Day: November 28, 2022

Naus, Petr published the artcileCytostatic and antiviral 6-arylpurine ribonucleosides IX. synthesis and evaluation of 6-substituted 3-deazapurine ribonucleosides, Application In Synthesis of 724710-02-5, the publication is Collection of Czechoslovak Chemical Communications (2008), 73(5), 665-678, database is CAplus.

A series of 3-deazapurine ribonucleosides bearing diverse C-substituents (alkyl, aryl and heteroaryl) in the position 6 were prepared by Pd-catalyzed cross-coupling reactions of either free 6-chloro-3-deazapurine ribonucleoside or its acetyl protected congener followed by deprotection. An improved synthesis of the starting 4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridine was developed by the application of Vorbruggen glycosylation of silylated nucleobase with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. None of title compounds showed any considerable cytostatic or antiviral activity.

Collection of Czechoslovak Chemical Communications 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, Application In Synthesis of 724710-02-5.

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

Ivachtchenko, Alexandre V. published the artcileSynthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids, SDS of cas: 847818-66-0, the publication is Journal of Heterocyclic Chemistry (2004), 41(6), 931-939, database is CAplus.

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.

Journal of Heterocyclic Chemistry published new progress about 847818-66-0. 847818-66-0 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Boronic Acids,Boronic Acids,Boronic acid and ester, name is (1-Isopentyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C8H15BN2O2, SDS of cas: 847818-66-0.

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

Ivachtchenko, Alexandre V. published the artcileSynthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids, Quality Control of 847818-64-8, the publication is Journal of Heterocyclic Chemistry (2004), 41(6), 931-939, database is CAplus.

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.

Journal of Heterocyclic Chemistry published new progress about 847818-64-8. 847818-64-8 belongs to pyrazoles-derivatives, auxiliary class Pyrazole,Boronic acid and ester,Pyrazole,Boronic Acids,Boronic acid and ester, name is (1-Isobutyl-1H-pyrazol-5-yl)boronic acid, and the molecular formula is C7H13BN2O2, Quality Control of 847818-64-8.

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

Ul′yanovskii, Nikolay V. published the artcileRapid quantification and screening of nitrogen-containing rocket fuel transformation products by vortex assisted liquid-liquid microextraction and gas chromatography – high-resolution Orbitrap mass spectrometry, Formula: C4H6N2, the publication is Microchemical Journal (2021), 106821, database is CAplus.

Existing and newly developed technologies for clean-up of wastewaters and soils contaminated with rocket fuel unsym. dimethylhydrazine (UDMH) are based on the oxidative treatment, as well as gasification in supercritical water. Being easily transformed by a radical mechanism, UDMH is capable of producing an extremely wide range of potentially hazardous nitrogen-containing products. Their identification and simultaneous quantification at low concentrations in water samples by gas chromatog. is a challenging task requiring a matrix change. We proposed a combination of dispersive vortex-assisted liquid-liquid microextraction (VALLME) of analytes followed by gas chromatog. – Orbitrap mass spectrometry allowing simultaneous target anal. and non-targeted screening. Dichloromethane and chloroform provided rapid (10 min) and effective extraction of most of UDMH transformation products. The maximum recoveries were achieved by alkalizing and saturating the aqueous samples with ammonium sulfate. The use of pyridine-d5 as an internal standard allowed developing an approach to the simultaneous determination of 24 compounds of various classes with detection limits for the most analytes in the range 0.02-1.1 μg L^-1 and accuracy of 81-117% with low-cost, simple, and rapid sample preparation procedure. Extraction with a 100 μL of chloroform allowed further increasing sensitivity up to one order of magnitude and attaining LOD values for 20 compounds in the range of 0.002-0.1 μg L^-1 comparable with that obtained by vacuum-assisted headspace solid-phase microextraction The developed method was validated and tested for the analyses of real samples – degraded aqueous solution of rocket fuel, products of UDMH treatment in supercritical water and aqueous extract of soil from the place of carrier rocket accidental crash. Twenty-nine compounds that were not previously described as UDMH transformation products were tentatively identified.

Microchemical Journal 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 C10H14O, Formula: C4H6N2.

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

Kasparkova, Jana published the artcileNovel cis-Pt(II) complexes with alkylpyrazole ligands: synthesis, characterization, and unusual mode of anticancer action, Quality Control of 930-36-9, the publication is Bioinorganic Chemistry and Applications (2022), 1717200, database is CAplus and MEDLINE.

One concept of improving anticancer effects of conventional platinum-based antitumor drugs consists of conjugating these compounds with other biol. (antitumor) active agents, acting by a different mechanism. Here, we present synthesis, physicochem. characterization, biol. effects, and mechanisms of action of four new analogs of conventional cisplatin, namely, cis-Pt(II) complexes containing either Me or Et pyrazole N-donor ligands and chlorido or iodido ligands. It is noteworthy that while chlorido complexes display activity in a variety of cancer cell lines comparable to cisplatin, iodido complexes are considerably more potent due to their enhanced hydrophobicity and consequently enhanced cellular accumulation. Moreover, all of the studied Pt(II) alkylpyrazole complexes display a higher selectivity for tumor cells and effectively overcome the acquired resistance to cisplatin. Further results focused on the mechanism of action of the studied complexes and showed that in contrast to cisplatin and several platinum-based antitumor drugs, DNA damage by the investigated Pt(II)-alkylpyrazole complexes does not play a major role in their mechanism of action. Our findings demonstrate that inhibition of the tubulin kinesin Eg5, which is essential for forming a functional mitotic spindle, plays an important role in their mechanism of antiproliferative action.

Bioinorganic Chemistry and Applications 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, Quality Control of 930-36-9.

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

Thottacherry, Joseph Jose published the artcileMechanochemical feedback control of dynamin independent endocytosis modulates membrane tension in adherent cells, HPLC of Formula: 71203-35-5, the publication is Nature Communications (2018), 9(1), 1-14, database is CAplus and MEDLINE.

Plasma membrane tension regulates many key cellular processes. It is modulated by, and can modulate, membrane trafficking. However, the cellular pathway(s) involved in this interplay is poorly understood. Here we find that, among a number of endocytic processes operating simultaneously at the cell surface, a dynamin independent pathway, the CLIC/GEEC (CG) pathway, is rapidly and specifically upregulated upon a sudden reduction of tension. Moreover, inhibition (activation) of the CG pathway results in lower (higher) membrane tension. However, alteration in membrane tension does not directly modulate CG endocytosis. This requires vinculin, a mechano-transducer recruited to focal adhesion in adherent cells. Vinculin acts by controlling the levels of a key regulator of the CG pathway, GBF1, at the plasma membrane. Thus, the CG pathway directly regulates membrane tension and is in turn controlled via a mechano-chem. feedback inhibition, potentially leading to homeostatic regulation of membrane tension in adherent cells.

Nature Communications 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 C20H19NO4, HPLC of Formula: 71203-35-5.

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

Jagtap, Ajit Dhananjay published the artcile4-Substituted 2-amino-3,4-dihydroquinazolines with a 3-hairpin turn side chain as novel inhibitors of BACE-1, Recommanded Product: 1-Methylpyrazole, the publication is Bioorganic Chemistry (2020), 103135, database is CAplus and MEDLINE.

Herein, the authors report the identification, design, and synthesis of a series of 4-substituted 2-amino-3,4-dihydroquinazolines I [R¹ = Me, CH:CH₂, Bn, etc., R² = Me, cyclopropyl, (1-methyl-1H-pyrazol-4-yl)methyl] with hairpin turn side chains as novel inhibitors of BACE-1. The dihydroquinazoline derivatives were rationally designed by modifying the amide group and relocating the α-hydrophobic substituent on the hairpin turn side chain of lead compound II to the C4-position on the 3,4-dihydroquinazoline scaffold to facilitate interactions with the S₁, S₂ and S₁‘ subsites of BACE-1. Among these derivatives, two compounds exhibited potent BACE-1 inhibitory activity: 4-methyl-substituted derivative I [R¹ = Me, R² = (1-methyl-1H-pyrazol-4-yl)methyl] (BACE-1 CFA IC₅₀ = 0.38μM; BACE-1 WCA IC₅₀ = 0.14μM) and 4-cyclohexylmethyl-substituted derivative I [R¹ = cyclohexylmethyl, R² = (1-methyl-1H-pyrazol-4-yl)methyl] (BACE-1 CFA IC₅₀ = 0.49μM; BACE-1 WCA IC₅₀ = 0.14μM). The results suggest that the structural modifications maintain the hairpin turn topol. similar to that of compound II and provide an addnl. interaction with the S₂ subsite.

Bioorganic 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, Recommanded Product: 1-Methylpyrazole.

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

Petzold, Daniel published the artcilePhotocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone, Category: pyrazoles-derivatives, the publication is Advanced Synthesis & Catalysis (2018), 360(4), 626-630, database is CAplus.

The estimated excited oxidation potential of sodium anthraquinone-2-sulfonate (SAS) increases from 1.8 V to ∼2.3 V vs. SCE by protonation with Bronsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio-selective oxidative bromination of electron rich (hetero)arenes and drugs in good yield. The mild reaction conditions are compatible with many functional groups, such as double and triple bonds, ketones, amides and amines, hydroxyl groups, carboxylic acids and carbamates. Mechanistic studies indicate the photooxidation of the arene followed by nucleophilic bromide addition as the likely pathway.

Advanced Synthesis & 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

Shinozuka, Tsuyoshi published the artcileDiscovery of DS-1971a, a Potent, Selective Na_V1.7 Inhibitor, Category: pyrazoles-derivatives, the publication is Journal of Medicinal Chemistry (2020), 63(18), 10204-10220, database is CAplus and MEDLINE.

A highly potent, selective Na_V1.7 inhibitor, DS-1971a(I), has been discovered. Exploration of the left-hand Ph ring of sulfonamide derivatives (I and II) led to the discovery of novel series of cycloalkane derivatives with high Na_V1.7 inhibitory potency in vitro. As the right-hand heteroaromatic ring affected the mechanism-based inhibition liability of CYP3A4, replacement of this moiety resulted in the generation of 4-pyrimidyl derivatives Addnl., GSH adducts formation, which can cause idiosyncratic drug toxicity, was successfully avoided by this modification. An addnl. optimization led to the discovery of DS-1971a. In preclin. studies, DS-1971a demonstrated highly potent selective in vitro profile with robust efficacy in vivo. DS-1971a exhibited a favorable toxicol. profile, which enabled multiple-dose studies of up to 600 mg bid or 400 mg tid (1200 mg/day) administered for 14 days to healthy human males. DS-1971a is expected to exert potent efficacy in patients with peripheral neuropathic pain, with a favorable safety profile.

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 C22H23ClN4, Category: pyrazoles-derivatives.

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

Wietelmann, Ulrich published the artcileContinuous Processing of Concentrated Organolithiums in Flow Using Static and Dynamic Spinning Disc Reactor Technologies, Name: 1-Methylpyrazole, the publication is Organic Process Research & Development (2022), 26(5), 1422-1431, database is CAplus.

Organometallic reactions involving highly reactive organolithium reagents are widely used in organic synthesis. However, the use of organometallics in batch mode on a pilot and industrial scale is challenging for safety reasons and frequently requires expensive cryogenic process conditions. A change to continuous processing in flow mode can provide major advantages for process safety and economics. In this study, we compare static and dynamic flow reactor technologies for two important organolithium (butyllithium and hexyllithium)-enabled transformations: deprotonations and bromine/lithium exchange reactions. Using higher concentrated (≥3 M) butyllithium (BuLi) solutions, i.e., reaction mixtures with reduced hydrocarbon content, decreases the risk of reactor fouling and allows for increased space/time yields. In the flow mode, the observed reactions could be carried out under more convenient conditions, i.e., at higher temperatures compared to the batch mode, and the deprotonation reaction even at ambient temperature instead of -78°C. The formation of precipitates with the risk of clogging can be further reduced by changing from static flow to dynamic spinning disk reactor technol. The SpinPro reactor system from Flowid has been identified to ensure robust performance, as it tolerates salt precipitations and can provide excellent mass transfer conditions. Flow process technol. using concentrated organolithium products can provide unique benefits for the manufacturing of pharmaceutical intermediates, agrochem. products, and specialty chems.

Organic Process Research & Development 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 C20H23N3O2S, Name: 1-Methylpyrazole.

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