Tag: 200-300

Novel crown ether functionalized imidazolium-based acidic ionic liquid catalyzed synthesis of pyrazole derivatives under solvent-free conditions was written by Patil, Dayanand;Chandam, Dattatraya;Mulik, Abhijeet;Jagdale, Suryabala;Patil, Prasad;Deshmukh, Madhukar. And the article was included in Research on Chemical Intermediates in 2015.Product Details of 73387-46-9 This article mentions the following:

An innovative designed novel crown ether functionalized imidazolium-based reusable acidic ionic liquid [crown ether MIm] [HSO₄] has been efficiently implemented for the synthesis of pyrazole derivatives using various substituted enaminones, hydrazine hydrate and Ph hydrazine under solvent-free conditions. Structural novelty and task efficiency of the catalyst, high yields of desired products, greener approach attributing high atom economy (green chem. method) and solvent-free conditions render this protocol suitable to cope with the current demand in contemporary organic chem. The inventive idea of utilizing crown ether functionalized ionic liquid as a catalyst was for the first time demonstrated in this protocol. The synthesis of the target compounds was achieved using [6-[1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl]hexyl]imidazolium sulfate as a catalyst. Starting materials included hydrazine, phenylhydrazine and enaminone derivatives [(amino)alkenone derivatives] such as 3-(dimethylamino)-1-phenyl-2-propen-2-one, 3-(dimethylamino)-1-(2-furanyl)-2-propen -1-one, 2-[(dimethylamino)methylene]-1,3-cyclohexanedione. The title compounds thus formed included pyrazole derivatives and analogs, such as 3-phenyl-1H-pyrazole, 3-(2-furanyl)-1H-pyrazole, 1,5,6,7-tetrahydro-4H-indazol-4-one (indazole derivatives). In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Product Details of 73387-46-9).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) 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.Product Details of 73387-46-9

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

Synthesis and biological activities of 3-substituted-6- pyrazolyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles was written by An, Yue;Yao, Mingxing;Zhou, Xiaoxia;Liu, Mingyang. And the article was included in Yingyong Huaxue in 2014.Synthetic Route of C11H10N2O2 This article mentions the following:

The three kinds of 1-methyl-5-substituted-pyrazole-3-carboxylic acid were obtained by 5-substituted-1H-pyrazole-3-Et formate based on methylation and hydrolysis of the ester. Then the six kinds of 3-substituted-4-amino-5-mercapto-1,2,4-triazole were obtained using the substituted carboxylic acid by a series of reaction. Finally, eighteen novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles compounds were synthesized by phosphorus chloride treatment of the above two obtained intermediate. The structures of all new compounds were characterized by IR, ¹H NMR, ¹³C NMR and elemental analyses. The preliminary test shows that all the compounds display plant growth regulator activity and antibacterial activity. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Synthetic Route of C11H10N2O2).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) belongs to pyrazole derivatives. Pyrazole is a weak base, with pKb 11.5 (pKa of the conjugated acid 2.49 at 25 鎺矯).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. Synthetic Route of C11H10N2O2

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

Diphenylurea derivatives for combating methicillin- and vancomycin-resistant Staphylococcus aureus was written by Eissa, Ibrahim H.;Mohammad, Haroon;Qassem, Omar A.;Younis, Waleed;Abdelghany, Tamer M.;Elshafeey, Ahmed;Abd Rabo Moustafa, Mahmoud M.;Seleem, Mohamed N.;Mayhoub, Abdelrahman S.. And the article was included in European Journal of Medicinal Chemistry in 2017.Synthetic Route of C11H10N2O2 This article mentions the following:

A new class of diphenylurea was identified as a novel antibacterial scaffold with an antibacterial spectrum that includes highly resistant staphylococcal isolates, namely methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA). Starting with a lead compound that carries an aminoguanidine functionality from one side and a Bu moiety on the other ring, several analogs were prepared Considering the pharmacokinetic parameters as a key factor in structural optimization, the structure-activity-relationships (SARs) at the lipophilic side chain were rigorously examined leading to the discovery of the cycloheptyloxyl analog I as a potential drug-candidate. This compound has several notable advantages over vancomycin and linezolid including rapid killing kinetics against MRSA and the ability to target and reduce the burden of MRSA harboring inside immune cells (macrophages). Furthermore, the potent anti-MRSA activity of I was confirmed in vivo using a Caenorhabditis elegans animal model. The present study provides a foundation for further development of diphenylurea compounds as potential therapeutic agents to address the burgeoning challenge of bacterial resistance to antibiotics. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Synthetic Route of C11H10N2O2).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) 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. 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 C11H10N2O2

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

Metal-free Cross-Dehydrogenative Coupling of HN-azoles with 浼?C(sp³)-H Amides via C-H Activation and Its Mechanistic and Application Studies was written by Aruri, Hariprasad;Singh, Umed;Kumar, Mukesh;Sharma, Sumit;Aithagani, Sravan Kumar;Gupta, Vivek K.;Mignani, Serge;Vishwakarma, Ram A.;Singh, Parvinder Pal. And the article was included in Journal of Organic Chemistry in 2017.Application of 73387-46-9 This article mentions the following:

A metal-free one step coupling reaction between various N-azole rings and diverse 浼?C(sp³)-H containing amides has been developed under oxidative reaction conditions. Com. available tetrabutylammonium iodide (TBAI) in the presence of tert-Bu hydroperoxide (TBHP), under neat reaction conditions, efficiently catalyzed the coupling. Various azole types, such as 1H-benzotriazoles, 1H-1,2,3-triazoles, 1H-1,2,4-triazoles, 1H-tetrazoles, 1H-pyrazoles, and 1H-benzimidazoles, and 浼?C(sp³)-H containing amides, such as N,N-dimethylacetamide, N,N-dimethylbenzamide, N-methylacetamide, N,N-diethylacetamide, N-methylpyrrolidine, and pyrrolidin-2-one, were successfully employed for the coupling. A series of designed and controlled experiments were also performed in order to study the involvement of the different intermediates. Based on the evidence, a plausible mechanism is also proposed. These novel, simple, rapid, attractive, and straightforward transformations open the way of the construction of novel highly functionalized N-azoles via direct covalent N-H bond transformations onto N-C bonds. This approach allows to the synthesis of complex mols. requiring number of steps using classical synthetic ways. In addition, the range of 浼?C(sp³)-H containing amide substrates is virtually unlimited highlighting the potential value of this simple system for the construction of complex heterocyclic mols., such as fused azole derivatives In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Application of 73387-46-9).

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閳ユ徆onor motifs, whether as a monocyclic ring or as a fused indazole ring. 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.Application of 73387-46-9

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

Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles was written by Khachikyan, R. Dzh.;Ovakimyan, Z. G.;Panosyan, G. A.;Tamazyan, R. A.;Ayvazyan, A. G.. And the article was included in Russian Journal of General Chemistry in 2016.Category: pyrazoles-derivatives This article mentions the following:

Reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives I•HCl (R = Me, Cl, Br) regardless of pH and a solvent nature. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to gave (Z)-2-[(β-aroylvinyl)sulfanyl]-4 arylpyrimidines II (R = Me, Cl, Br). In the case of N,N’-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides III•Br^– (R = Me, Cl, Br). Pyridine hydrobromide liberated in the reaction course had a major influence on the process chemoselectivity. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Category: pyrazoles-derivatives).

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.Category: pyrazoles-derivatives

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

Application of Free-Wilson models in spectroscopy. Reevaluation of the Tensmeyer additivity system in the proton NMR of pyrazoles was written by Cativiela, C.;Garcia, J. I.;Elguero, J.. And the article was included in Anales de Quimica, Serie C: Quimica Organica y Bioquimica in 1987.Electric Literature of C11H10N2O2 This article mentions the following:

Modified coefficients of the Tensmeyer additivity system are used to calculate ¹H NMR chem. shifts δ(4-H) of the proton at the 4-position of 1,3,5-substituted pyrazoles. The coefficients were reevaluated by using a more accurate math. procedure. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Electric Literature of C11H10N2O2).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) 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.Electric Literature of C11H10N2O2

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

Lanthanide pyrazolecarboxylates for OLEDs and bioimaging was written by Utochnikova, Valentina V.;Latipov, Egor V.;Dalinger, Alexander I.;Nelyubina, Yulia V.;Vashchenko, Andrey A.;Hoffmann, Michael;Kalyakina, Alena S.;Vatsadze, Sergey Z.;Schepers, Ute;Brase, Stefan;Kuzmina, Natalia P.. And the article was included in Journal of Luminescence in 2018.Reference of 10199-53-8 This article mentions the following:

Novel materials based on lanthanide complexes with six pyrazolecarboxylates were obtained. They possess high solubility due to the purposeful introduction of the nitrogen heteroatom in α-position to the carboxy-group, and their luminescence quantum yields reach 100%. High absorption and non-toxicity allowed their successful use for bioimaging in cellulo. While the special approach to electron transport enhancement allowed using them as OLED emission materials. In the experiment, the researchers used many compounds, for example, 1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8Reference of 10199-53-8).

1-Methyl-5-phenyl-1H-pyrazole-3-carboxylic acid (cas: 10199-53-8) 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. 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.Reference of 10199-53-8

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

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