Day: November 22, 2022

Synthesis and biological screening of novel 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole derivatives was written by Kulkarni, Pravin S.;Sarda, Swapnil R.;Khandebharad, Amol U.;Farooqui, Mazahar;Agrawal, Brijmohan R.. And the article was included in Asian Journal of Chemistry in 2022.Reference of 17355-75-8 The following contents are mentioned in the article:

A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole I [R = H, 4-Cl, 3,4-(OCH₃)₂; R¹ = H, 4-F, 2-CH₃, 3-CH₃, 4-CH₃] have been synthesized by a cyclocondensation reaction of Et 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate II with aryl imidoxime R¹C₆H₄C(=NOH)NH₂. The newly synthesized pyrazolyl-1,2,4-oxadiazole derivatives I were characterized by spectroscopic techniques and screened for in vitro antibacterial activity against Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178), Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) and in vitro antifungal activity against Aspergillus niger (ATCC 504) Candida albicans (NCIM 3100). This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8Reference of 17355-75-8).

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.Reference of 17355-75-8

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

Structural examination of halogen-bonded co-crystals of tritopic acceptors was written by Andree, Stefan N. L.;Sinha, Abhijeet S.;Aakeroy, Christer B.. And the article was included in Molecules in 2018.Application of 172606-26-7 The following contents are mentioned in the article:

A series of tritopic N-heterocyclic compounds containing electrostatically and geometrically equivalent binding sites were synthesized and subjected to systematic co-crystallizations with selected perfluoroiodoarenes in order to map out their structural landscapes. More than 70% of the attempted reactions produced a co-crystal as indicated by IR spectroscopy. Four new crystal structures were reported and in all of them, at least one potential binding site on the acceptor was left vacant. The absence of halogen bonds to all sites was ascribed primarily due to deactivation of the σ-hole on the iodo-arene donors and partially due to steric hindrance. The tritopic acceptors containing 5,6-dimethylbenzimidazole derivatives yield discrete tetrameric aggregates in the solid state, whereas the pyrazole and imidazole analogs assemble into halogen-bonded 1-D chains. This study involved multiple reactions and reactants, such as 1,1′,1”-((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(1H-pyrazole) (cas: 172606-26-7Application of 172606-26-7).

1,1′,1”-((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(1H-pyrazole) (cas: 172606-26-7) 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. 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.Application of 172606-26-7

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

Synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine was written by Bai, Zhong-Gang;Qi, Hui;Zhang, Qun-Zheng;Ma, Yu;Pan, Qing;Zhang, Xun-Li. And the article was included in Heterocycles in 2017.Recommanded Product: 1260672-10-3 The following contents are mentioned in the article:

This short paper reports the development of a new method for the synthesis of (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine. Pyrazole was initially N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group, followed by alkylation at C-5 position with 1-bromo-3-chloropropane. Following SEM deprotection, the intramol. ring was closed and then a bromine atom (Br) was introduced with N-bromosuccinimide (NBS) by electrophilic aromatic substitution (S_EAr), forming 3-bromo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole. The Br group was subsequently converted into aldehyde group, then into oxime. The final step of hydrogenation resulted in the desired product. The overall yield through the 8-step reaction process was found to be 29.4%. This development provides a novel synthetic route to the formation of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole skeleton. This study involved multiple reactions and reactants, such as (5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine (cas: 1260672-10-3Recommanded Product: 1260672-10-3).

(5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)methanamine (cas: 1260672-10-3) 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 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.Recommanded Product: 1260672-10-3

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

Phosphodiesterase inhibitors. Part 4: Design, synthesis and structure-activity relationships of dual PDE3/4-inhibitory fused bicyclic heteroaromatic-4,4-dimethylpyrazolones was written by Ochiai, Koji;Takita, Satoshi;Kojima, Akihiko;Eiraku, Tomohiko;Ando, Naoki;Iwase, Kazuhiko;Kishi, Tetsuya;Ohinata, Akira;Yageta, Yuichi;Yasue, Tokutaro;Adams, David R.;Kohno, Yasushi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Related Products of 141032-72-6 The following contents are mentioned in the article:

(-)-6-(7-Methoxy-2-trifluoromethylpyrazolo[1,5-a]pyridin-4-yl)-5-methyl-4,5-dihydro-3-(2H)-pyridazinone (KCA-1490) is a dual PDE3/4 inhibitor that exhibits potent combined bronchodilatory and anti-inflammatory activity. Here we show that a 4,4-dimethylpyrazolone subunit serves as an effective surrogate for the 5-methyl-4,5-dihydropyridazin-3(2H)-one ring of KCA-1490 while lacking a stereogenic center. The 2- and 7-substituents in the pyrazolo[1,5-a]pyridine subunit markedly influence the PDE-inhibitory profile and can be adjusted to afford either potent PDE4-selective inhibitors or dual PDE3/4 inhibitors. A survey of bicyclic heteroaromatic replacements for the pyrazolo[1,5-a]pyridine allowed further refinement of the inhibitory profile and identified 3-(8-methoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-5-yl)-4,4-dimethyl-1H-pyrazol-5(4H)-one as an orally active, achiral KCA-1490 analog with well-balanced dual PDE3/4-inhibitory activity. This study involved multiple reactions and reactants, such as Pyrazolo[1,5-a]pyridin-4-ol (cas: 141032-72-6Related Products of 141032-72-6).

Pyrazolo[1,5-a]pyridin-4-ol (cas: 141032-72-6) 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.Related Products of 141032-72-6

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

Similarity in physical organic chemistry: substituent effects on the intrinsic basicity of 4-substituted pyrazoles was written by Notario, R.;Herreros, M.;El Hammadi, A.;Homan, H.;Abboud, J.-L. M.;Forfar, I.;Claramunt, R. M.;Elguero, J.. And the article was included in Journal of Physical Organic Chemistry in 1994.Application In Synthesis of 2,2,2-Trifluoro-1-(1H-pyrazol-4-yl)ethanone The following contents are mentioned in the article:

The gas-phase basicities of eight pyrazoles substituted only at position 4 (R = H, NO₂, F, Cl, CO₂C₂H₅, CH₃, NH₂, 1-adamantyl) were measured by Fourier transform ion cyclotron resonance. The exptl. values were treated in two ways, first by comparing these values with the AM1-calculated proton affinities. Since the correlation was reasonably good [PA(calculate) = -11.3 + 1.0634PA(exp.), n = 8, r = 0.984], a set of 17 further 4-substituted pyrazoles and their cations were calculated using the AM1 approximation and their gas-phase basicities were estimated Second, both the exptl. and the AM1-calculated values were considered within the framework of the Taft-Topsom anal. of substituent effects. Comparison of the analyses for pyrazoles and pyridines led to the unexpected result that, in spite of differences in ring size and number of heteroatoms, both systems behave remarkably alike. This study involved multiple reactions and reactants, such as 2,2,2-Trifluoro-1-(1H-pyrazol-4-yl)ethanone (cas: 161957-47-7Application In Synthesis of 2,2,2-Trifluoro-1-(1H-pyrazol-4-yl)ethanone).

2,2,2-Trifluoro-1-(1H-pyrazol-4-yl)ethanone (cas: 161957-47-7) 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. Application In Synthesis of 2,2,2-Trifluoro-1-(1H-pyrazol-4-yl)ethanone

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

Direct-to-Biology Accelerates PROTAC Synthesis and the Evaluation of Linker Effects on Permeability and Degradation was written by Hendrick, Charles E.;Jorgensen, Jeff R.;Chaudhry, Charu;Strambeanu, Iulia I.;Brazeau, Jean-Francois;Schiffer, Jamie;Shi, Zhicai;Venable, Jennifer D.;Wolkenberg, Scott E.. And the article was included in ACS Medicinal Chemistry Letters in 2022.Computed Properties of C12H20N4O2 The following contents are mentioned in the article:

A platform to accelerate optimization of proteolysis targeting chimeras (PROTACs) had been developed using a direct-to-biol. (D2B) approach with a focus on linker effects. A large number of linker analogs-varying length, polarity, and rigidity-were rapidly prepared and characterized in four cell-based assays by streamlining time-consuming steps in synthesis and purification The expansive data set informs on linker structure activity relationships for in-cell E3 ligase target engagement, degradation, permeability, and cell toxicity. Unexpected aspects of linker SAR were discovered, consistent with literature reports on “linkerol.”, and the method dramatically speeds up empirical optimization. Physicochem. property trends emerged, and the platform had the potential to rapidly expand training sets for more complex prediction models. In-depth validation studies were carried out and confirm the D2B platform was a valuable tool to accelerate PROTAC design-make-test cycles. This study involved multiple reactions and reactants, such as tert-Butyl 3-(aminomethyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (cas: 1251000-58-4Computed Properties of C12H20N4O2).

tert-Butyl 3-(aminomethyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (cas: 1251000-58-4) belongs to pyrazole derivatives. The strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Computed Properties of C12H20N4O2

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

Palladium-Catalyzed Chelation-Assisted Regioselective Oxidative Dehydrogenative Homocoupling/Ortho-Hydroxylation in N-Phenylpyrazoles was written by Batchu, Harikrishna;Bhattacharyya, Soumya;Kant, Ruchir;Batra, Sanjay. And the article was included in Journal of Organic Chemistry in 2015.HPLC of Formula: 17355-75-8 The following contents are mentioned in the article:

A palladium-catalyzed pyrazole-directed regioselective oxidative C(sp2)-H functionalization of the N-Ph ring in N-phenylpyrazoles to afford either a biaryl bis-pyrazole I [R¹ = H, Me, Ph, and CO₂Et; R² = H, CO₂Et; R³ = H, Me, Pr, etc.; R = H, Me, Cl, etc.] (via dehydrogenative homocoupling) or N-(o-hydroxyphenyl)pyrazole II [R¹ = H, Me, Ph, and CO₂Et; R² = H, CO₂Et; R³ = H, Me, Pr, etc.; R = H, Me, Cl, etc.] (via C-H oxygenation) or their mixture is described. The substitutions on the N-Ph ring and the pyrazole ring and the dilution of the reaction medium with respect to the TFA/TFAA mixture (substrate concentration) have a remarkable influence on the outcome of the reaction. It was discovered that if the reactions were performed under highly dilute conditions (ca. 10 times) then N-(o-hydroxyphenyl)pyrazoles were the major or the sole products. This study involved multiple reactions and reactants, such as Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate (cas: 17355-75-8HPLC of Formula: 17355-75-8).

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. 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. HPLC of Formula: 17355-75-8

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

Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors was written by Shcherbakov, Dmitriy;Baev, Dmitriy;Kalinin, Mikhail;Dalinger, Alexander;Chirkova, Varvara;Belenkaya, Svetlana;Khvostov, Aleksei;Krut’ko, Dmitry;Medved’ko, Aleksei;Volosnikova, Ekaterina;Sharlaeva, Elena;Shanshin, Daniil;Tolstikova, Tatyana;Yarovaya, Olga;Maksyutov, Rinat;Salakhutdinov, Nariman;Vatsadze, Sergey. And the article was included in ACS Medicinal Chemistry Letters in 2022.Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

For the first time, derivatives of 3,7-diazabicyclo[3.3.1]nonane (bispidine) were proposed as potential inhibitors of the SARS-CoV-2 main viral protease (3-chymotrypsin-like, 3CLpro). Based on the created pharmacophore model of the active site of the protease, a group of compounds were modeled and tested for activity against 3CLpro. The 3CLpro activity was measured using the fluorogenic substrate Dabcyl-VNSTLQSGLRK(FAM)MA; the efficiency of the proposed approach was confirmed by comparison with literature data for ebselen and disulfiram. The results of the experiments performed with bispidine compounds showed that 14 compounds exhibited activity in the concentration range 1-10μM, and 3 samples exhibited submicromolar activity. The structure-activity relationship studies showed that the mols. containing a carbonyl group in the ninth position of the bicycle exhibited the maximum activity. Based on the exptl. and theor. results obtained, further directions for the development of this topic were proposed. 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 strategies for the synthesis of pyrazoles generally can be applied for the construction of indazoles. 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.Quality Control of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate

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

New Pyrazolium-carboxylates as Structural Analogues of the Pseudo-Cross-Conjugated Betainic Alkaloid Nigellicine was written by Schmidt, Andreas;Habeck, Tobias;Kindermann, Markus Karl;Nieger, Martin. And the article was included in Journal of Organic Chemistry in 2003.Safety of Ethyl 1,5-diphenyl-1H-pyrazole-3-carboxylate The following contents are mentioned in the article:

Pyrazolium-3-carboxylates were examined as relatives of the betainic alkaloid nigellicine and as new examples of the sparsely populated class of heterocyclic pseudo-cross-conjugated mesomeric betaines. The title compounds were prepared in a 4-step procedure starting from EtO₂CCOCH:CROH [R = Me, Ph] which were cyclized with substituted hydrazines. The resulting isomeric pyrazole esters were separated and quaternized with di-Me sulfate in the presence of nitrobenzene to pyrazolium esters. Saponification was best accomplished in diluted sulfuric acid, which resulted in the formation of the pseudo-cross-conjugated mesomeric betaines in one step. Protonation to the corresponding carboxylic acids required the treatment of the betaines with tetrafluoroboric acid in dichloromethane. The effect of neg. solvatochromism proves the charge separation in the ground state of the mols. X-ray crystallog. analyses, semiempirical calculations, and ESI mass spectrometric measurements were performed to gain knowledge about the phenomenon of pseudo-cross-conjugation. 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 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 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

Crystalline Ammonium Complexes of Trimethyl- and Triethylbenzene-Based Tripodal Compounds Bearing Pyrazole and Indazole Groups was written by Schulze, Mathias M.;Koch, Niklas;Seichter, Wilhelm;Mazik, Monika. And the article was included in European Journal of Organic Chemistry in 2018.Recommanded Product: 172606-26-7 The following contents are mentioned in the article:

Crystalline complexes of NH₄⁺PF₆^– with trimethyl- and triethylbenzene-based tripodal compounds, bearing either pyrazole or indazole groups, were prepared and characterized by X-ray diffraction studies. The supramol. motifs observed in the crystal structures and the conformations of the tripodal mols. have been the subject of a detailed anal. and are described in this paper. The pyrazole-bearing side arms of the hosts with a trimethylbenzene scaffold are arranged in an aaa fashion and form a cavity including the ammonium ion. In the case of the triethylbenzene derivatives, the fully alternating arrangement of the pyrazole/indazole and Et groups is observed and by taking the Et groups into account, the conformation can be defined as ab’ab’ab’. The conformations observed in the crystals of the free host mols. can be defined as ab’ab’ba’ with the indazole-bearing arms arranged in an aab fashion. The crystal packings of the complexes are, among other things, characterized by the presence of NH···F and CH···F hydrogen bonds as well as by CBr···N and CBr···π halogen bonds in the case of the bromo-substituted derivatives This study involved multiple reactions and reactants, such as 1,1′,1”-((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(1H-pyrazole) (cas: 172606-26-7Recommanded Product: 172606-26-7).

1,1′,1”-((2,4,6-Trimethylbenzene-1,3,5-triyl)tris(methylene))tris(1H-pyrazole) (cas: 172606-26-7) 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. Recommanded Product: 172606-26-7

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