pyrazoles-derivatives

Identification of Novel d-Amino Acid Oxidase Inhibitors by in Silico Screening and Their Functional Characterization in Vitro was written by Katane, Masumi;Osaka, Naoko;Matsuda, Satsuki;Maeda, Kazuhiro;Kawata, Tomonori;Saitoh, Yasuaki;Sekine, Masae;Furuchi, Takemitsu;Doi, Issei;Hirono, Shuichi;Homma, Hiroshi. And the article was included in Journal of Medicinal Chemistry in 2013.Computed Properties of C9H7BrN2 This article mentions the following:

D-Amino acid oxidase (DAO) is a degradative enzyme that is stereospecific for d-amino acids, including d-serine and d-alanine, which are potential coagonists of the N-methyl-d-aspartate (NMDA) receptor. Dysfunction of NMDA receptor-mediated neurotransmission has been implicated in the onset of various mental disorders such as schizophrenia. Hence, a DAO inhibitor that augments the brain levels of d-serine and/or d-alanine and thereby activates NMDA receptor function is expected to be an antipsychotic drug, for instance, in the treatment of schizophrenia. In the search for potent DAO inhibitor(s), a large number of compounds were screened in silico, and several compounds were estimated as candidates. These compounds were then characterized and evaluated as novel DAO inhibitors in vitro. The results reported in this study indicate that some of these compounds are possible lead compounds for the development of a clin. useful DAO inhibitor and have the potential to serve as active site probes to elucidate the structure-function relationships of DAO. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Computed Properties of C9H7BrN2).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) 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.Computed Properties of C9H7BrN2

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

Design of Potent, Selective, and Orally Bioavailable Inhibitors of Cysteine Protease Cathepsin K was written by Tavares, Francis X.;Boncek, Virginia;Deaton, David N.;Hassell, Anne M.;Long, Stacey T.;Miller, Aaron B.;Payne, Alan A.;Miller, Larry R.;Shewchuk, Lisa M.;Wells-Knecht, Kevin;Willard, Derril H. Jr.;Wright, Lois L.;Zhou, Hui-Qiang. And the article was included in Journal of Medicinal Chemistry in 2004.Reference of 3528-58-3 This article mentions the following:

Osteoclast-mediated bone matrix resorption has been attributed to cathepsin K, a cysteine protease of the papain family that is abundantly and selectively expressed in osteoclast. Inhibition of cathepsin K could potentially be an effective method to prevent osteoporosis. Structure-activity studies on a series of reversible ketoamides based inhibitors of cathepsin K have led to identification of potent and selective compounds Crystallog. studies have given insights into the mode of binding of these inhibitors. A series of ketoamides with varying P1 moieties were first synthesized to find an optimum group that would fit into the S1 subsite of the cysteine protease, cathepsin K. With a desired P1 group in place a variety of heterocyclic analogs in the P’ region were synthesized to study their steric and electronic effects. In the process of exploring these P’ heterocyclic variations, excellent selectivity was gained over other highly homologous cysteine proteases, including cathepsins L, S, and V. The favorable pharmacokinetic properties of some of these cathepsin K inhibitors in rats make them suitable for evaluation in rodent osteoporosis models. A representative cathepsin K inhibitor was shown to attenuate PTH-stimulated hypercalcemia in the TPTX rat model. These inhibitors provide a viable lead series in the discovery of new therapies for the prevention and treatment of osteoporosis. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Reference of 3528-58-3).

1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3) 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.Reference of 3528-58-3

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

Solvent-Induced Structural Changes in Complexes of 1,2-Bis(3-(3-pyridyl)pyrazolyl)ethane was written by Prananto, Yuniar P.;Turner, David R.;Lu, Jinzhen;Batten, Stuart R.. And the article was included in Australian Journal of Chemistry in 2009.Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine This article mentions the following:

A series of complexes were obtained using the flexible ditopic ligand 1,2-bis(3-(3-pyridyl)pyrazolyl)ethane (L^Et) with M(SCN)₂ (M = Co, Fe) and ZnCl₂. The ligand exists in a variety of conformations with rotations around the ethane spacer and around the pyridyl/pyrazole bond. The bridging length of the ligand (i.e., distance between pyridyl nitrogen atoms) varies by 3.5 Å depending on its geometry. Three different cobalt(II) complexes of the general form [Co(L^Et)₂(SCN)₂]·Solv (Solv is a variable number/type of non-coordinated solvent) were structurally characterized and form a series of solvent dependant supramol. isomers. When Solv = 2MeCN a (4,4)-sheet is formed (1), however, when Solv = H₂O an alternate collapsed (4,4)-sheet is observed (2). Changing the solvent to two mols. of N,N-dimethylformamide (DMF) leads to a radical change in structure with a one-dimensional (1D) polymer formed (3) that contains two bridging ligands between adjacent metal atoms (i.e., maintaining the same metal/ligand ratio as in the (4,4)-sheet structures). A monomeric thiocyanate complex [Fe(L^Et)₂(SCN)₂(H₂O)₂] (4) is reported in which the bispyridyl ligands are terminal and partake in an extended hydrogen-bonded network. A 1D polymer [Zn(L^Et)Cl₂] (5) is also presented. The structures of the metal complexes are contrasted with that of the free ligand. In the experiment, the researchers used many compounds, for example, 3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine).

3-(1H-Pyrazol-3-yl)pyridine (cas: 45887-08-9) belongs to pyrazole derivatives. An alternative way to synthesize multisubstituted pyrazoles is the Csingle bondH arylation of simple pyrazoles. 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.Recommanded Product: 3-(1H-Pyrazol-3-yl)pyridine

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

Synthesis, cytotoxicity, and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinones was written by Raffa, Demetrio;Edler, Michael C.;Daidone, Giuseppe;Maggio, Benedetta;Merickech, Mourad;Plescia, Salvatore;Schillaci, Domenico;Bai, Ruoli;Hamel, Ernest. And the article was included in European Journal of Medicinal Chemistry in 2004.Synthetic Route of C5H9N3 This article mentions the following:

In order to study the influence of 3-substituents on the cytotoxic activity of 2-styrylquinazolinones, a series of 6-chloro-2-styryl-3-(heteroaryl)-4(3H)-quinazolinones, e.g. I, were synthesized by refluxing equimolar amounts of the corresponding 2-methyl-quinazolinones and benzaldehyde in glacial acetic acid. At 1 μg ml^-1 concentration, almost all the synthesized compounds showed some cytotoxic activity against the L1210 and K562 leukemia cell lines. However, only compound I inhibited the growth of these cells by over 50%. It was also found to be the only member of the series that inhibited tubulin polymerization, with an IC₅₀ value of 5.8 vs. 3.2 μM for control drug colchicine. I was further examined for effects on the growth of human MCF7 breast carcinoma cells and Burkitt lymphoma CA46 cells, which had IC₅₀ values of 0.34 and 1.0 μM, resp. At 10 μM, I induced G2/M arrest (66%) in Burkitt cells, with a mitotic index of 20%. At 3.4 μM, it caused disruption of the cellular microtubule system of the MCF7 cells. Both these cellular effects are consistent with its mechanism of action resulting from its inhibitory effect on tubulin assembly. In the experiment, the researchers used many compounds, for example, 1-Ethyl-1H-pyrazol-5-amine (cas: 3528-58-3Synthetic Route of C5H9N3).

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 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.Synthetic Route of C5H9N3

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

Direct nitration of five membered heterocycles was written by Katritzky, Alan R.;Scriven, Eric F. V.;Majumder, Suman;Akhmedova, Rena G.;Akhmedov, Novruz G.;Vakulenko, Anatoliy V.. And the article was included in ARKIVOC (Gainesville, FL, United States) in 2005.Synthetic Route of C4H5N3O2 This article mentions the following:

Direct nitration of a variety of furans, pyrroles, thiophenes, pyrazoles, imidazoles, isoxazoles and thiazoles (17 compounds) with nitric acid/trifluoroacetic anhydride affords mononitro derivatives in average yield of 60%. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1Synthetic Route of C4H5N3O2).

1-Methyl-3-nitro-1H-pyrazole (cas: 54210-32-1) 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. 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.Synthetic Route of C4H5N3O2

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

Michael addition of α-nitroacetate to α, β-unsaturated pyrazolamide catalyzed by triethylamine was written by Liu, Yingying;He, Qian;Chen, Feng;Li, Xuefeng. And the article was included in Shandong Huagong in 2018.Recommanded Product: 15953-73-8 This article mentions the following:

An efficient Michael addition of α-nitroacetate to α, β-unsaturated pyrazolamide was developed in the presence of triethylamine. Synthetically useful yields (50% ∼ 88%) have been achieved with various α, β-unsaturated pyrazolamides. The structures of adducts have been clearly confirmed by ¹H-NMR, ¹³C-NMR and HRMS anal. Adducts resulting from this protocol are useful synthetic intermediates for further synthetic modification. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Recommanded Product: 15953-73-8).

4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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: 15953-73-8

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

A simple and catalyst free one pot access to the pyrazolone fused 2,8-dioxabicyclo[3.3.1]nonanes was written by Bingi, Chiranjeevi;Emmadi, Narender Reddy;Chennapuram, Madhu;Nanubolu, Jagadeesh Babu;Atmakur, Krishnaiah. And the article was included in RSC Advances in 2014.Reference of 401-73-0 This article mentions the following:

A series of novel aryl and heteroaryl fused 2,8-dioxabicyclo[3.3.1]nonanes I (R = 4-Cl, 4-MeO, 4-Br, etc.; R¹ = C₆H₅, 2-BrC₆H₄, 4-CNC₆H₄, etc.; R² = H, Ph) was accomplished by one pot, catalyst free reaction of 2-hydroxy chalcones with 3-trifluoromethyl substituted pyrazolones in xylene at reflux temperature The role of the trifluoromethyl functional group in formation of I was confirmed by comparative studies with 3-Me substituted pyrazolones and the outcome is presented. In the experiment, the researchers used many compounds, for example, 3-(Trifluoromethyl)-1H-pyrazol-5(4H)-one (cas: 401-73-0Reference of 401-73-0).

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 can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Reference of 401-73-0

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

Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation was written by Cheng, Xiang;Wang, Wei;Wang, Yunxiao;Xia, Dongguo;Yin, Fang;Liu, Qiaoyun;Luo, Huisheng;Li, Meng;Zhang, Chengqi;Cao, Haiqun;Lv, Xianhai. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid This article mentions the following:

Plant pathogenic fungi seriously threaten agricultural production There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound (I) exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC₅₀ value of 1.25 mg/L, close to that of com. fungicide boscalid (EC₅₀ = 0.96 mg/L) and fluopyram (EC₅₀ = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to pos. control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound I may impede the growth and reproduction of S. sclerotiorum by affecting the morphol. of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound I did not injure the growth or reproduction of Italian bees. This study revealed that compound I is expected to be developed for efficient and safe agricultural fungicides. In the experiment, the researchers used many compounds, for example, 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid).

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. 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.Name: 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid

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

Chemiluminescence vs. Kjeldahl determination of nitrogen in oil shale retort waters and organonitrogen compounds was written by Jones, Bonnie M.;Daughton, Christian G.. And the article was included in Analytical Chemistry in 1985.Reference of 934-48-5 This article mentions the following:

The applicability of combustion/chemiluminescent N determination to determining N in oil shale wastewaters and various representative chem. classes was demonstrated. Only azoxy compounds and those containing the pyrazole nucleus were not amenable to anal. The majority of 56 compounds tested yielded 90-110% of their theor. N content; enhanced recovery was found for N oxide salts. For 12 oil shale wastewaters, combustion/chemiluminescence gave total N values (1100-28,800 mg/L) that did not differ statistically (P > 0.10) from those obtained by the time-consuming wet-chem. Kjeldahl method. The relative standard deviations for 10 replicates of each wastewater were less than 3.5%. No matrix or solvent effects were found. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Reference of 934-48-5).

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. 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.Reference of 934-48-5

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

The Reactivity Trends in Electrochemical Chlorination and Bromination of N-Substituted and N-Unsubstituted Pyrazoles* was written by Lyalin, B. V.;Petrosyan, V. A.. And the article was included in Chemistry of Heterocyclic Compounds (New York, NY, United States) in 2014.Application of 15953-73-8 This article mentions the following:

The authors’ study of electrochem. chlorination and bromination of pyrazoles decorated with electron-withdrawing and electron-donating groups showed that the product yield and composition depended on the substitution at the N-1 atom. The authors showed for the 1st time the significant differences in halogenation reactivity patterns of N-unsubstituted and N-alkylpyrazoles. In the experiment, the researchers used many compounds, for example, 4-Chloro-3,5-dimethyl-1H-pyrazole (cas: 15953-73-8Application of 15953-73-8).

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. 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.Application of 15953-73-8

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