Tag: 200-300

A simple and efficient synthesis of pyrazoles in water was written by Wen, Jun;Fu, Yun;Zhang, Ruo-Yi;Zhang, Ji;Chen, Shan-Yong;Yu, Xiao-Qi. And the article was included in Tetrahedron in 2011.Reference of 73387-46-9 This article mentions the following:

A simple, highly efficient, and environmentally friendly method for the synthesis of substituted 1H-pyrazoles by one-pot condensation reaction of α,β-unsaturated carbonyl compounds with tosyl hydrazide in water was developed. The reaction system exhibited tolerance with various functional groups. Aromatic moieties with both electron-rich and electron-deficient substituents gave desired products in good to excellent yields. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Reference 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–donor 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.Reference of 73387-46-9

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

Copper-Catalyzed Hydroamination of Oxa- and Azabenzonorbornadienes with Pyrazoles was written by Kim, Kundo;Lee, Yunmi. And the article was included in Journal of Organic Chemistry in 2022.Application In Synthesis of 3-(4-Bromophenyl)-1H-pyrazole This article mentions the following:

An efficient and highly chemo- and stereoselective copper-catalyzed hydroamination of oxa- and azabenzonorbornadienes with various pyrazole derivatives is described. This catalytic process is promoted by the presence of N-heterocyclic carbene ligands and KOt-Bu under mild and simple reaction conditions, and allows for the direct synthesis of new and versatile functionalized oxa(aza)benzonorbornyl pyrazoles I (R = H, 6,7-(OMe)₂, 6,7-(Br)₂, etc; X = O, N(Boc), N(Ac), etc.; R¹ = H, 4-Me, 4-Cl, etc.) starting from readily available oxa(aza)bicyclic alkenes. The synthetic utility of this method was demonstrated by the transformation of the obtained products into pyrazolyl-substituted naphthalenes. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Application In Synthesis of 3-(4-Bromophenyl)-1H-pyrazole).

3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological 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.Application In Synthesis of 3-(4-Bromophenyl)-1H-pyrazole

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

Sulfanilamidopyrazoles. IX. Chloro, methyl, and methoxy derivatives of 1-phenyl-5-sulfanilamidopyrazole was written by Alberti, Carlo;Tironi, C.. And the article was included in Farmaco, Edizione Scientifica in 1967.Application of 14678-93-4 This article mentions the following:

Pyrazoles of the general formula I are prepared; the introduction of Cl, Me, or MeO into the 1-phenyl ring decreases the bacteriostatic activity of I (R = X = H, Ar = p-H2NC6H4SO2) against Staphylococcus aureus and Escherichia coli. Thus, 2.9 g. o-ClC6H4NHNH2 in 10 ml. EtOH is treated with 3.4 g. EtOCH:C(CO2Et)CN in 10 ml. EtOH to give 65% Et α-cyano-β-[2-(o-chlorophenyl)hydrazino]acrylate (II), m. 147-8° (EtOH). Similarly prepared are (m.p. and % yield given): o-MeC6H4NHNHCH:C(CO2Et)CN, 147-8° (C6H6), 90; o-MeOC6H4NHNHCH:C(CO2Et)CN, 118-19° (C6H6), 61. A solution of 5.3 g. II in 50 ml. HOAc is refluxed 3 hrs. to give 80% Et 5-amino-1-(o-chlorophenyl)pyrazole-4-carboxylate, m. 83-4° (C6H6). Similarly prepared are (m.p. given): I (Ar = H, X = o-Me, R = CO2Et), 58-9° (EtOH-water); I (Ar = H, X = o-MeO, R = CO2Et), 78-9° (ligroine). A solution of 16.9 g. EtOCH:C(CO2Et)CN and 14.25 g. m-ClC6H4NHNH2 in 100 ml. EtOH is refluxed 3 hrs. to give 96% I (Ar = H, X = m-Cl, R = CO2Et), m. 117-18° (EtOH). Similarly prepared are the following I (Ar = H, R = CO2Et) (X and m.p. given): p-Cl, 148-9° (EtOH); m-Me, 65-6° (C6H6); p-Me, 114-15° (C6H6); m-MeO, 71-2° (ligroine); p-MeO, 110-11° (ligroine). The I (R = CO2Et) are heated with 2N NaOH to give the following I (Ar = H, R = CO2H) (X and m.p. given): o-Cl, 170-1°; m-Cl, 152-3°; p-Cl, 192-3°; o-Me, 167-8°; m-Me, 169-70°; p-Me, 178-9°; o-MeO, 154-5°; m-MeO, 166-7°; p-MeO, 184-5°. I (Ar = H, R = CO2H, X = o-Me) (4.4 g.) is heated at 170-80° to give 95% 1-(o-tolyl)-5-aminopyrazole, m. 57-8° (C6H6). Similarly prepared are the following I (Ar = R = H) (X and m.p. given): p-Me, 53-4° (ligroine); o-MeO, [HCl salt m. 216-17° (EtOH-Et2O)]; m-MeO, 65-6°; p-MeO, 87-8°. A mixture of 4.75 g. I (Ar = H, R = CO2H, X = o-Cl) and 70 ml. 75% H2SO4 is heated at 150-60° to give 78% I (Ar = R = H, X = o-Cl) (III), m. 56-7° (ligroine-ether); HOAc can also be used. Similarly prepared are the following I (Ar = R = H) (X and m.p. given): m-Cl, 91-2°; p-Cl, 82-3° (ligroine); m-Me, [HCl salt m. 217-18° (EtOH-Et2O)]. A mixture of 3.8 g. III, 4.7 g. p-AcNHC6H4SO2Cl, and 10 ml. pyridine is heated 15 min. at 40-50° and kept 12 hrs. at room temperature to give 90% 1-(o-chlorophenyl)-5-(p-acetamidobenzenesulfonamido)pyrazole (IV), m. 238-9° (dilute EtOH). Similarly prepared are the following I (Ar = p-AcNHC6H4SO2, R = H) (X and m.p. given): p-Cl, 244-5°; o-Me, 237-8°; m-Me, 209-10°; p-Me, 257-8°; o-MeO, 210-11°; m-MeO, 181-2°; p-MeO, 230-1°. A mixture of 3.9 g. IV and 40 ml. 5% NaOH is refluxed to give 87% 1-(o-chlorophenyl)-5-sulfanilamidopyrazole, m. 145-6°. Similarly prepared are the following I (Ar = p-H2NC6H4SO2, R = H) (X and m.p. given): m-Cl, 139-40°; p-Cl, 164-5°; o-Me, 166-7°; m-Me, 123-4°; p-Me, 161-2°; o-MeO, 161-2°; m-MeO, 178-9°; p-MeO, 162-3°. Phenylhydrazines are treated with mixtures of Ac2O and acrylonitrile, N1-phenyl-N2-(2-cyanoethyl)hydrazines are not obtained; the following compounds are isolated (m.p. given): o-ClC6H4NHNHAc, 119-20°; m-ClC6H4NHNHAc, 133-4°; p-ClC6H4NHNHAc, 156-7°. In the experiment, the researchers used many compounds, for example, 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4Application of 14678-93-4).

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4) 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.Application of 14678-93-4

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

Synthesis and biological activity of novel Pyrazolo[3,4-d]pyrimidin-4-one derivatives as potent antifungal agent was written by Wang, Wei;Cheng, Xiang;Cui, Xue;Xia, Dongguo;Wang, Ziqing;Lv, Xianhai. And the article was included in Pest Management Science in 2021.Synthetic Route of C11H11N3O2 This article mentions the following:

To promote the discovery and development of new fungicide with novel scaffolds or modes of action, a series of novel 5-(2-chloroethyl)-1-phenyl-6-(pyridin-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one derivatives I [R¹ = pyridin-3-yl, pyridin-4-yl, 2-chloropyridin-3-yl, etc.; R² = H, Me, F, Cl; R³ = H, Me] were synthesized and evaluated for their antifungal activities. The bioassay data showed that compound I [R¹ = 6-chloropyridin-3-yl, R² = Cl, R³ = H] (EC₅₀ = 1.93 mg L^-1) was superior to boscalid (EC₅₀ = 6.71 mg L^-1) against Valsa mali. Chiral groups was introduced on the structure of cmpnd. I [R¹ = 6-chloropyridin-3-yl, R² = Cl, R³ = H] and two chiral configurations were resp. synthesized, which were (R/S) I [R¹ = 2-chloropyridin-3-yl, R² = Cl, R³ = Me]. Surprisingly, cmpnd. (S) I [R¹ = 2-chloropyridin-3-yl, R² = Cl, R³ = Me] showed significant antifungal activities against Valsa mali and Physalospora piricola with EC₅₀ values of 0.22 and 0.55 mg L^-1. Physiol. and biochem. studies showed that the primary action mechanism of compound (S) I [R¹ = 2-chloropyridin-3-yl, R² = Cl, R³ = Me] on Valsa mali may involve changing mycelial morphol. and increasing cell membrane permeability. These results demonstrated that cmpnd. (S) I [R¹ = 2-chloropyridin-3-yl, R² = Cl, R³ = Me] was modified as fungicide and provided a valuable reference for antifungal agents with pyrazolo[3,4-d]pyrimidin-4-one skeleton. In the experiment, the researchers used many compounds, for example, 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4Synthetic Route of C11H11N3O2).

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4) 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. 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 C11H11N3O2

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

Enaminone-derived pyrazoles with antimicrobial activity was written by Bhat, Mashooq Ahmad;Al-Omar, Mohamed A.;Naglah, Ahmed M.;Khan, Abdul Arif. And the article was included in Journal of Chemistry in 2019.Recommanded Product: 73387-46-9 This article mentions the following:

A series of pyrazoles I [R = 4-methoxy, 4-bromo, 4-morpholino, etc.; R¹ = H, 2-phenylacetyl] derived from the substituted enaminones were synthesized and were evaluated for antimicrobial activity. All the compounds were characterized by the spectral data and elemental anal. Thesynthesized compounds were initially screened for their antimicrobial activity against ATCC 6538, NCTC 10400, NCTC 10418 and ATCC 27853. During initial screening, compounds I [R = 2,4,6-trimethoxy; R¹ = H, R = 2,4-dimethoxy; R¹ = H, R = 4-bromo; R¹ = H] presented significant antimicrobial activity through disk diffusion assay. These compounds were further evaluated for antimicrobial activity at different time points against Gram-pos. and Gram-neg. bacteria and presented significant activity for 6h. The activity was found to be greater against Gram-pos. bacteria. In contrast at 24h, the activity was found only against Gram-pos. bacteria except compound I [R = 4-bromo; R¹ = H], showing activity against both types of bacteria. Compound I [R = 4-bromo; R¹ = H] was found to have highest activity against both Gram-pos. and Gram-neg. bacteria. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Recommanded Product: 73387-46-9).

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

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

Chemoselective Reduction of α-Cyano Carbonyl Compounds: Application to the Preparation of Heterocycles was written by Pollack, Scott R.;Kuethe, Jeffrey T.. And the article was included in Organic Letters in 2016.Quality Control of 3-(4-Bromophenyl)-1H-pyrazole This article mentions the following:

β-Aminoacrylates are reactive intermediates that are useful building blocks in synthesis. General methods for their preparation typically afford α and β disubstitution patterns or β only. Mols. with only α-substituents (β-hydrogen) are much less well-known. A chemoselective reductive tautomerization of α-cyanoacetates, using DIBAL-H, has been developed to access these valuable synthons. α,β-Unsaturated cyanoacetates and α-cyanoketones can, also, be selectively reduced via this methodol. A series of heterocycles were prepared using these β-enamino carbonyl compounds In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Quality Control of 3-(4-Bromophenyl)-1H-pyrazole).

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

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

Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N-Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles was written by Yi, Fanhua;Zhao, Wanjun;Wang, Zikun;Bi, Xihe. And the article was included in Organic Letters in 2019.Recommanded Product: 73387-46-9 This article mentions the following:

A silver-mediated [3 + 2] cycloaddition of “CNN” and “CC” for constructing pyrazoles has been described. The “CNN” building block used is N-isocyanoiminotriphenylphosphorane, which is a stable, safe, easy-to-handle, and odorless solid isocyanide. The reaction is characterized by its mild conditions, broad substrate scope, and excellent functional group tolerance. In the experiment, the researchers used many compounds, for example, 3-(4-Bromophenyl)-1H-pyrazole (cas: 73387-46-9Recommanded Product: 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. 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. Recommanded Product: 73387-46-9

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

Discovery of novel multi-substituted benzo-indole pyrazole Schiff base derivatives with antibacterial activity targeting DNA gyrase was written by Liu, Hao;Chu, Zhi-Wen;Xia, Dong-Guo;Cao, Hai-Qun;Lv, Xian-Hai. And the article was included in Bioorganic Chemistry in 2020.Computed Properties of C11H11N3O2 This article mentions the following:

The design and synthesis of novel multi-substituted benzo-indole pyrazole Schiff base derivatives I (R¹ = H, F, Cl, Me, MeO, Br; R² = H, F, Cl, Me; R³ = CN, COOH) of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds I were examined for their antibacterial activities against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli, and Salmonella. In addition, 20 compounds were selected for the in vitro antibacterial activities assay of 6 drug-resistant bacteria strains. The result revealed compound I (R¹ = Br, R² = Cl, R³ = CN) exhibited excellent antibacterial activity against 4 drug-resistant E. coli bacteria strains with IC₅₀ values of 7.0, 17.0, 13.5, and 1.0μM, resp. In vitro enzyme inhibitory assay showed that compound I (R¹ = Br, R² = Cl, R³ = CN) displayed potent inhibition against DNA gyrase with IC₅₀ values of 0.10μM. The mol. docking model indicated that compounds I (R¹ = Br, R² = Cl, R³ = CN) can bind well to the DNA gyrase by interacting with various amino acid residues. This study demonstrated that the compound I (R¹ = Br, R² = Cl, R³ = CN) can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the com. DNA gyrase inhibiting bactericides. In the experiment, the researchers used many compounds, for example, 5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4Computed Properties of C11H11N3O2).

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carboxylic acid (cas: 14678-93-4) 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. 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. Computed Properties of C11H11N3O2

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

An Efficient Synthesis of Isoxazoles and Pyrazoles under Ultrasound Irradiation was written by Huang, Zhi-Bin;Li, Li-Li;Zhao, Yan-Wei;Wang, Hui-Yuan;Shi, Da-Qing. And the article was included in Journal of Heterocyclic Chemistry in 2014.Formula: C9H7BrN2 This article mentions the following:

A series of 5-arylisoxazoles I (Ar = 4-ClC₆H₄, 4-CH₃C₆H₄, 1-naphthyl, etc.; R= H, Me) and 5-aryl-1H-pyrazole derivatives II were synthesized by the reaction of 3-(dimethylamino)-1-arylprop-2-en-1-ones with hydroxylamine hydrochloride or hydrazine hydrate under ultrasound irradiation without using any catalyst. This method has the advantages of easier work-up, mild reaction condition, high yields, shorter reaction time, and environmentally benign procedure. 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. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Formula: C9H7BrN2

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