Day: November 22, 2022

Self-Assembly of Ball-Shaped Molecular Complexes in Water was written by Grawe, Thomas;Schrader, Thomas;Zadmard, Reza;Kraft, Arno. And the article was included in Journal of Organic Chemistry in 2002.Reference of 172606-26-7 The following contents are mentioned in the article:

The authors present a simple and versatile access to spheroidal mol. assemblies with pronounced stability in highly polar solvents. These complexes are composed of doubly and triply charged complementary building blocks based on ammonium or amidinium cations and phosphonate anions. Their high thermodn. stability is best explained by the formation of a cyclic array of alternating pos. and neg. charges interconnected by a regular network of H bonds. Association constants reach 10⁶ M^-1 in methanol and often surpass 10³ M^-1 in water. The broad range of binding energies correlates well with the varying degree of preorganization of both complex partners. As a byproduct of these studies, new recognition motifs for histidine and arginine esters and the unsubstituted guanidinium ion are proposed. The addnl. introduction of Me groups in the 2-, 4-, and 6-positions of the central benzene ring in either cations or anions causes a marked drop in the corresponding K_a values of 1 order of magnitude; the related rotational barriers were estimated at 0.3-2.1 kcal/mol. Spontaneous formation of defined 2:1 complexes from three components also was observed 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: 172606-26-7Reference 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. 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. Reference of 172606-26-7

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

Functionally Selective Dopamine D₂, D₃ Receptor Partial Agonists was written by Moeller, Dorothee;Kling, Ralf C.;Skultety, Marika;Leuner, Kristina;Huebner, Harald;Gmeiner, Peter. And the article was included in Journal of Medicinal Chemistry in 2014.Synthetic Route of C7H6N2O The following contents are mentioned in the article:

Dopamine D₂ receptor-promoted activation of Gα_o over Gα_i may increase synaptic plasticity and thereby might improve neg. symptoms of schizophrenia. Heterocyclic dopamine surrogates comprising a pyrazolo[1,5-a]pyridine moiety were synthesized and investigated for their binding properties when low- to subnanomolar K_i values were determined for D_2L, D_2S, and D₃ receptors. Measurement of [³⁵S]GTPγS incorporation at D_2S coexpressed with G-protein subunits indicated significant bias for promotion of Gα_o1 over Gα_i2 coupling for several test compounds Functionally selective D_2S activation was most striking for the carbaldoxime I (Gα_o1, pEC₅₀ = 8.87, E_max = 65%; Gα_i2, pEC₅₀ = 6.63, E_max = 27%). In contrast, the investigated 1,4-disubstituted aromatic piperazines (1,4-DAPs) behaved as antagonists for β-arrestin-2 recruitment, implying significant ligand bias for G-protein activation over β-arrestin-2 recruitment at D_2S receptors. Ligand efficacy and selectivity between D_2S and D₃ activation were strongly influenced by regiochem. and the nature of functional groups attached to the pyrazolo[1,5-a]pyridine moiety. This study involved multiple reactions and reactants, such as Pyrazolo[1,5-a]pyridin-4-ol (cas: 141032-72-6Synthetic Route of C7H6N2O).

Pyrazolo[1,5-a]pyridin-4-ol (cas: 141032-72-6) belongs to pyrazole derivatives. Pyrazole and its derivatives are considered a pharmacologically important active scaffold that possesses almost all types of pharmacological activities. Pyrazoles can be selectively lithiated at different carbons and subsequently react with electrophiles depending on the substitution patterns.Synthetic Route of C7H6N2O

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

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

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