Category: pyrazoles-derivatives

Pyrazoles. XXXVI. Chromatography of pyrazoles in unfixed thin layer of aluminum oxide was written by Kost, A. N.;Faizova, G. K.;Grandberg, I. I.. And the article was included in Zhurnal Obshchei Khimii in 1963.COA of Formula: C5H7ClN2 This article mentions the following:

The R_f values are tabulated for 48 substituted pyrazoles in thin layer Al₂O₃ chromatography. Solvent system of petr. ether-CHCl₃ was satisfactory for separation of 1-alkylpyrazoles; pyrazoles without 1-substituent moved but little in this system, but gave good movement in systems such as C₆H₆-MeOH or C₆H₆-Me₂CO. Mixtures of isomeric substituted pyrazoles were effectively separated by this procedure. Some difficulty was encountered in separation of 1-phenyl-3- and -4-halopyrazoles only. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8COA of Formula: C5H7ClN2).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.COA of Formula: C5H7ClN2

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

Optimization of Novel 1-Methyl-1H-Pyrazole-5-carboxamides Leads to High Potency Larval Development Inhibitors of the Barber’s Pole Worm was written by Le, Thuy G.;Kundu, Abhijit;Ghoshal, Atanu;Nguyen, Nghi H.;Preston, Sarah;Jiao, Yaqing;Ruan, Banfeng;Xue, Lian;Huang, Fei;Keiser, Jennifer;Hofmann, Andreas;Chang, Bill C. H.;Garcia-Bustos, Jose;Jabbar, Abdul;Wells, Timothy N. C.;Palmer, Michael J.;Gasser, Robin B.;Baell, Jonathan B.. And the article was included in Journal of Medicinal Chemistry in 2018.Synthetic Route of C5H9N3 This article mentions the following:

A phenotypic screen of a diverse library of small mols. for inhibition of the development of larvae of the parasitic nematode Haemonchus contortus led to the identification of a 1-methyl-1H-pyrazole-5-carboxamide derivative with an IC₅₀ of 0.29 μM. Medicinal chem. optimization targeted modifications on the left-hand side (LHS), middle section, and right-hand side (RHS) of the scaffold to elucidate the structure-activity relation (SAR). Strong SAR allowed for the iterative and directed assembly of a focus set of 64 analogs, from which compound 60 was identified as the most potent compound, inhibiting the development of the fourth larval (L4) stage with an IC₅₀ of 0.01 μM. In contrast, only 18% inhibition of the mammary epithelial cell line MCF10A viability was observed, even at concentrations as high as 50 μM. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4Synthetic Route of C5H9N3).

1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4) 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. 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. Synthetic Route of C5H9N3

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

Thermal rearrangement of v-triazolo[1,5-a]pyridine-3-acraldehydes into 3-methyl-5-(2-pyridyl) pyrazoles was written by Jones, Gurnos;Davies, Leslie Stuart. And the article was included in Journal of the Chemical Society [Section] C: Organic in 1971.Synthetic Route of C9H9N3 This article mentions the following:

The cis-v-triazolo[1,5-a]pyridine-3-acraldehyde (I) was thermally rearranged to 3-methyl-5-(2-pyridyl)pyrazole-4-carboxaldehyde (II) and 3-methyl-5-(2-pyridyl)pyrazole (III). The trans isomer of I gave only III. KMnO4 oxidation of II gave the corresponding acid, which was decarboxylated to III. III was prepared by the reaction of 1-(2-pyridyl)-1,3-butanedione with N2H4. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4Synthetic Route of C9H9N3).

2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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.Synthetic Route of C9H9N3

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

Proton magnetic resonance studies of pyrazoles was written by Tensmeyer, L. G.;Ainsworth, C.. And the article was included in Journal of Organic Chemistry in 1966.Application of 10199-53-8 This article mentions the following:

4-Proton chem. shift data for 54 pyrazoles are correlated in the empirical equation δ4 = δ4(s) + α₁ + α₃ + α₅, where δ4(s) is a constant for each solvent, and α₁, α₃, and α₅ are empirical constants that represent the effect of replacing a methyl substituent by another group at positions 1, 3, and 5 of the pyrazole nucleus. The equation can be used for isomer identification and for the study of tautomers. The α constants of the equation are correlated with Hammett σ constants In the N.M.R. spectra, a phenyl group attached to a pyrazole ring appears as a multiplet resonance unless a substituent is α to it. Under the latter condition the phenyl resonance is a singlet. Chem. shift data are used to distinguish relative coplanarity of the phenyl and pyrazole rings. Ring proton coupling constants of pyrazoles are discussed. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Application of 10199-53-8).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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.Application of 10199-53-8

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

Design, synthesis, characterization and pharmacological evaluation of antimycobacterial agents targeting dapb (dihydrodipicolinate reductase) was written by Hemalatha, B.;Shanthakumar, B.;Sekar, A. M.. And the article was included in International Journal of Pharmaceutical Sciences Review and Research in 2013.Product Details of 5334-39-4 This article mentions the following:

Pyrazole, a heterocyclic nucleus were found to exhibit a wide range of biol. activities were selected to prepare a database which was then docked against dihydrodipicolinate reductase (dapB) using Glide software (Maestro version -9.1) for antitubercular activity. The compounds with top scores were selected, synthesized, characterized by IR, NMR and mass spectroscopy and screened for in-vitro antitubercular activity by microplate alamar blue assay. All compounds shows a significant antitubercular activity at the min. inhibitory concentration varied between 25μg/mL and 100μg/mL. Inhibition was compared using pyrazinamide 3.125μg/mL and streptomycin 6.25μg/mL as standard In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Product Details of 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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. Product Details of 5334-39-4

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

Reactions with 5-trifluoromethyl-2,4-dihydropyrazol-3-one derivatives: a new route for the synthesis of fluorinated polyfunctionally substituted pyrazole and pyrano[2,3-c]pyrazole derivatives was written by Zohdi, Hussein F.;Elghandour, Ahmed H. H.;Rateb, Nora M.;Sallam, Mohamed M. M.. And the article was included in Journal of Chemical Research, Synopses in 1992.Safety of 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one This article mentions the following:

Reaction of trifluoromethylpyrazolones I (R = H, Ph) with R¹CH:C(CN)₂ (R¹ = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-ClC₆H₄, 2-furyl) in the presence of piperidine gave pyranopyrazoles II. Cyclocondensation of I (R = Ph) with R¹COCH₂COR² (R¹ = Me, CF₃; R² = OEt, NHPh) gave pyranopyrazoles III (R¹ = Me, CF₃). I (R = Ph) reacted with dibenzoylmethane and acetylacetone to give derivatives IV and V resp. The reactions of I (R = Ph) with aromatic aldehydes are also reported. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Safety of 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one).

3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Safety of 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one

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

Cytotoxic activity of some novel sulfonamide derivatives was written by Ghorab, Mostafa M.;Alsaid, Mansour S.;Abdullah-Al-Dhfyan;Arafa, Reem K.. And the article was included in Acta Poloniae Pharmaceutica in 2015.COA of Formula: C5H9N3 This article mentions the following:

The versatile synthons 2-chloro-N-(4-sulfamoylphenyl)acetamides 1a,b were used as a key intermediates for the synthesis of sulfonamide derivatives with adamantyl 2, indene 3, morpholinophenyl 4, pipronyl 5, benzothiazole 6-8, pyrazole 9, thiadiazole 10, 11, quinoline 12, isoquinoline 13, thiazoles 14-19, acrylamides 20-24 and benzochromene 25 moieties via reaction with several nitrogen nucleophiles. The newly synthesized compounds were screened in vitro for their anticancer activity against breast cancer (MDA-MB-231) and colon cancer (HT-29) cell lines. Compound 17 was found to be the most potent against breast cancer cell lines with IC50 value 66.6 μM compared with the reference drug 5-fluorouracil with IC50 value 77.28 μM. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3COA of Formula: C5H9N3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.COA of Formula: C5H9N3

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

Depsipeptides featuring a neutral P1 are potent inhibitors of kallikrein-related peptidase 6 with on-target cellular activity was written by De Vita, Elena;Schueler, Peter;Lovell, Scott;Lohbeck, Jasmin;Kullmann, Sven;Rabinovich, Eitan;Sananes, Amiram;Hessling, Bernd;Hamon, Veronique;Papo, Niv;Hess, Jochen;Tate, Edward W.;Gunkel, Nikolas;Miller, Aubry K.. And the article was included in Journal of Medicinal Chemistry in 2018.Computed Properties of C4H5N3O2 This article mentions the following:

Kallikrein-related peptidase 6 (KLK6) is a secreted serine protease that belongs to the family of tissue kallikreins (KLKs). Many KLKs are investigated as potential biomarkers for cancer as well as therapeutic drug targets for a number of pathologies. KLK6, in particular, has been implicated in neurodegenerative diseases and cancer, but target validation has been hampered by a lack of selective inhibitors. This work introduces a class of depsipeptidic KLK6 inhibitors, discovered via high-throughput screening, which were found to function as substrate mimics that transiently acylate the catalytic serine of KLK6. Detailed structure-activity relationship studies, aided by in silico modeling, uncovered strict structural requirements for potency, stability, and acyl-enzyme complex half-life. An optimized scaffold, DKFZ-251, demonstrated good selectivity for KLK6 compared to other KLKs, and on-target activity in a cellular assay. Moreover, DKFZ-633, an inhibitor-derived activity-based probe, could be used to pull down active endogenous KLK6. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Computed Properties of C4H5N3O2).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) 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. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Computed Properties of C4H5N3O2

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

Investigation of ESIPT in a panel of chromophores presenting N-H···N intramolecular hydrogen bonds was written by Hubin, Pierre O.;Laurent, Adele D.;Vercauteren, Daniel P.;Jacquemin, Denis. And the article was included in Physical Chemistry Chemical Physics in 2014.Product Details of 19959-77-4 This article mentions the following:

Thermodn. and kinetic aspects of excited state intramol. proton transfer (ESIPT) are investigated in 11 chromophores harboring an intramol. N-H···N hydrogen bond [pyridyl pyrazole, pyridyl pyrrole, azaindole, pyridyl indole, pyrroloquinoline, and an analog of the Blue Fluorescent Protein (BFP) chromophore] with the help of quantum mech. calculations For pyridyl pyrazoles, simulated spectra are used to help the interpretation of exptl. ones and the effects of several substituents are investigated. Then it is shown that Time-Dependent D. Functional Theory fails to satisfactorily describe the energetic aspects of ESIPT for the BFP chromophore analog. Equation-of-Motion Coupled Cluster theory is thus used to reach accurate insights for this challenging case. In the experiment, the researchers used many compounds, for example, 2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4Product Details of 19959-77-4).

2-(5-Methyl-1H-pyrazol-3-yl)pyridine (cas: 19959-77-4) 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.Product Details of 19959-77-4

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

K₂CO₃-Promoted Pyrazoles Synthesis from 1,3-Dipolar Cycloaddition of N-Tosylhydrazones with Acetylene Gas was written by Li, Dongying;Qiu, Shanguang;Chen, Yuxue;Wu, Luyong. And the article was included in ChemistrySelect in 2020.Formula: C9H7BrN2 This article mentions the following:

A series of pyrazoles I (R¹ = Me, Ph, 4-(trifluoromethyl)phenyl, etc.; R² = H, Me, Ph, 4-chlorophenyl, etc.) was provided in mediate to good yields. The 1,3-dipolar cycloaddition of N-tosylhydrazones 2-R³-3-R⁴-4-R⁵-C₆H₂C(R⁶)=NNHS(O)₂(4-CH₃C₆H₄) [R³ = H, Me, OMe; R⁴ = H, Me, Br, Cl; R⁵ = H, Me, N(CH₃)₂, OMe, Br, CF₃, Cl; R⁶ = H, Me] (II) with acetylene gas on balloon was investigated. Bases and solvents were screened and K₂CO₃ was verified to be an efficient base to promote this process. DMSO gave the better result in the reaction of N-tosylhydrazones derived from aldehyde II (R⁶ = H), and NMP was a better suitable solvent in the reaction of ketone N-tosylhydrazones II (R⁶ = Me). This process was easy to handle and suitable to the industrial application. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Formula: C9H7BrN2).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) 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. Protonation of pyrazole in strong acid leads to pyrazolium cations, which undergo electrophilic substitution preferentially at C3 rather than C4. The pyrazole anion is not reactive toward nucleophiles but is mostly reactive to electrophiles.Formula: C9H7BrN2

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