Month: December 2022

Studies on pyrazolo[3,4-d]pyrimidine derivatives. XVIII. Facile preparation of 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-ones was written by Miyashita, Akira;Iijima, Chihoko;Higashino, Takeo;Matsuda, Hideaki. And the article was included in Heterocycles in 1990.Related Products of 18213-75-7 This article mentions the following:

Reaction of 5-amino-1-phenyl-1H-pyrazole-4-carboxamide (I, R = Ph) with R¹CO₂R² (II, R¹ = H, Me, Et, Pr, Me₂CH, PHCH₂, CO₂Et, Ph; R² = Me, Et) in the presence of EtONa-EtOH gave 1-phenylpyrazolopyrimidinones III (R = Ph). Similar treatment of I (R = Me) with II gave III (R = Me). In the experiment, the researchers used many compounds, for example, 5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7Related Products of 18213-75-7).

5-Amino-1-methyl-1H-pyrazole-4-carboxamide (cas: 18213-75-7) 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. Related Products of 18213-75-7

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

Transition metal organometallic complexes containing 3-substituted poly(pyrazolyl)borate ligands. Part 1. Formation of η²-aroyl, η¹-halocarbyne or sterically crowded aryldiazenide ligands in the reactions of ring-substituted tricarbonyl[hydrotris(pyrazolyl)borato]molybdate and -tungstate anions with arenediazonium cations and related oxidants was written by Lalor, Fergus J.;Desmond, Timothy J.;Cotter, Gerard M.;Shanahan, Claire A.;Ferguson, George;Parvez, Masood;Ruhl, Barbara. And the article was included in Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry in 1995.Computed Properties of C5H7ClN2 This article mentions the following:

Although the hydrotris(pyrazolyl)borato complex [Mo{HB(pz)₃}(CO)₃]^– reacted with 3- or 4-substituted arenediazonium cations [R’N₂]⁺ yielding carbonyl-substitution (i.e. aryldiazenido) products [Mo{HB(pz)₃}(CO)₂(N₂R’)], reaction of the Me-substituted analog [ML^*(CO)₃]^– [L^* = tris(3,5-dimethylpyrazolyl)hydroborate; M = Mo or W] led, via oxidative formation of aryl radicals and [ML^*(CO)₃]^•, to η²-aroyl complexes [ML^*(CO)₂(η²-COR’)] [R’ = C₆H₄X-4 (X = NO₂, CN, COMe, CF₃, H, Me, OMe or NMe₂) or C₆H₄X-3 (X = NO₂ or OMe)] in MeCN or to the halocarbyne complexes [ML^*(CO)₂(CX)] (X = Cl, Br or I) in the presence of the haloalkanes CH₂Cl₂ or CHX₃ (X = Br or I). [MoL^*(CO)₃]^– reacted similarly with diphenyliodonium or triphenylsulfonium cations, but in the latter case anion-cation redox is very slow in the dark but rapid upon irradiation with sunlight. Comparison of these results with those obtained for [ML^*(CO)₃]^– analogs with different substituents in the pyrazolyl rings demonstrates that oxidation of the former by arenediazonium cations occurs in response to the steric rather than the electronic effect of the 3-Me substituents. However, further steric crowding in either the hydrotris(pyrazolyl)borate ligand or the diazonium cation promotes a reversion to the carbonyl-substitution pathway. A mechanism to account for these observations is proposed. Attempts to extend the chlorocarbyne synthesis to systems other than [ML^*(CO)₃]^– met with only limited success. Spectroscopic data for the new complexes are reported and discussed. Two aryldiazenido complexes, [MoL^*(CO)₂(N₂R’)] (R’ = 2,6-Me₂C₆H₃ or 2,3-dimethyl-5-oxo-1-phenyl-3-pyrazolin-4-yl) were characterized by single-crystal x-ray diffraction studies and were found to differ in the manner in which the aryldiazenide ligand accommodates to steric crowding in the Mo coordination sphere. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Computed Properties of C5H7ClN2).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) 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. 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 C5H7ClN2

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

An efficient solvent-free synthesis of NH-pyrazoles from β-dimethylaminovinylketones and hydrazine on grinding was written by Longhi, Kelvis;Moreira, Dayse N.;Marzari, Mara R. B.;Floss, Vagner M.;Bonacorso, Helio G.;Zanatta, Nilo;Martins, Marcos A. P.. And the article was included in Tetrahedron Letters in 2010.Formula: C9H7BrN2 This article mentions the following:

A series of NH-pyrazoles was efficiently synthesized from the reaction of β-dimethylaminovinylketones ([R¹C(O)C(R²)=CHN(Me₂)], where R¹ = Me, Ph, 3-MeO-Ph, 4-Me-Ph, 4-MeO-Ph, 4-F-Ph, 4-Cl-Ph, 4-Br-Ph, 4-O₂N-Ph, fur-2-yl, thien-2-yl; R² = H, 2-MeO-Ph; R¹, R² = -(CH₂)₃C(O)-) and hydrazine sulfate in solid state on grinding in the presence of p-toluenesulfonic acid (PTSA). Most of the reactions proceeded smoothly at room temperature under solvent-free conditions. In comparison with the classical reaction conditions, which employ mol. solvent (ethanol), this new synthetic method has the advantages of shorter times, higher yields, mild reaction conditions as well as being environmentally friendly. 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 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: C9H7BrN2

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

Spectral and thermal studies on ruthenium carbonyl complexes with 5-trifluoromethyl-2,4-dihydropyrazol-3-one ligands was written by Soliman, Ahmed A.. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2007.Computed Properties of C4H3F3N2O This article mentions the following:

Reactions of the cluster compound [Ru₃(CO)₁₂] with 5-trifluoromethyl-2,4-dihydropyrazol-3-one (HL¹), 4-(2,4-dichlorophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H₂L²), 4-(3-fluorophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H₂L³), 4-(3-(trifluoromethyl)phenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H₂L⁴) and 4-(3-nitrophenylhydrazono)-5-trifluoromethyl-2,4-dihydropyrazol-3-one (H₂L⁵) were carried out in benzene and under reduced pressure. The structures of the isolated complexes were elucidated using elemental analyses, IR, UV-visible, mass and NMR spectroscopy. All the complexes are diamagnetic and have trigonal bipyramidal structures [Ru(CO)₄(HL¹)] and [Ru(CO)₃(H₂L^2-5)]. The thermal decompositions of the complexes were studied in correlation with the mass spectral fragmentation patterns. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Computed Properties of 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. 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.Computed Properties of C4H3F3N2O

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

Rescoring Docking Hit Lists for Model Cavity Sites: Predictions and Experimental Testing was written by Graves, Alan P.;Shivakumar, Devleena M.;Boyce, Sarah E.;Jacobson, Matthew P.;Case, David A.;Shoichet, Brian K.. And the article was included in Journal of Molecular Biology in 2008.Reference of 5334-39-4 This article mentions the following:

Mol. docking computationally screens thousands to millions of organic mols. against protein structures, looking for those with complementary fits. Many approximations are made, often resulting in low “hit rates.”. A strategy to overcome these approximations is to rescore top-ranked docked mols. using a better but slower method. One such is afforded by mol. mechanics-generalized Born surface area (MM-GBSA) techniques. These more phys. realistic methods have improved models for solvation and electrostatic interactions and conformational change compared to most docking programs. To investigate MM-GBSA rescoring, the authors reranked docking hit lists in three small buried sites: a hydrophobic cavity that binds apolar ligands, a slightly polar cavity that binds aryl and hydrogen-bonding ligands, and an anionic cavity that binds cationic ligands. These sites are simple; consequently, incorrect predictions can be attributed to particular errors in the method, and many likely ligands may actually be tested. In retrospective calculations, MM-GBSA techniques with binding-site minimization better distinguished the known ligands for each cavity from the known decoys compared to the docking calculation alone. This encouraged us to test rescoring prospectively on mols. that ranked poorly by docking but that ranked well when rescored by MM-GBSA. A total of 33 mols. highly ranked by MM-GBSA for the three cavities were tested exptl. Of these, 23 were observed to bind-these are docking false negatives rescued by rescoring. The 10 remaining mols. are true negatives by docking and false positives by MM-GBSA. X-ray crystal structures were determined for 21 of these 23 mols. In many cases, the geometry prediction by MM-GBSA improved the initial docking pose and more closely resembled the crystallog. result; yet in several cases, the rescored geometry failed to capture large conformational changes in the protein. Intriguingly, rescoring not only rescued docking false positives, but also introduced several new false positives into the top-ranking mols. The authors consider the origins of the successes and failures in MM-GBSA rescoring in these model cavity sites and the prospects for rescoring in biol. relevant targets. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Reference of 5334-39-4).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) 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. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Reference of 5334-39-4

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

A structural study of pyrazole-1-carboxamides by X-ray crystallography and ¹³C CPMAS NMR spectroscopy was written by Llamas-Saiz, Antonio L.;Foces-Foces, Concepcion;Sobrados, Isabel;Jagerovic, Nadine;Elguero, Jose. And the article was included in Journal of Molecular Structure in 1999.Product Details of 934-48-5 This article mentions the following:

The crystal structures of the 1st two pyrazole N-substituted primary amides (3-Me and 4-bromo) were determined Crystallog. data and at. coordinates are given. The amide groups from the R₂²(8) H-bond dimeric pattern in all cases, in accordance with the higher rate found for the formation of this pattern in monosubstituted benzamides (81%) compared with the whole group of primary amide structures (34%). These two compounds and four other N-CONH₂ pyrazoles were studied by solid state NMR (CPMAS technique). In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Product Details of 934-48-5).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) 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.Product Details of 934-48-5

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

Studies on 3′-quaternary ammonium cephalosporins. IV. Synthesis and antibacterial activity of 3′-(2-alkyl-3-aminopyrazolium)cephalosporins related to FK037 was written by Ohki, Hidenori;Kawabata, Kohji;Inamoto, Yoshiko;Okuda, Shinya;Kamimura, Toshiaki;Sakane, Kazuo. And the article was included in Bioorganic & Medicinal Chemistry in 1997.Recommanded Product: 3528-58-3 This article mentions the following:

The synthesis and in vitro antibacterial activity of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]cephalosporins bearing various 2-alkyl-3-aminopyrazolium groups at the 3-position are described. Antibacterial activity against MRSA was affected by the nature of the substituent at the 2-position on the 3′-aminopyrazolium groups. Among the cephalosporins prepared in this study, 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)pyrazolio]methyl-3-cephem-4-carboxylate sulfate (FK037) (I) showed extremely potent broad-spectrum activity against both Gram-pos. bacteria including MRSA, and Gram-neg. bacteria including Pseudomonas aeruginosa. The in vivo activity against MRSA of FK037 was the highest of all the β-lactam antibiotics tested. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Recommanded Product: 3528-58-3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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.Recommanded Product: 3528-58-3

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

Inhibitory effects of pyrazoles on soil nitrification: effects of chemical structure was written by Shi, Yunfeng;Zhang, Lili;Wu, Zhijie. And the article was included in Fresenius Environmental Bulletin in 2012.Computed Properties of C6H9N3O This article mentions the following:

Pyrazoles are nitrification inhibitors with good inhibitory effects. In this study, chem. structure of pyrazoles and its relationship with nitrification inhibitory effects were studied through aerobic incubation, and the optimal concentrations of three nitrification inhibitors with better nitrification inhibitory effects were explored, including 3,4-dimethylpyrazole phosphate (DMPP), 1-carboxamide-3-methylpyrazole (CMP), and 4-chloro-3-methylpyrazole (ClMP). The results showed that all the pyrazoles could effectively inhibit NH₄⁺ oxidation in soils. Specifically, inhibitory effects of 3-methylpyrazole, 3,4-dimethylpyrazole, 4-chloro-3-methylpyrazole and their derivatives were the best. When the 4-position was substituted by chlorine atoms, nitrification inhibitory effects of pyrazoles could be significantly improved, which were not affected by the substitution at 1-position (hydroxymethylation and amidation) and neutralization. Nitrification inhibitory rate and inhibitory duration were increased with increasing consumptions of nitrification inhibitor pyrazoles. The optimal concentrations of three nitrification inhibitors with better nitrification inhibitory effects, including DMPP, CMP and ClMP, should be controlled in the range of 0.25-1.0% of N application, and the nitrification duration was about 56 days. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Computed Properties of C6H9N3O).

3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) 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 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.Computed Properties of C6H9N3O

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

Discovery and structure-activity relationships of a novel class of quinazoline glucokinase activators was written by Iino, Tomoharu;Sasaki, Yasuhiro;Bamba, Makoto;Mitsuya, Morihiro;Ohno, Akio;Kamata, Kenji;Hosaka, Hideka;Maruki, Hiroko;Futamura, Mayumi;Yoshimoto, Riki;Ohyama, Sumika;Sasaki, Kaori;Chiba, Masato;Ohtake, Norikazu;Nagata, Yasufumi;Eiki, Jun-ichi;Nishimura, Teruyuki. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Category: pyrazoles-derivatives This article mentions the following:

We describe design, syntheses and structure-activity relationships of a novel class of 4,6-disubstituted quinazoline glucokinase activators. Prototype quinazoline leads were designed based on the X-ray analyses of the previous 2-aminobenzamide lead classes. Modifications of the quinazoline leads led to the identification of a potent GK activator I. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4Category: pyrazoles-derivatives).

1-Ethyl-1H-pyrazol-3-amine (cas: 55361-49-4) 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 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.Category: pyrazoles-derivatives

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

Synthesis, metabolism and structure-mutagenicity relationships of novel 4-nitro-(imidazoles and pyrazoles) in Salmonella typhimurium was written by Hrelia, Patrizia;Fimognari, Carmela;Maffei, Francesca;Brighenti, Benedetta;Garuti, Laura;Burnelli, Silvia;Cantelli-Forti, Giorgio. And the article was included in Mutation Research, Fundamental and Molecular Mechanisms of Mutagenesis in 1998.Electric Literature of C4H5N3O2 This article mentions the following:

A new series of 4-nitro-(imidazoles and pyrazoles) were synthesized as novel antimycotics and tested for their activation to mutagenic forms using Salmonella typhimurium TA98 and TA100, in the presence and in the absence of metabolic activation. TA100NR, TA100/1,8-DNP₆, YG1026 and YG1029 strains were employed to identify a specific metabolic reaction which governs the mutagenic potency. Derivatives in the pyrazole group were generally found to be non mutagenic and active imidazoles were weak-direct-acting mutagens. For most of the compounds the mutagenic responses in TA98 were absent or 12- to 22-fold lower compared to TA100. The presence of a Me or a benzylic group on the imidazole ring and substituents on the N₁ and N₃ positions were determinant for mutagenicity. Metabolism by bacterial enzyme systems was important to the expression of genotoxicity. Active compounds showed no mutagenicity toward the strain defective in classical nitroreductase and increased mutagenicity, from 2- to 7-fold depending on the test compound, toward the corresponding overproducing bacteria. On the other hand, compounds displayed reduced mutagenicity to the O-acetyltransferase strain without having increased activity in the corresponding overproducing bacteria, YG1029. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4Electric Literature of C4H5N3O2).

3-Methyl-4-nitro-1H-pyrazole (cas: 5334-39-4) 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.Electric Literature of C4H5N3O2

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