Month: November 2022

Pandit, Rameshwar Prasad published the artcileEfficient one-pot synthesis of novel and diverse tetrahydroquinolines bearing pyranopyrazoles using organocatalyzed domino Knoevenagel/hetero Diels-Alder reactions, Formula: C10H9ClN2O, the publication is Molecular Diversity (2014), 18(1), 39-50, database is CAplus and MEDLINE.

A new synthetic route to biol. interesting diverse tetrahydroquinoline derivatives bearing pyranopyrazole groups was developed and the synthesis of the target compounds was achieved by a reaction of pyrazolones and N,N-dialkylated aminobenzaldehyde derivatives in the presence of 1,2-Ethanediamine acetate (1:2) (EDDA, ethylenediammonium diacetate). The key strategy underlying the methodol. used was the domino Knoevenagel/hetero Diels-Alder reaction. This synthetic method provides a variety of novel tetrahydroquinolines in good yields. The title compounds thus formed included a heterocyclic compound (I) and related substances. The synthesis of the target compounds was achieved by a reaction of 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one derivatives with 2-[methyl(3-methyl-2-buten-1-yl)amino]benzaldehyde (prenylamine derivative), 2-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]methylamino]benzaldehyde (trans-geranylamine derivative), 2-[methyl[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]amino]benzaldehyde (trans,trans-farnesylamine derivative).

Molecular Diversity published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Formula: C10H9ClN2O.

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

Cho, Sung Yun published the artcileDesign and synthesis of novel 3-(benzo[d]oxazol-2-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine derivatives as selective G-protein-coupled receptor kinase-2 and -5 inhibitors, HPLC of Formula: 1190875-39-8, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(24), 6711-6716, database is CAplus and MEDLINE.

G-protein-coupled receptor kinase (GRK)-2 and -5 are emerging therapeutic targets for the treatment of cardiovascular disease. In the efforts to discover novel small mols. to inhibit GRK-2 and -5, a class of compound based on 3-(benzo[d]oxazol-2-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine was identified as a novel hit by high throughput screening campaign. Structural modification of parent benzoxazole scaffolds by introducing substituents on Ph displayed potent inhibitory activities toward GRK-2 and -5.

Bioorganic & Medicinal Chemistry Letters published new progress about 1190875-39-8. 1190875-39-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Piperidine,Boronic acid and ester,Amide,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-(1-(tert-Butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)boronic acid, and the molecular formula is C13H22BN3O4, HPLC of Formula: 1190875-39-8.

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

Cox, Paul A. published the artcileProtodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH-Rate Profiles, Autocatalysis, and Disproportionation, Quality Control of 763120-58-7, the publication is Journal of the American Chemical Society (2016), 138(29), 9145-9157, database is CAplus and MEDLINE.

PH-rate profiles for aqueous-organic protodeboronation of 18 boronic acids, many widely viewed as unstable, have been studied by NMR and DFT. Rates were pH-dependent, and varied substantially between the boronic acids, with rate maxima that varied over 6 orders of magnitude. A mechanistic model containing five general pathways (k₁-k₅) has been developed, and together with input of [B]_tot, K_W, K_a, and K_aH, the protodeboronation kinetics can be correlated as a function of pH (1-13) for all 18 species. Cyclopropyl and vinyl boronic acids undergo very slow protodeboronation, as do 3- and 4-pyridyl boronic acids (t_0.5 > 1 wk, pH 12, 70 °C). In contrast, 2-pyridyl and 5-thiazolyl boronic acids undergo rapid protodeboronation (t_0.5 ≈ 25-50 s, pH 7, 70 °C), via fragmentation of zwitterionic intermediates. Lewis acid additives (e.g., Cu, Zn salts) can attenuate (2-pyridyl) or accelerate (5-thiazolyl and 5-pyrazolyl) fragmentation. Two addnl. processes compete when the boronic acid and the boronate are present in sufficient proportions (pH = pK_a ± 1.6): (i) self-/autocatalysis and (ii) sequential disproportionations of boronic acid to borinic acid and borane.

Journal of the American Chemical Society 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 C3H5BN2O2, Quality Control of 763120-58-7.

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

Cox, Paul A. published the artcileProtodeboronation of Heteroaromatic, Vinyl, and Cyclopropyl Boronic Acids: pH-Rate Profiles, Autocatalysis, and Disproportionation, HPLC of Formula: 724710-02-5, the publication is Journal of the American Chemical Society (2016), 138(29), 9145-9157, database is CAplus and MEDLINE.

PH-rate profiles for aqueous-organic protodeboronation of 18 boronic acids, many widely viewed as unstable, have been studied by NMR and DFT. Rates were pH-dependent, and varied substantially between the boronic acids, with rate maxima that varied over 6 orders of magnitude. A mechanistic model containing five general pathways (k₁-k₅) has been developed, and together with input of [B]_tot, K_W, K_a, and K_aH, the protodeboronation kinetics can be correlated as a function of pH (1-13) for all 18 species. Cyclopropyl and vinyl boronic acids undergo very slow protodeboronation, as do 3- and 4-pyridyl boronic acids (t_0.5 > 1 wk, pH 12, 70 °C). In contrast, 2-pyridyl and 5-thiazolyl boronic acids undergo rapid protodeboronation (t_0.5 ≈ 25-50 s, pH 7, 70 °C), via fragmentation of zwitterionic intermediates. Lewis acid additives (e.g., Cu, Zn salts) can attenuate (2-pyridyl) or accelerate (5-thiazolyl and 5-pyrazolyl) fragmentation. Two addnl. processes compete when the boronic acid and the boronate are present in sufficient proportions (pH = pK_a ± 1.6): (i) self-/autocatalysis and (ii) sequential disproportionations of boronic acid to borinic acid and borane.

Journal of the American Chemical Society 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, HPLC of Formula: 724710-02-5.

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

Thach, Thi-Dan published the artcileSynthesis of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents, HPLC of Formula: 71203-35-5, the publication is Journal of the Serbian Chemical Society (2020), 85(2), 155-162, database is CAplus.

Two series of sulfonamides were synthesized from 4-hydrazinylbenzenesulfonamide as the key starting material. 1,3,5-triarylpyrazoline sulfonamides I [R = H, F, MeO; Ar = Ph, 4-MeC₆H₄, 2-HOC₆H₄, 4-MeOC₆H₄] were obtained by cyclocondensation of various chalcones in 53-64% yields, while 4-thiazolidinone derivatives II [Ar¹ = Ph, 4-MeC₆H₄, 2-HOC₆H₄, 4-ClC₆H₄, 4-MeOC₆H₄] were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43-62% yields. The synthesized compounds were characterized based on FTIR, ¹H-NMR, ¹³C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a-c and 2e-h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. niger (MIC value at 12.5μg mL^-1) over the reference drug.

Journal of the Serbian Chemical Society 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 C9H8O4, HPLC of Formula: 71203-35-5.

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

Graton, Jerome published the artcileHydrogen-Bond Accepting Properties of New Heteroaromatic Ring Chemical Motifs: A Theoretical Study, Recommanded Product: 1-Methylpyrazole, the publication is Journal of Chemical Information and Modeling (2016), 56(2), 322-334, database is CAplus and MEDLINE.

The prediction of hydrogen-bond (H-bond) acceptor ability is crucial in drug design. This important property is quantified in a large pK_BHX database of consistently measured values. We aim to expand the chem. diversity of the studied H-bond acceptors and to increase the range of H-bond strength considered. Two quantum chem. descriptors are contrasted, called ΔE(H) (the change in the energy of a topol. hydrogen atom upon complexation) and V_min (the local min. in the electrostatic potential on the H-bond accepting site). We performed a systematic anal. of the correlations between pK_BHX and V_min for an initial set of 106 compounds (including O- and N-containing subsets, as well as compounds including sulfur, chlorine, and π-bases). Correlations improve for family dependent subsets, and after outlier treatment, a set of 90 compounds was used to set up a linear equation to predict pK_BHX from V_min. This equation and a previously published equation, to predict pK_BHX from ΔE(H), were used to predict the pK_BHX values for 22 potentially biol. active heteroaromatic ring compounds, among which several structures still remain exptl. unavailable. H-Bond basicity of sp² nitrogen sites were consistently predicted with both descriptors. A worse agreement was found with carbonyl acceptor sites, with the stronger deviations observed for the lactam groups. It was shown that secondary interactions involving the neighboring NH group were influencing the results. Substitution of the NH group with an NMe group resulted in an improved consistency from both V_min and ΔE(H) predictions, the latter being more prominently affected by the Me substitution. Both approaches appear as efficient procedures for the H-bond ability prediction of novel heteroaromatic rings. Nevertheless, the ΔE(H) parameter presents slight chem. structure limitations and requires more detailed H-bond structure investigations.

Journal of Chemical Information and Modeling 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, Recommanded Product: 1-Methylpyrazole.

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

Robke, Lucas published the artcilePhenotypic Identification of a Novel Autophagy Inhibitor Chemotype Targeting Lipid Kinase VPS34, HPLC of Formula: 851435-28-4, the publication is Angewandte Chemie, International Edition (2017), 56(28), 8153-8157, database is CAplus and MEDLINE.

Autophagy is a critical regulator of cellular homeostasis and metabolism Interference with this process is considered a new approach for the treatment of disease, in particular cancer and neurol. disorders. Therefore, novel small-mol. autophagy modulators are in high demand. We describe the discovery of autophinib, a potent autophagy inhibitor with a novel chemotype. Autophinib was identified by means of a phenotypic assay monitoring the formation of autophagy-induced puncta, indicating accumulation of the lipidated cytosolic protein LC3 on the autophagosomal membrane. Target identification and validation revealed that autophinib inhibits autophagy induced by starvation or rapamycin by targeting the lipid kinase VPS34.

Angewandte Chemie, International Edition published new progress about 851435-28-4. 851435-28-4 belongs to pyrazoles-derivatives, auxiliary class Imidazole,Pyrimidine,Chloride,Amine, name is 2-Chloro-6-methyl-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine, and the molecular formula is C9H10ClN5, HPLC of Formula: 851435-28-4.

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

Gao, Yaojun published the artcileSynthesis of Pyrazolo[5,1-d][1,2,3,5]tetrazin-4(3H)-ones, Name: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, the publication is Journal of Combinatorial Chemistry (2010), 12(1), 69-74, database is CAplus and MEDLINE.

A solid-phase synthesis of 5-aminopyrazoles I (R¹ = H, CN, EtO₂C, Ph; R² = H, Me, Ph) has been developed and applied to the preparation of pyrazolo[5,1-d][1,2,3,5]tetrazin-4(3H)-ones II (R³ = n-hexyl, Ph, 4-ClC₆H₄, PhCH₂, PhCH₂CH₂). In this strategy, 5-aminopyrazoles I were converted into pyrazolo[5,1-d][1,2,3,5]tetrazines II in one-pot via diazotization followed cyclocondensation with isocyanates R³NCO.

Journal of Combinatorial Chemistry published new progress about 23286-70-6. 23286-70-6 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Amine,Ester, name is Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate, and the molecular formula is C7H11N3O2, Name: Ethyl 5-amino-3-methyl-1H-pyrazole-4-carboxylate.

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

Woods, Keith W. published the artcileAminopyrimidinone Cdc7 Kinase Inhibitors, Synthetic Route of 763120-58-7, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(5), 1940-1943, database is CAplus and MEDLINE.

We have investigated the SAR of a series of pyrimidinone-containing Cdc7 kinase inhibitors. A wide range of amine substitutions give potent compounds with activities (K_i) less than 1 nM. Kinase selectivity is reasonable and cytotoxicity corresponds to inhibition of MCM2 phosphorylation.

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 C11H10N4, Synthetic Route of 763120-58-7.

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

Parmar, Narsidas J. published the artcileAn efficient domino Knoevenagel/hetero-Diels-Alder route to some novel thiochromenoquinoline-fused polyheterocycles, Computed Properties of 14580-22-4, the publication is Monatshefte fuer Chemie (2014), 145(7), 1179-1189, database is CAplus.

The 2-alkenylthiopyranoquinoline-3-carbaldehyde derived from 2-mercaptoquinoline-3-carbaldehyde and citral underwent smooth domino Knoevenagel/hetero-Diels-Alder reaction with heterocyclic mono- or diketones in tetrabutylammonium hydrogensulfate under solvent-free conditions and afforded a new class of thiochromenoquinoline-fused heterocycles in good yields. The reaction is highly diastereoselective and can be applied to analogs of carbocyclic diketones as well. The stereochem. of the products was confirmed by single-crystal X-ray diffraction and 2D NMR NOESY data.

Monatshefte fuer Chemie published new progress about 14580-22-4. 14580-22-4 belongs to pyrazoles-derivatives, auxiliary class Organic Pigment, name is 1-(2-Chlorophenyl)-3-methyl-5-pyrazolone, and the molecular formula is C10H9ClN2O, Computed Properties of 14580-22-4.

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