Tag: 200-300

Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles was written by Antilla, Jon C.;Baskin, Jeremy M.;Barder, Timothy E.;Buchwald, Stephen L.. And the article was included in Journal of Organic Chemistry in 2004.Application In Synthesis of Ethyl 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate The following contents are mentioned in the article:

A copper-catalyzed N-arylation reaction of π-excessive nitrogen heterocycles is presented. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions that tolerate functional groups such as aldehydes, ketones, alcs., primary amines, and nitriles on the aryl halide or heterocycle, were found. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein. This study involved multiple reactions and reactants, such as Ethyl 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (cas: 741717-60-2Application In Synthesis of Ethyl 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate).

Ethyl 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate (cas: 741717-60-2) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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. Application In Synthesis of Ethyl 1-(pyridin-3-yl)-1H-pyrazole-4-carboxylate

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

‘One-pot’ synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates via lithium tert-butoxide-mediated sterically hindered Claisen condensation and Knorr reaction was written by Jiang, Jian-An;Huang, Wei-Bin;Zhai, Jiao-Jiao;Liu, Hong-Wei;Cai, Qi;Xu, Liu-Xin;Wang, Wei;Ji, Ya-Fei. And the article was included in Tetrahedron in 2013.Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

A concise ‘one-pot’ synthesis of a variety of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates has been developed in moderate to good yields with excellent regioselectivity. Less cost lithium tert-butoxide has been identified as a base for sterically hindered Claisen condensation to efficiently generate the labile 3-substituted 4-aryl-2,4-diketoesters. Furthermore, extensive studies lead to a ‘one-pot’ process by combination of the Claisen condensation and the Knorr reaction for the synthesis of highly valuable 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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.Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

Novel antiobesity agents: Synthesis and pharmacological evaluation of analogues of Rimonabant and of LH21 was written by Alvarado, Mario;Decara, Juan;Luque, Maria Jesus;Hernandez-Folgado, Laura;Gomez-Canas, Maria;Gomez-Ruiz, Maria;Fernandez-Ruiz, Javier;Elguero, Jose;Jagerovic, Nadine;Serrano, Antonia;Goya, Pilar;de Fonseca, Fernando Rodriguez. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

Searching for novel antiobesity agents, a series of cannabinoid LH21 and of Rimonabant-fatty acid amide analogs have been prepared Synthesis of pyrazole analogs was achieved by a two steps simple methodol. via α,β-unsaturated ketones. Carboxamides were obtained in good yields from esters derivatives by a one-pot procedure which takes place under mild conditions. New compounds have been evaluated in vivo as anorectic agents. Some of them showed interesting properties reducing food intake in rats by a mechanism which does not involve the endocannabinoid system. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

Radical Addition of Hydrazones by α-Bromo Ketones To Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis was written by Fan, Xiu-Wei;Lei, Tao;Zhou, Chao;Meng, Qing-Yuan;Chen, Bin;Tung, Chen-Ho;Wu, Li-Zhu. And the article was included in Journal of Organic Chemistry in 2016.Synthetic Route of C18H16N2O2 The following contents are mentioned in the article:

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramol. cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Synthetic Route of C18H16N2O2).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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.Synthetic Route of C18H16N2O2

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

Discovery and evaluation of Ca_v3.1-selective T-type calcium channel blockers was written by Bezencon, Olivier;Remen, Lubos;Richard, Sylvia;Roch, Catherine;Kessler, Melanie;Moon, Richard;Mawet, Jacques;Ertel, Eric A.;Pfeifer, Thomas;Capeleto, Bruno. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Application In Synthesis of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

The authors identified and characterized a series of pyrazole amides as potent, selective Ca_v3.1-blockers. This series culminated with the identification of pyrazole amides (I) and (II), with excellent potencies and/or selectivities toward the Ca_v3.2- and Ca_v3.3-channels. This compound displays poor DMPK properties, making its use difficult for in vivo applications. Nevertheless, this compound as well as analogous ones are well-suited for in vitro studies. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Application In Synthesis of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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 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. Application In Synthesis of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

1,3-Dipolar cycloadditions. XXXIII. Differences in the reactivity of substituted nitrilimines was written by Huisgen, Rolf;Adelsberger, Klaus;Aufderhaar, Ernst;Knupfer, Hans;Wallbillich, Guenter. And the article was included in Monatshefte fuer Chemie in 1967.Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

cf. CA 67: 99380s. Disubstituted nitrilimines (16), released from hydrazide halides with Et3N were compared in their ability to undergo cycloadditions with 12 dipolarophiles of various activities. Electron-attracting substituents on the nitrilimine C and N stabilized the ground state, reduced the 1,3-dipolar activity, and promoted the formation of tetrasubstituted 1,4-dihydro-1,2,4,5-tetrazines (I). At least 3 different reaction paths from hydrazide halides to 1,4-dihydrotetrazines were shown. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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. Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

Pyrazole Linked-1,2,4-Oxadiazole Derivatives as Potential Pharmacological Agent: Design, Synthesis and Antimicrobial Study was written by Kulkarni, Pravin S.;Sarda, Swapnil R.;Khandebharad, Amol U.;Farooqui, Mazahar;Agrawal, Brijmohan R.. And the article was included in Polycyclic Aromatic Compounds.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

A new series of 3-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-5-aryl-1,2,4-oxadiazole I (R = H, 4-Cl, 4-OMe, 3,4-(OMe)₂; R¹ = H, 2-Cl, 4-Cl, 4-Me, 4-OMe, 2,3-(OMe)₂) have been synthesized by a reaction of 5-aryl-N′-hydroxy-1-phenyl-1H-pyrazole-3-carboximidamide with substituted Me benzoate. The newly synthesized compounds I were characterized by spectroscopic techniques and screened for in vitro antibacterial activity against Gram-pos. bacterial strains Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178). Gram-neg. bacterial strains Escherichia coli (NCIM 2574), it was noticed that compounds I (R = 4-Cl; R¹ = 2-Cl, 4-Cl, 4-Me) showed good activity against B. subtilis with MIC 31.25 μg/mL against standard S. albus having MIC 7.81 μg/mL. Proteus mirabilis (NCIM 2388) and in vitro antifungal activity against Aspergillus niger (ATCC 504) Candida albicans (NCIM 3100). Compounds I (R, R¹ = H), I (R = H, R¹ = 2-Cl), I(R = H, R¹ = 4-Me), and I (R = 4-Cl, R¹ = 4-OCH₃) showed good activity against A. niger with MIC 31.25 μg/mL, which are comparable to standard drug ravuconazole having MIC 31.5 μg/mL. Compounds I (R = 4-Cl, R¹ = 2-Cl) and I (R = 4-Cl, R¹ = 4-CH₃) showed activity against A. niger with MIC 7.81 μg/mL which is comparable to standard drug Fluconazole having MIC 7.81 μg/mL and fourfold more activity with respect to drug Ravuconazole. The antibacterial activity of compounds I led to the conclusion that these scaffolds could aid in the creation of lead drugs to treat microbial infection. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

Synthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids was written by Ivachtchenko, Alexandre V.;Kravchenko, Dmitry V.;Zheludeva, Valentina I.;Pershin, Dmitry G.. And the article was included in Journal of Heterocyclic Chemistry in 2004.Reference of 847818-76-2 The following contents are mentioned in the article:

1-Substituted pyrazolylboronic acids and their pinacol esters were prepared by lithiation-borylation reaction sequence starting from bromopyrazoles. Alkylation of 4-bromo-1H-pyrazole gave 1-alkyl-4-bromo-1H-pyrazoles, which were lithiated at -80° and borylated with B(OMe)₃ to give 1-R-1H-pyrazole-4-boronic acids [4a–g, R = Me, Et, Pr, (CH₂)₂CHMe₂, (CH₂)₂OMe, (CH₂)₃NMe₂, (CH₂)₂CH(OEt)₂]. Lithiation of 4-bromo-1-(2-dimethylaminoethyl)-1H-pyrazole (2h) gave 5-lithio-derivative, which on borylation afforded 1-R¹-4-Br-1H-pyrazole-5-boronic acid (8). Boronic acids 4a–g are unstable and were deborylated slowly due to hydrolysis by traces of water; the stability of boryl derivatives can be greatly enhanced by converting to corresponding pinacol boronates (10a–g). Direct lithiation of 1-R²-1H-pyrazoles by BuLi at -20° afforded 5-lithio-derivatives, which were converted to corresponding 1-R²-1H-pyrazole-5-boronic acids [17a–e; R² = Me, ⁱBu, Pr, (CH₂)₂CHMe₂, (CH₂)₂CH(OEt)₂] and their pinacol boronates (18a–e, same R²). The key step in the described methodol. is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis. This study involved multiple reactions and reactants, such as 1-Propyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (cas: 847818-76-2Reference of 847818-76-2).

1-Propyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (cas: 847818-76-2) 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.Reference of 847818-76-2

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

Transformation of 3-isoxazolecarboxylic acids into pyrazole derivatives. IV was written by Cusmano, Sigismondo. And the article was included in Gazzetta Chimica Italiana in 1940.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

cf. C. A. 34, 7903.8. The transformation of 3-isoxazolecarboxylic acids into pyrazolonimines by fusion with PhNHNH₂ may proceed by decarboxylation followed by ring closure of the resulting cyano ketone phenylhydrazone. To test this hypothesis the fusion was repeated in the presence of Natur Kupfer C (I) (or ordinary reduced Cu) so that, at the lower decarboxylation temperatures it might be possible to isolate the phenylhydrazone prior to ring closure and so shed some light on the mechanism of the reaction. A mixture of 1 g. of 5-phenyl-3-isoxazolecarboxylic acid (II), 1 g. I and 1 g. PhNHNH₂ in 20 cc. alc. was boiled for a few min. over a free flame, filtered, alkalinized with Na₂CO₃, extracted free from PhNHNH₂ with ether, acidified with dilute H₂SO₄, and extracted with ether. The residue from the evaporated extract gave 1,5-diphenyl-3-pyrazolecarboxylic acid (III), m. 185° (Et ester, m. 98°), decarboxylated by fusion to give 1,5-diphenylpyrazole, m. 55°, and identical with the known acid prepared by the action of PhNHNH₂ on BzCH₂COCO₂H. A similar transformation of 5-methyl-3-isoxazolecarboxylic acid (IV) gave 1-phenyl-5-methyl-3-pyrazolecarboxylic acid, m. 136° (Me ester, m. 55°), decarboxylated to 1-phenyl-5-methylpyrazole, transformed into the known picrate, m. 98°. In these transformations alc. can be replaced by other solvents. In the absence of I or in the presence of PhNH₂ instead of PhNHNH₂ the isoxazolecarboxylic acid is recovered unchanged. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

Discovery of 1,5-Diphenylpyrazole-3-Carboxamide Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors was written by Aghazadeh-Tabrizi, Mojgan;Baraldi, Pier Giovanni;Baraldi, Stefania;Ruggiero, Emanuela;De Stefano, Lucia;Rizzolio, Flavio;Di Cesare Mannelli, Lorenzo;Ghelardini, Carla;Chicca, Andrea;Lapillo, Margherita;Gertsch, Jurg;Manera, Clementina;Macchia, Marco;Martinelli, Adriano;Granchi, Carlotta;Minutolo, Filippo;Tuccinardi, Tiziano. And the article was included in Journal of Medicinal Chemistry in 2018.COA of Formula: C18H16N2O2 The following contents are mentioned in the article:

Monoacylglycerol lipase (MAGL) is a serine hydrolase that plays an important role in the degradation of the endocannabinoid neurotransmitter 2-arachidonoylglycerol, which is implicated in many physiol. processes. Beyond the possible utilization of MAGL inhibitors as anti-inflammatory, antinociceptive, and anticancer agents, their application has encountered obstacles due to the unwanted effects caused by the irreversible inhibition of this enzyme. The possible application of reversible MAGL inhibitors has only recently been explored, mainly due to the deficiency of known compounds possessing efficient reversible inhibitory activities. The authors report a new series of reversible MAGL inhibitors. Among them, compound 26 ((4-benzylpiperidin-1-yl)(5-(4-hydroxyphenyl)-1-(3-methylbenzyl)-1H-pyrazol-3-yl)methanone) showed to be a potent MAGL inhibitor (IC₅₀ = 0.51 μM, K_i = 412 nM) with a good selectivity vs. fatty acid amide hydrolase (FAAH), α/β-hydrolase domain-containing 6 (ABHD6), and 12 (ABHD12). Interestingly, this compound also possesses antiproliferative activities against two different cancer cell lines and relieves the neuropathic hypersensitivity induced in vivo by oxaliplatin. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8COA of Formula: C18H16N2O2).

Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8) 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 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.COA of Formula: C18H16N2O2

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