipophilicity.…”

Section: Resultsmentioning

confidence: 99%

“…A solution of 254 mg (2 mmol) of 1-methyl-4-nitropyrazole [ 33 , 42 ] in 15 mL of warm water was mixed with a solution of 415 mg (1 mmol) of K 2 PtCl 4 in 5 mL of water. The reaction mixture was maintained in darkness at 25 °C and monitored periodically by TLC until the absence of free ligand (app.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of 370 mg (2 mmol) of methyl 1-methyl-4-nitropyrazole-5-carboxylate [ 42 ] in 7 mL of acetone was mixed with a solution of 415 mg (1 mmol) of K 2 PtCl 4 in 10 mL of water and maintained in darkness at 25 °C for 1 month. The resulting yellow precipitate was filtered off and washed with chloroform to remove unchanged starting material, giving 500 mg of crude product which mainly consisted of two individual Pt compounds (TLC).…”

Section: Methodsmentioning

confidence: 99%

“…A solution of 170 mg (0.92 mmol) of methyl 1-methyl-4-nitropyrazole-3-carboxylate [ 42 ] in 6 mL of acetone was mixed with a solution of 190 mg (0.46 mmol) of K 2 PtCl 4 in 10 mL of water and maintained in darkness at 25 °C for 1 month. The resulting precipitate consisting mostly of unchanged starting material was filtered off and the filtrate was evaporated to dryness and extracted with acetone giving, after evaporation, 190 mg of solid residue.…”

Section: Methodsmentioning

confidence: 99%

“…ESI MS (negative ionization) of 3 and 4 revealed, amongst others, the following peak given as a ratio m/z [u/e]: 517.9555 [PtL 2Cl 2 -H] --quasi-molecular ion peak, where L = 1-methyl-5-nitropyrazole.5.2.5. Complexation with Methyl 1-Methyl-4-Nitropyrazole-5-CarboxylateA solution of 370 mg (2 mmol) of methyl 1-methyl-4-nitropyrazole-5-carboxylate[42] in 7 mL of acetone was mixed with a solution of 415 mg (1 mmol) of K 2 PtCl 4 in 10 mL of water and maintained in darkness at 25 • C for 1 month. The resulting yellow precipitate was filtered off and washed with chloroform to remove unchanged starting material, giving 500 mg of crude product which mainly consisted of two individual Pt compounds (TLC).These compounds were separated and purified using column chromatography on SiO 2 with chloroform-acetone mixture as eluent, giving 170 mg (27%) of cis-dichloridobis(methyl 1-methyl-4-nitropyrazole-5-carboxylate)platinum(II) (5, less polar fraction) and 50 mg (8%) of trans-dichloridobis(methyl 1-methyl-4-nitropyrazole-5-carboxylate)platinum(II)(6).…”

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Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity

Mastalarz

Wietrzyk

et al. 2020

Pharmaceuticals

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A series of eight novel platinum(II) complexes were synthesized by the reaction of the appropriate 1-methylnitropyrazole derivatives with K2PtCl4 and characterized by elemental analysis, ESI MS spectrometry, 1H NMR, 195Pt NMR, IR and far IR spectroscopy. Thermal isomerization of cis-dichloridobis(1-methyl-4-nitropyrazole)platinum(II) 1 to trans-dichloridobis(1-methyl-4-nitropyrazole)platinum(II) 2 has been presented, and the structure of the compound 2 has been confirmed by X-ray diffraction method. Cytotoxicity of the investigated compounds was examined in vitro on three human cancer cell lines (MCF-7 breast, ES-2 ovarian and A-549 lung adenocarcinomas) and their logP was measured using a shake-flask method. The trans complex 2 showed better antiproliferative activity than cisplatin for all the tested cancer cell lines. Additionally, trans-dichloridobis(1-methyl-5-nitropyrazole)platinum(II) 4 has featured a lower IC50 value than reference cisplatin against MCF-7 cell line. To gain additional information that may facilitate the explanation of the mode of action of tested compounds cellular platinum uptake, stability in L-glutathione solution, influence on cell cycle progression of HL-60 cells and ability to apoptosis induction were determined for compounds 1 and 2.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity

Mastalarz

Wietrzyk

et al. 2020

Pharmaceuticals

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Synthesis and characterization of copper, nickel, cobalt, zinc complexes with 4-nitro-3-pyrazolecarboxylic acid ligand

Jaćimović

Kosović

Kastratović

et al. 2018

J Therm Anal Calorim

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In the continuation of our systematic research of pyrazole coordination compounds, complexes of Cu(II), Ni(II), Co(II) and Zn(II) with 4-nitro-3-pyrazolecarboxylic acid ligand (L) were synthesized in the reaction of warm ethanolic solutions of the ligand and CuCl 2 Á2H 2 O, Ni(CH 3 COO) 2 , CoCl 2 Á6H 2 O and Zn(CH 3 COO) 2 , mixed in the metal-to-ligand ratio of 1:2. As the compounds could not be obtained in the form suitable for single-crystal structure analysis, their bis(ligand) structures, ML 2 (M = Cu II , Ni II , Co II and Zn II ) were proposed on the basis of elemental analysis, IR spectrometry, conductometric and TG-MS measurements. The low conductivity of the compounds additionally supports the deprotonation of the ligand and the formation of neutral complexes. The solvent content was calculated using the thermogravimetric (TG) data. According to TG data, the copper(II) compound crystallizes with 8 while nickel(II) complex with 4 water molecules, CuL 2 Á8H 2 O, NiL 2 Á4H 2 O. Complexes of Co(II) and Zn(II) contain 1 and 1.5 water molecules. Despite the differences in solvation properties, the high similarity in the course of the decomposition refers to the similar coordination mode of the organic ligand. The crystal and molecular structures of HLÁH 2 O and NH 4 [LHL] were determined by single-crystal X-ray structure analysis. Biological research based on determining the inhibition effect of commercial fungicide Cabrio top, ligand, and all newly synthesized complexes on Ph. viticola has been carried out using the phytosanitary method.

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Pyrazoles

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2022

Comprehensive Heterocyclic Chemistry IV

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Methylation of 4-nitro-3(5)-pyrazolecarboxylic acid

Cited by 13 publications

References 4 publications

Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity

Synthesis of Platinum(II) Complexes with Some 1-Methylnitropyrazoles and In Vitro Research on Their Cytotoxic Activity

Synthesis and characterization of copper, nickel, cobalt, zinc complexes with 4-nitro-3-pyrazolecarboxylic acid ligand

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