pyrazoles-derivatives

Synthesis and antimicrobial activity of 2-(1H-pyrazol-4-yl)-1H-benzo[d]imidazole derivatives was written by Bhavanarushi, S.;Gandu, Bharath;Gangagnirao, A.;Vatsala, Rani J.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2014.Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one This article mentions the following:

A series of novel 2-(1H-pyrazol-4-yl)-1H-benzo[d]imidazole derivatives were prepared and tested in vitro for their antimicrobial activity against three gram pos. bacteria like Bacillus licheniformis, Bacillus subtilis and Staphylococcus aureus three Gram neg. bacteria like Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa and four fungal strains like Aspergillus niger, Candida albicans, Fusarium oxysporum and Fusarium solani. The min. inhibitory concentrations (MICs) of some of the synthesized compounds showed high antibacterial and antifungal activities at low concentrations (6.25-200 μg/mL), with respect to reference drug. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Recommanded Product: 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Liquefaction of giant fennel (Ferula orientalis L.) in supercritical organic solvents: Effects of liquefaction parameters on product yields and character was written by Aysu, Tevfik;Kucuk, Mehmet Masuk. And the article was included in Journal of Supercritical Fluids in 2013.Electric Literature of C5H9N3 This article mentions the following:

Ferula orientalis L. stalks were liquefied in an autoclave in supercritical organic solvents (methanol, ethanol, 2-propanol, acetone and 2-butanol) with (NaOH, Na₂CO₃, ZnCl₂) and without catalyst at five different temperatures ranging from 240°C to 320°C. The amounts of solid (unconverted raw material), liquid (bio-oil) and gas produced, as well as the composition of the resulting liquid phase, were determined The effects of various parameters such as temperature, solvent, catalyst and ratio of catalyst on product yields were investigated. The results showed that conversion highly depends on the temperature and catalyst. The highest bio-oil yield (53.97%) was obtained using acetone with 10% zinc chloride at 300°C. The liquid products were extracted with benzene and di-Et ether. Some of selected liquid products (bio-oils) were analyzed by elemental, FT-IR and GC-MS. 126 different compounds were identified by GC-MS in the liquid products obtained in ethanol at 300°C. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Electric Literature of C5H9N3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Electric Literature of C5H9N3

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Versatile synthesis of 6-alkyl(aryl)-1H-pyrazolo[3,4-d]pyrimidin-4[5H]-ones was written by Reddy, K. Hemender;Reddy, A. Panduranga;Veeranagaiah, V.. And the article was included in Indian Journal of Chemistry in 1992.Computed Properties of C5H8N4O This article mentions the following:

Condensation of 5-amino-1H-pyrazole-4-carboxamide (I, R = H) with various aromatic aldehydes furnishes 6-substituted 1H-pyrazole[3,4-d]pyrimidin-4(5H)-ones II (R¹ = Ph, substituted Ph) via the intermediate 5-(N-arylideneamino)pyrazole-4-carboxamides. II were also synthesized by the reaction of I (R = H) with aromatic carboxylic acids in polyphosphoric acid (PPA) or polyphosphate ester (PPE). Similar treatment of I (R = Ph, Me) with aromatic aldehydes and aromatic carboxylic acids gives exclusively 6-substituted 1-methyl/phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones. The title compounds have were also synthesized by the reaction of I with arylideneanilines. In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7Computed Properties of C5H8N4O).

5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7) belongs to pyrazole derivatives. Pyrazoles, a five-membered heterocycle containing two adjacent nitrogen atoms, are the core structures found in a number of molecules that possess a wide range of pharmaceutical and agricultural activities. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Computed Properties of C5H8N4O

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Compounds containing the trifluoromethyl group was written by Gilman, H.;Tolman, L.;Yeoman, F.;Woods, L. A.;Shirley, D. A.;Avakian, S.. And the article was included in Journal of the American Chemical Society in 1946.Formula: C4H3F3N2O This article mentions the following:

The following compounds were prepared as possible antimalarials. Of the compounds tested only m-(trifluoromethyl)benzenearsonic acid (I) showed activity but the specific contribution of the F₃C group to such action is uncertain. m-F₃CC₆H₄N₂Cl (0.0163 mole), added to a cold solution of 0.0163 mole of 2-hydroxydibenzofuran in KOH (temperature below 5°) with stirring for 30 min., give 46-50% of 1-(m-trifluoromethylphenylazo)-2-hydroxydibenzofuran, red, m. 173-4°; 2,8-dihydroxydibenzofuran gives 15-20% of the 2,5-di-HO derivative, orange-brown, m. 256-7°. m-F₃CC₅H₄Br (Simons and Ramler, C.A. 37, 2341.8) has n_D²⁰ 1.4749, d₂₇²⁹ 1.606 (55% yield); the Grignard reagent yields 52-9% of m-(trifluoromethyl)benzaldehyde (II), b₁₀ 64-6°, n_D²⁰ 1.4660, d₂₇²⁹ 1.300; 2,4-dinitrophenylhydrazone, yellow, m. 259-60°. II (5.48 g.) and 5.3 g. m-F₃CC₆H₄NH₂ in 50 cc. C₆H₆, refluxed 5 hrs., give 62% of N-(m-trifluoromethylbenzylidene)-m-(trifluoromethyl)aniline, m. 50-1°. II yields 65% of an oxime, b₁₂ 102-4°, n_D²⁰ 1.5128, d₂₇²⁹ 1.305. p-H₂NC₆H₄NHAc (25 g.) and 19 g. (CH₂Ac)₂, heated on the steam bath for 1 hr., give 73% of N-(p-acetamidophenyl)-2,5-dimethylpyrrole, m. 207-8°. 4-Dibenzofuraldehyde yields a 2,4-dinitrophenylhydrazone, yellow, m. 301-2°. II (0.95 g.) and 1 g. 4-aminodibenzofuran in C₆H₆, refluxed 1 hr. and the residual red oil heated at 120-30° for 1 hr., give 29% of 4-(m-trifluoromethylbenzylideneamino)dibenzofuran, m. 81-3°. m-F₃CC₆H₄NH₂ (10 g.), 11.5 g. Et₂N(CH₂)₃Cl, and a trace of Cu, heated 5 hrs. at 135-40°, give 27% of m-(3-diethylaminopropylamino)(trifluoromethyl)benzene, light yellow, b₂₃ 171-5°. m- F₃CC₆H₄N₂Cl yields 51% of I, m. 137-8°. 3,6-H₂N(O₂N)C₆H₃CF₃ (Rouche, C.A. 22, 2149) (41 g.), 29 g. H₃AsO₃, and 53 g. C₃H₅(OH)₃, added to 56 g. concentrated H₂SO₄, stirred 2 hrs., and refluxed 2 hrs., give 56% of 6-nitro-7-(trifluoromethyl)quinoline, m. 164-5°; reduction with SnCl₂-concentrated HCl gives 92% of the 6-NH₂ derivative (III), m. 154-5°. III (5 g.) and (CH₂Ac)₂ in 10 cc. EtOH and 1 drop concentrated HCl, refluxed 22 hrs., give 46% of 6-(2,5-dimethylpyrryl)-7-(trifluoromethyl)quinoline, b₁ 135-8°, m. 86-7°. F₃CCH₂COCH₂CO₂Et (10 g.) and 2.6 cc. N₂H₄.H₂O in 20 cc. hot H₂O give 46.3% of 3-trifluoromethyl-5-pyrazolone, m. 208.5-9.2°. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Formula: C4H3F3N2O).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. Formula: C4H3F3N2O

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Heterocycle synthesis through reactions of nucleophiles with acrylonitriles. 12. A new route for the synthesis of pyrano[3,2-d]pyrimidines and pyrano[2,3-c]pyrazoles was written by Abdel-Latif, Fathy Fahim. And the article was included in Indian Journal of Chemistry in 1991.HPLC of Formula: 51395-52-9 This article mentions the following:

A new route for the synthesis of pyranopyrimidines I (X = O, S; Ar = Ph, 2-furyl, 2-thienyl, 4-pyridyl) through the reaction of barbituric acid or thiobarbituric acid with ArCH:CRR¹ (II; R = CN; R¹ = CO₂Et) is reported. A similar reaction of II (R = R¹ = CN) gave ylidenes III. The reaction of bromomethylpyrazolinone IV with II (Ar = 2-thienyl; R = R¹ = CN) gave pyranopyrazole V. In the experiment, the researchers used many compounds, for example, 4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9HPLC of Formula: 51395-52-9).

4-Bromo-3-methyl-1H-pyrazol-5(4H)-one (cas: 51395-52-9) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 °C).Pyrazole used as a ligand to prepare organometallic compounds. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.HPLC of Formula: 51395-52-9

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthesis and pharmacological activity of N-hetaryl-3(5)-nitropyridines was written by Klimenko, A. I.;Divaeva, L. N.;Zubenko, A. A.;Morkovnik, A. S.;Fetisov, L. N.;Bodryakov, A. N.. And the article was included in Russian Journal of Bioorganic Chemistry in 2015.Application In Synthesis of 4-Chloro-3,5-dimethyl-1H-pyrazole This article mentions the following:

Previously undescribed 2-, 4 or 6-substituted hetaryl-3(5)-nitropyridines were synthesized by the interaction of a number of chloro-substituted 3(5)-nitropyridines with some diazoles or 3-chloropyridazin-6-one. In addition, pyrazolyl-3-nitropyridines were prepared by both the above method and cyclization of hydrazinopyridines, which, in turn, were synthesized by the treatment of chloro-substituted 3-nitropyridines with hydrazine. It has been shown that these compounds have a moderate antibacterial activity against some pathogenic gram-pos. and gram-neg. bacteria (Staphylococcus aureus and Escherichia coli) and a strong protistocidal effect on protozoa species Colpoda steinii surpassing in this respect clin. used reference drugs. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Application In Synthesis of 4-Chloro-3,5-dimethyl-1H-pyrazole).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. The 1H-pyrazole provides an excellent means by which to provide the requisite hydrogen bond acceptor–donor motifs, whether as a monocyclic ring or as a fused indazole ring. The presence of both electronegative nitrogen atoms in the pyrazole ring reduces the electron density of the C3- and C5-positions leaving electron density of C4-position unaltered. Thus the C4-position is vulnerable to electrophilic attack. The C3 electrophilic-position may undergo deprotonation in the presence of a strong base leading to ring opening.Application In Synthesis of 4-Chloro-3,5-dimethyl-1H-pyrazole

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Modulating Supramolecular Reactivity Using Covalent “Switches” on a Pyrazole Platform was written by Aakeroy, Christer B.;Hurley, Evan P.;Desper, John. And the article was included in Crystal Growth & Design in 2012.SDS of cas: 15953-73-8 This article mentions the following:

Systematic co-crystallizations of halogen-, methyl-, and nitro-substituted pyrazoles with a library of 20 aromatic carboxylic acids have been carried out using melt and solution-based experiments The solids resulting from all reactions were screened using IR spectroscopy in order to determine if a reaction (co-crystal or salt) had taken place. The halogenated pyrazoles, including their di-Me analogs, gave a supramol. yield of 55-70%. Replacing a halogen atom (R-X, X = Cl, Br, I) with a nitro (R-NO₂) group drops the success rate significantly to 10% due to the reduced charge on the basic nitrogen atom of the pyrazole. Eleven crystal structures were obtained: six were co-crystals and five were salts (including one hydrate). In all six co-crystals, dimeric pyrazole···acid assemblies were constructed via a combination of O-H···N(pyz) and N-H···O hydrogen bonds corresponding to a 100% supramol. yield. A variety of weaker halogen-bonds CN···I, I···I and X···O^– connect dimers into infinite one-dimensional chains. In contrast, the salts displayed a variety of stoichiometries and a much wider range of noncovalent interactions, although a charge-assisted N⁺-H···O^– hydrogen bond was present in all five structures. In general, the salts lack structural and stoichiometric predictability and stability as compared to the co-crystals. Furthermore, the overall electrostatic charge on the key binding sites on the pyrazole backbone can be modulated by using specific covalent switches, which in turn can increase (or decrease) the success rate for a reaction. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8SDS of cas: 15953-73-8).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazole the presence of this nucleus in pharmacological agents of diverse therapeutic categories such as celecoxib, a potent anti-inflammatory, the antidepressant agent fezolamide have proved the pharmacological potential of the pyrazole moiety. SDS of cas: 15953-73-8

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthesis of substituted 6-amino-4-aryl-5-cyano-2H,4H-pyrano[2,3-c]pyrazoles. Crystal and molecular structure of 6-amino-5-cyano-3-methyl-4-(2′,4′,6′-triethylphenyl)-2H,4H-pyrano[2,3-c]pyrazole was written by Shestopalov, A. M.;Yakubov, A. P.;Tsyganov, D. V.;Emel’yanova, Yu. M.;Nesterov, V. N.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii) in 2002.Synthetic Route of C4H3F3N2O This article mentions the following:

Substituted 6-aminopyrano[2,3-c]pyrazoles I [R = Me, Et, n-Pr, tert-Bu, Ph, CF₃, MeOCH₂, MeOCOCH₂, 4-MeC₆H₄SCH₂; R¹ = 2,4,6-Me₃C₆H₂, 2,4,6-Me₃-3-O₂NC₆H, 2,4,6-Me₃-3,5-(O₂N)₂C₆, 2,4,6-Me₃-3-(EtOCH₂)C₆H, 2,4,6-Et₃C₆H₂, 2,5-(MeO)₂C₆H₃, 2,3,4-, 2,4,5-(MeO)₃C₆H₂, 2-F₃C-, 2-MeC₆H₄, 2-(2-ClC₆H₄CH₂O)C₆H₄, 2-thienyl, 2-furanyl, 3-pyridinyl] were synthesized by the two-component condensation of arylidenemalononitriles, R¹CH:C(CN)₂, and pyrazolones II or by the three-component condensation of aromatic aldehydes, R¹CHO, malononitrile, and pyrazolones II. It was established by X-ray crystallog. anal. that pyranopyrazoles exist in the 2H and not the 1H tautomeric form. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Synthetic Route of C4H3F3N2O).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. Pyrazoles and pyrimidines have diverse biological and pharmacological activities. There are a number of antimicrobial compounds containing pyrazole moiety as the core unit. Pyrazofurin is important antimicrobial drug and 2-methylpyrimidine-4-ylamine derivatives I and II were found to be effective inhibitors of Escherichia coli PDHc-E1 with antibacterial and antifungal activity.Synthetic Route of C4H3F3N2O

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

N-(2-Fluoro-2,2-dinitroethyl)azoles: a novel assembly of diverse explosophoric building blocks for energetic compound design was written by Palysaeva, Nadezhda V.;Gladyshkin, Aleksei G.;Vatsadze, Irina A.;Suponitsky, Kyrill Yu.;Dmitriev, Dmitry E.;Sheremetev, Aleksei B.. And the article was included in Organic Chemistry Frontiers in 2019.Recommanded Product: 5334-39-4 This article mentions the following:

The first simple two-step protocol to efficiently prepare unprecedented N-(2-fluoro-2,2,-dinitroethyl) derivatives of imidazoles, pyrazoles, triazoles and tetrazoles e.g., I. Michael addition of NH-azoles to 1,1-dinitroethene, generated from 1,1,1-trinitroethane, followed by fluorination provided the N-dinitrofluoroethylated nitrogen heterocycles in moderate to good overall yields. The synthesis employed azoles with electron-withdrawing groups, predominantly the nitro group and could be extended to other structurally attractive electron-deficient NH-heterocycles. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Recommanded Product: 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazole rings have been used as core components of several leading non-steroidal anti-inflammatory drugs (NSAIDs) and antihypertensive drugs. It has also been found to be useful as a bifunctional ligand for metal catalysis.Recommanded Product: 5334-39-4

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthesis and structure-activity relationships of quaternary ammonium cephalosporins with 3-pyrazolylpyridinium derivatives was written by Chang, Kwan Young;Kim, Sung Hoon;Nam, Ghilsoo;Seo, Jae Hong;Kim, Joong Hyup;Ha, Deok-Chan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2000.Reference of 45887-08-9 This article mentions the following:

Cephalosporins with 3-pyrazolylpyridinium at C-3 position, which is supposed to exhibit synergic activity of ceftazidime and cefoselis, were synthesized and their antibacterial activity against Gram-pos. and Gram-neg. was inspected. In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Reference of 45887-08-9).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. As is the case with imidazoles, the pyrazole ring offers many opportunities to create new multiring systems that incorporate this heterocycle. The pyrazole ring is resistant to oxidation and reduction but the groups, such as alkyl and formyl attached to the ring, are oxidized to respective acids. Only electrolytic oxidation, ozonolysis, and a strong base cause ring opening.Reference of 45887-08-9

Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics