pyrazoles-derivatives

Britton, Luke published the artcileManganese-Catalyzed C(sp²)-H Borylation of Furan and Thiophene Derivatives, Category: pyrazoles-derivatives, the publication is ACS Catalysis (2021), 11(12), 6857-6864, database is CAplus.

Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp²)-H borylation reactions. C(sp²)-H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples using Earth-abundant alternatives have emerged, Mn catalysis remains lacking. The Mn-catalyzed C-H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active Mn hydride species. Mechanistic studies showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp²)-H bond borylation occurs through a C-H metalation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a Mn borohydride complex, which was as an off-cycle resting state.

ACS Catalysis published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Category: pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Gharbaoui, Tawfik published the artcileAgonist lead identification for the high affinity niacin receptor GPR109a, Safety of 3-Isopropyl-1H-pyrazole-5-carboxylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(17), 4914-4919, database is CAplus and MEDLINE.

A strategy for lead identification of new agonists of GPR109a, starting from known compounds shown to activate the receptor, is described. Early compound triage led to the formulation of a binding hypothesis and eventually to our focus on a series of pyrazole acid derivatives Further elaboration of these compounds provided a series of 5,5-fused pyrazoles to be used as lead compounds for further optimization.

Bioorganic & Medicinal Chemistry Letters published new progress about 890590-91-7. 890590-91-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid, name is 3-Isopropyl-1H-pyrazole-5-carboxylic acid, and the molecular formula is C7H10N2O2, Safety of 3-Isopropyl-1H-pyrazole-5-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Sagar, Satish published the artcileStructure activity relationship (SAR) study identifies a quinoxaline urea analog that modulates IKKβ phosphorylation for pancreatic cancer therapy, Application of 1-Methylpyrazole, the publication is European Journal of Medicinal Chemistry (2021), 113579, database is CAplus and MEDLINE.

Genetic models validated Inhibitor of nuclear factor (NF) kappa B kinase beta (IKKβ) as a therapeutic target for KRAS mutation associated pancreatic cancer. Phosphorylation of the activation loop serine residues (S177, S181) in IKKβ is a key event that drives tumor necrosis factor (TNF) α induced NF-κB mediated gene expression. Here we conducted structure activity relationship (SAR) study to improve potency and oral bioavailability of a quinoxaline analog 13-197 that was previously reported as a NFκB inhibitor for pancreatic cancer therapy. The SAR led to the identification of a novel quinoxaline urea analog 84 that reduced the levels of p-IKKβ in dose- and time-dependent studies. When compared to 13-197, analog 84 was âˆ?.5-fold more potent in TNFα-induced NFκB inhibition and âˆ?-fold more potent in inhibiting pancreatic cancer cell growth. Analog 84 exhibited âˆ?.3-fold greater exposure (AUC0-âˆ? resulting in âˆ?.7-fold increase in oral bioavailability (%F) when compared to 13-197. Importantly, oral administration of 84 by itself and in combination of gemcitabine reduced p-IKKβ levels and inhibited pancreatic tumor growth in a xenograft model.

European Journal of Medicinal Chemistry published new progress about 930-36-9. 930-36-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole, name is 1-Methylpyrazole, and the molecular formula is C4H6N2, Application of 1-Methylpyrazole.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Xu, Jing published the artcileMolecular Mechanisms of the Blockage of Glioblastoma Motility, Name: 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide, the publication is Journal of Chemical Information and Modeling (2021), 61(6), 2967-2980, database is CAplus and MEDLINE.

Glioblastoma (GBM) is the most common and lethal brain tumor. GBM has a remarkable degree of motility and is able to infiltrate the healthy brain. In order to perform a rationale-based drug-repositioning study, we have used known inhibitors of two small Rho GTPases, Rac1 and Cdc42, which are upregulated in GBM and are involved in the signaling processes underlying the orchestration of the cytoskeleton and cellular motility. The selected inhibitors (R-ketorolac and ML141 for Cdc42 and R-ketorolac and EHT 1864 for Rac1) have been successfully employed to reduce the infiltration propensity of GBM in live cell imaging studies. Complementarily, all-atom simulations have elucidated the mol. basis of their inhibition mechanism, identifying the binding sites targeted by the inhibitors and dissecting their impact on the small Rho GTPases�function. Our results demonstrate the potential of targeting the Rac1 and Cdc42 proteins with small mols. to contrast GBM infiltration growth and supply precious information for future drug discovery studies aiming to fight GBM and other infiltrative cancer types.

Journal of Chemical Information and Modeling published new progress about 71203-35-5. 71203-35-5 belongs to pyrazoles-derivatives, auxiliary class GPCR/G Protein,Ras, name is 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide, and the molecular formula is C14H26O2, Name: 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Finar, I. L. published the artcileReaction between aroylacetones and arylhydrazines, Formula: C16H12N2O2, the publication is Journal of the Chemical Society (1958), 200-4, database is CAplus.

PhNHNH₂ and ο-, m-, and p-nitrobenzoylacetones react to form only 5-ο-, -m-, and -p-nitrophenyl-3-methyl-1-phenylpyrazoles (I), 3,1,-5-MePh(x-O₂NC₆H₄)C₃HN₂, whereas BzCH₂Ac and 2,4-(O₂N)₂C₆H₃NHNH₂ give both 1-(2,4-dinitrophenyl)-3-methyl-5-phenylpyrazole (II) and 1-(2,4-dinitrophenyl)-5-methyl-3-phenylpyrazole (III). The orientation of I (x = 3 or 4) (IIIa, IIIb) was established by reduction to the amine, diazotization, and treatment with H₃PO₂ to give 3-methyl-1,5-diphenylpyrazole (IV). Similar treatment of I (x = 2) (IVa) gave 3-methyl-1-phenyl-1H-pyrazolo[4,5-c]cinnoline (V) instead of the expected methyldiphenylpyrazole. To prevent the formation of V, IVa was converted into the 4-Br derivative Reduction to the amine, followed by diazotization and treatment of the diazonium salt (VI) with H₃PO₂ gave 4-bromo-3-methylpyrazolo[1,2-d]phenanthridine (VII). Oxidation of IV by boiling with KMnO₄ in dilute C₅H₅N gave authentic 1,5-diphenylpyrazole-3-carboxylic acid. PhNHNH₂ (1.3 g.) and 2.35 g. ο-O₂NC₆H₄COCH₂Ac heated 10 min. in alc. at 35-40° gave 3.17 g. yellow phenylhydrazone (IX), m. 156° (cf. Koenigs and Freund, C.A. 42, 1935h). Heating 10 g. diketone in alc. with 5.4 g. PhNHNH₂ in alc. on a steam bath 5 min. gave 6.4 g. of another form of the phenylhydrazone (IXa), m. 136°, together with 7.5 g. IVa. Colorless IXa boiled in alc. and the solution cooled quickly gave IX. Both IX and IXa heated in alc. on a steam bath or recrystallized from CHCl₃, AcOH, or C₆H₆ slowly formed IVa. PhNHNH₂ (1.2 g.) and 2.3 g. m-O₂NC₆H₄COCH₂Ac refluxed 3 hrs. in alc. yielded 93% IIIa, m. 102-3°. Condensation of p-O₂NC₆H₄COCl with AcCH₂CO₂Et in the presence of NaOMe in MeOH by an adaptation of the method of Bülow and Hailer [Ber. 35, 932(1902)], dilution of the mixture with ice H₂O, filtration, pouring the filtrate into cold AcOH, and extraction with Et₂O yielded 48% p-O₂NC₆H₄COCH₂CO₂Et, converted according to Knorr and Jödicke [Ber. 18, 2259(1885)] to 3-methyl-5-(p-nitrophenyl)-1-phenylpyrazole-4-carboxylic acid (X), m. 210°, and transformed by heating 3 hrs. at 240-50° to IIIb, m. 111-12°, also obtained in 36% yield by refluxing 2.0 g. p-O₂NC₆H₄COCH₂Ac and 1.1 g. PhNHNH₂ in alc. BzCH₂Ac (20 g.) in alc. and 16 g. 2,4-(O₂N)₂C₆H₃NHNH₂ in 32 ml. 98% H₂SO₄ and 350 ml. hot alc. heated 10 min. on a steam bath and the mixture decanted gave 15.3 g. II, m. 137° (alc. or AcOH). The decanted solution cooled and filtered yielded 2.1 g. III, m. 154° (alc. or AcOH). IVa, II, and III in AcOH treated with excess Br at room temperature and filtered, the precipitate taken up in CHCl₃, and the solution washed with aqueous Na₂CO₃ and H₂O gave 86, 93, and 91% of the corresponding 4-Br derivatives m. 141, 176, and 158°, resp. The nitro compounds IIIa, IIIb, and IVa (1 mole) in alc. heated 1 hr. on a steam bath with 8 moles SnCl₂ in concentrated HCl and the cooled solution made alk. with 30% NH₄OH, the amine extracted with Et₂O, and recrystallized (alc.) yielded the corresponding 5-aminophenyl-3-methyl-1-phenylpyrazoles (XI): m-amino (XIa), m. 161.5°; p-amino (XIb), m. 93°; ο-amino (XIc), m. 96°, also obtained as a better product, m. 99°, by heating 17.5 g. IVa in 10 ml. 60% N₂H₄.H₂O in alc. on a steam bath in the presence of 2 g. Pd-C. Similar reduction of 10 g. 4-Br derivative of IVa gave 5.1 g. 5-(ο-aminophenyl)-4-bromo-3-methyl-1-phenylpyrazole (XId), m. 135°. X was converted by the procedure of K. and J. (loc. cit.) to the corresponding 5-(p-aminophenyl)-3-methyl-1-phenylpyrazole-4-carboxylic acid (XIe), m. 261°. II (8 g.) in 500 ml. alc. and 15 ml. 30% NH₄OH saturated with H₂S heated 1 hr. on a steam bath and evaporated, the crystalline product (5.3 g.) taken up in concentrated HCl and filtered, the filtrate diluted with H₂O, and the precipitate crystallized gave 1-(4-amino-2-nitrophenyl)-3-methyl-5-phenylpyrazole (XII), m. 182° (alc.). III (1.4 g.) in 60 ml. alc. and 3 ml. 30% NH₄OH reduced with H₂S yielded 54% 1-(4-amino-2-nitrophenyl)-5-methyl-3-phenylpyrazole, m. 170° (alc. or ligroine). The aminophenylpyrazoles (0.6 g.) in 3 ml. concentrated HCl were diazotized 30 min. with 0.3 g. NaNO₂ in 0.5 ml. H₂O and the solution poured into 7 ml. 30% H₃PO₂. XIa and XIb both gave IV, characterized as its Br derivative m. 75°. XIe gave authentic 3-methyl-1,5-diphenyl-pyrazole-4-carboxylic acid, m. 205°. The product obtained by heating 4-chloroquinaldine with excess PhNHNH₂ in a sealed tube at 200° (K. and F., loc. cit.) was shown to be 3-(ο-aminophenyl)-5-methyl-1-phenylpyrazole (XIII) since it gave 5-methyl-1,3-diphenylpyrazole (picrate, m. 108°). XIc gave V, m. 216°, also obtained when the diazonium salt solution was heated with alc. and Gattermann Cu powder or with boiling 50% H₂SO₄, or was made alk. with NaOH solution XId was similarly converted through the diazonium salt VI to VII, m. 140°. XII gave red needles, m. 108°, by the above procedure but deaminating by addition of 1 g. XII, in 12 ml. AcOH to 0.3 g. NaNO₂ in 1.5 ml. concentrated H₂SO₄ at 5°, keeping the mixture 30 min. at 5°, heating 30 min. on a steam bath with 20 ml. alc., diluting with H₂O, and extracting with Et₂O gave authentic 3-methyl-1-(ο-nitrophenyl)-5-phenylpyrazole, m. 104°. Reduction of the aminophenylpyrazoles with Na and alc. and evaporation, solution in concentrated H₂SO₄, and addition of aqueous NaNO₂ according to the Knorr pyrazoline reaction procedure gave red color with XIa, XIb, XIc, and 1-(ο-aminophenyl)-3-methyl-5-phenylpyrazole (C.A. 51, 7357g), and a blue color with XIII.

Journal of the Chemical Society published new progress about 13599-22-9. 13599-22-9 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Carboxylic acid,Benzene, name is 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, and the molecular formula is C16H12N2O2, Formula: C16H12N2O2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Lyalin, B. V. published the artcileOxidative transformation of N-substituted 3-aminopyrazoles to azopyrazoles using electrogenerated bromine as a mediator, Quality Control of 105675-85-2, the publication is Russian Chemical Bulletin (2018), 67(3), 510-516, database is CAplus.

The one-pot process of anodic transformation of N-alkyl-3-aminopyrazoles into azopyrazoles I [R¹ = H, Me, Et; R² = H, Me; R³ = Br, Me] under conditions of membraneless electrolysis in an aqueous solution of NaBr was studied for the first time. It was found that under these conditions the aminopyrazoles, which do not have a substituent at position 4, transform into the corresponding 4,4′-dibromoazopyrazoles. The corresponding yield was in the interval of 28-80%, depending on the structure of the products. The transformation of 4-substituted aminopyrazoles resulted in the formation of azopyrazoles in the yields lying within 62-86% when this process was implemented under conditions with the anodically generated Br₂ acting as a mediator. A convenient method of anodic synthesis of azopyrazoles in an aqueous medium without the use of additives of chem. oxidants was proposed. The process was environmentally sound and was characterized by a high atom efficiency (>85%).

Russian Chemical Bulletin published new progress about 105675-85-2. 105675-85-2 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Bromide,Amine, name is 4-Bromo-1-methyl-1H-pyrazol-5-amine, and the molecular formula is C4H6BrN3, Quality Control of 105675-85-2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Thiruchelvi, R. published the artcileIn-Silico analysis to identify the potent inhibitor of Rho GTPase activating protein for the usage of the Glaucoma, SDS of cas: 71203-35-5, the publication is Materials Today: Proceedings (2021), 37(Part_2), 1897-1904, database is CAplus.

Considered as the one of the leading irreversible loss of vision causing optic neuropathy, Glaucoma is estimated to hit more than 80 million by the end of 2020 via population survey. Increased intraocular pressure is taken as one of the risk factors among others behind the root of causing the disease. The imbalance in the secretion and the excretion of the aqueous humor inside and out of the ocular results in the IOP to deviate from the normal value of 22 mm of Hg. The Rho GAP pathway playing a crucial role in the modulation of the contractile and relaxation property of the actin smooth muscle, has shown in neg. regulating the protein kinase and subsequently increased IOP. In-vitro and Ex-vitro inhibition of the Rho GTPase protein through inhibitors have resulted in the relaxation of the actin and hence the IOP. The aim of the study is to use the in-silico technique such as, Autodock4, to explore the ligand interaction and its ability to inhibit the activity of RhoGTPase. The mols. AZA1 and Azaindole, with the least binding energies, have proven to be a potent inhibitor of the protein, hence as a lead towards the treatment of the glaucoma by decreasing the IOP to an extent.

Materials Today: Proceedings published new progress about 71203-35-5. 71203-35-5 belongs to pyrazoles-derivatives, auxiliary class GPCR/G Protein,Ras, name is 4-(5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonamide, and the molecular formula is C20H23N3O2S, SDS of cas: 71203-35-5.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Yang, Feng V. published the artcileParallel synthesis of N-biaryl quinolone carboxylic acids as selective M₁ positive allosteric modulators, HPLC of Formula: 763120-58-7, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(2), 531-536, database is CAplus and MEDLINE.

An iterative analog library synthesis approach was employed in the exploration of a quinolone carboxylic acid series of selective M₁ pos. allosteric modulators, and strategies for improving potency and plasma free fraction were identified.

Bioorganic & Medicinal Chemistry Letters published new progress about 763120-58-7. 763120-58-7 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic acid and ester, name is 1H-Pyrazole-4-boronic acid, and the molecular formula is C7H8N2, HPLC of Formula: 763120-58-7.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Noel, Romain published the artcileSynthesis and SAR of 4-(pyrazol-3-yl)-pyridines as novel c-jun N-terminal kinase inhibitors, Related Products of pyrazoles-derivatives, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(9), 2732-2735, database is CAplus and MEDLINE.

The design and synthesis of a novel series of c-jun N-terminal kinase (JNK) inhibitors is described. The development of the 4-(pyrazol-3-yl)-pyridine series, e.g. I, was discovered from an earlier pyrimidine series of JNK inhibitors. Through the optimization of the (pyrazolyl)pyridine scaffold, several potent compounds with good in vivo profiles were discovered.

Bioorganic & Medicinal Chemistry Letters published new progress about 724710-02-5. 724710-02-5 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1H-Pyrazol-5-yl)boronic acid, and the molecular formula is C3H5BN2O2, Related Products of pyrazoles-derivatives.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics

Wang, An published the artcileStudy on ring-opening polymerization of ε-caprolactone catalyzed by Zn(II) Schiff-base complex, Application In Synthesis of 4551-69-3, the publication is Shandong Huagong (2018), 47(20), 5-7, database is CAplus.

Ring-opening polymerization of ε-caprolactone catalyzed by Zn(II) Schiff-base complex [LZn] was studied. Using the selected [LZn] as the catalyst and 4-dimethylaminopyridine as the co-catalyst from the polymerization temperature of 80°C and the reaction time of 6 h in the solvent of toluene, the ring-opening polymerization of ε-caprolactone was carried out under nitrogen atm., where the Mn of the PCL was 24.653×10³ g·mol^-1 and the PDI was 1.21. The results showed that the effective ring-opening polymerization of ε-caprolactone was realized with the presence of catalyst [LZn].

Shandong Huagong published new progress about 4551-69-3. 4551-69-3 belongs to pyrazoles-derivatives, auxiliary class Benzenes, name is 4-Benzoyl-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and the molecular formula is C9H17NO, Application In Synthesis of 4551-69-3.

Referemce:
https://en.wikipedia.org/wiki/Pyrazole,
Pyrazoles – an overview | ScienceDirect Topics