Month: February 2023

Discovery and SAR Evolution of Pyrazole Azabicyclo[3.2.1]octane Sulfonamides as a Novel Class of Non-Covalent N-Acylethanolamine-Hydrolyzing Acid Amidase (NAAA) Inhibitors for Oral Administration was written by Di Fruscia, Paolo;Carbone, Anna;Bottegoni, Giovanni;Berti, Francesco;Giacomina, Francesca;Ponzano, Stefano;Pagliuca, Chiara;Fiasella, Annalisa;Pizzirani, Daniela;Ortega, Jose Antonio;Nuzzi, Andrea;Tarozzo, Glauco;Mengatto, Luisa;Giampa, Roberta;Penna, Ilaria;Russo, Debora;Romeo, Elisa;Summa, Maria;Bertorelli, Rosalia;Armirotti, Andrea;Bertozzi, Sine Mandrup;Reggiani, Angelo;Bandiera, Tiziano;Bertozzi, Fabio. And the article was included in Journal of Medicinal Chemistry in 2021.Application In Synthesis of tert-Butyl (4-hydroxycyclohexyl)carbamate This article mentions the following:

Inhibition of intracellular N-acylethanolamine-hydrolyzing acid amidase (NAAA) activity is a promising approach to manage the inflammatory response under disabling conditions. In fact, NAAA inhibition preserves endogenous palmitoylethanolamide (PEA) from degradation, thus increasing and prolonging its anti-inflammatory and analgesic efficacy at the inflamed site. In the present work, we report the identification of a potent, systemically available, novel class of NAAA inhibitors, featuring a pyrazole azabicyclo[3.2.1]octane structural core. After an initial screening campaign, a careful structure-activity relationship study led to the discovery of endo-ethoxymethyl-pyrazinyloxy-8-azabicyclo[3.2.1]octane-pyrazole sulfonamide 50 (ARN19689), which was found to inhibit human NAAA in the low nanomolar range (IC₅₀ = 0.042μM) with a non-covalent mechanism of action. In light of its favorable biochem., in vitro and in vivo drug-like profile, sulfonamide 50 could be regarded as a promising pharmacol. tool to be further investigated in the field of inflammatory conditions. In the experiment, the researchers used many compounds, for example, tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2Application In Synthesis of tert-Butyl (4-hydroxycyclohexyl)carbamate).

tert-Butyl (4-hydroxycyclohexyl)carbamate (cas: 224309-64-2) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Application In Synthesis of tert-Butyl (4-hydroxycyclohexyl)carbamate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reactivity-based one-pot synthesis of the tumor-associated antigen N3 minor octasaccharide for the development of a photo-cleavable DIOS-MS sugar array was written by Lee, Jinq-Chyi;Wu, Chung-Yi;Apon, Junefredo V.;Siuzdak, Gary;Wong, Chi-Huey. And the article was included in Angewandte Chemie, International Edition in 2006.Quality Control of 3-(Hydroxymethyl)-4-nitrophenol This article mentions the following:

Readily available thioglycosides with defined relative reactivity values were used as building blocks in a one-pot strategy to synthesize the tumor-associated oligosaccharide antigen N3 minor. The target mol. was attached covalently to a porous silicon surface through a photo-cleavable linker for direct characterization in a mass spectrometer equipped with a laser source. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Quality Control of 3-(Hydroxymethyl)-4-nitrophenol).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Quality Control of 3-(Hydroxymethyl)-4-nitrophenol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Stereodynamic Chemosensor with Selective Circular Dichroism and Fluorescence Readout for in Situ Determination of Absolute Configuration, Enantiomeric Excess, and Concentration of Chiral Compounds was written by Bentley, Keith W.;Wolf, Christian. And the article was included in Journal of the American Chemical Society in 2013.Formula: C4H11NO This article mentions the following:

A stereodynamic chemosensor, 1-(4′-pyridyl)-8-(3′-formyl-4′-hydroxyphenyl)naphthalene N-oxide, having a parallel arrangement of a substrate-binding salicylaldehyde unit and an adjacent pyridyl N-oxide fluorophore undergoes rapid condensation with chiral amino alcs. and subsequent asym. transformation of the 1st kind toward a single rotamer. Crystallog. anal. shows that the concomitant central-to-axial chirality imprinting is controlled by minimization of steric repulsion and by intramol. hydrogen bonding between the bound amino alc. and the proximate N-oxide group. The substrate binding event results in strong CD effects and characteristic fluorescence changes which can be used for instantaneous in situ determination of the absolute configuration, enantiomeric composition and total concentration of a variety of chiral amino alcs. This chemosensing approach avoids time-consuming workup and purification steps, and it is applicable to minute sample amounts which reduces the use of solvents and limits waste production In the experiment, the researchers used many compounds, for example, (R)-2-Aminobutan-1-ol (cas: 5856-63-3Formula: C4H11NO).

(R)-2-Aminobutan-1-ol (cas: 5856-63-3) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Formula: C4H11NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Design of New Photoactivatable Amino Acids: Stereoselective Synthesis of N-Protected Phenylalanine Derivatives as Precursors of p-Diazocyclohexadienone-Containing Peptides was written by Dugave, C.. And the article was included in Journal of Organic Chemistry in 1995.Electric Literature of C7H7NO4 This article mentions the following:

4-Diazocyclohexa-2,5-dienone-based amino acids I were designed for building up photoactivatable peptides. Their stable precursors II [R = Me₃CO₂C (Boc), 9-fluorenylmethoxycarbonyl (Fmoc)] were synthesized by stereoselective alkylation of the corresponding benzyloxynitrobenzyl iodides by a chiral glycine equivalent Alkylation was carried out using either butyllithium in dry organic solvents or a phase transfer procedure. Alkylation, hydrolysis of the adduct, and protection as Boc and Fmoc derivatives were achieved in 57-73% overall yields and led to 97-99% optically pure material. II were inserted in model dipeptides by a homogeneous solution procedure and by solid-phase peptide synthesis. Deprotection and diazotization of the resulting p-hydroxyanilines gave the corresponding photoactivatable 4-diazocyclohexa-2,5-dienone-containing peptides in quant. yields. Such photoprobes are stable for several hours in the dark but are rapidly photolyzed at 350 nm or at 295 nm by a tryptophan-mediated energy transfer activation process. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Electric Literature of C7H7NO4).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Electric Literature of C7H7NO4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Biogenesis of a bacterial metabolosome for propanediol utilization was written by Yang, Mengru;Wenner, Nicolas;Dykes, Gregory F.;Li, Yan;Zhu, Xiaojun;Sun, Yaqi;Huang, Fang;Hinton, Jay C. D.;Liu, Lu-Ning. And the article was included in Nature Communications in 2022.Related Products of 57-55-6 This article mentions the following:

Bacterial metabolosomes are a family of protein organelles in bacteria. Elucidating how thousands of proteins self-assemble to form functional metabolosomes is essential for understanding their significance in cellular metabolism and pathogenesis. Here we investigate the de novo biogenesis of propanediol-utilization (Pdu) metabolosomes and characterize the roles of the key constituents in generation and intracellular positioning of functional metabolosomes. Our results demonstrate that the Pdu metabolosome undertakes both “Shell first” and “Cargo first” assembly pathways, unlike the β-carboxysome structural analog which only involves the “Cargo first” strategy. Shell and cargo assemblies occur independently at the cell poles. The internal cargo core is formed through the ordered assembly of multiple enzyme complexes, and exhibits liquid-like properties within the metabolosome architecture. Our findings provide mechanistic insight into the mol. principles driving bacterial metabolosome assembly and expand our understanding of liquid-like organelle biogenesis. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Related Products of 57-55-6).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Related Products of 57-55-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Highly regioselective tandem hydroformylation of substituted styrene using Iminophosphine rhodium complex immobilized on carbon was written by Singh, Amravati S.;Jindani, Sana;Ganguly, Bishwajit;Biradar, Ankush V.. And the article was included in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) in 2022.Recommanded Product: 1,2-Propanediol This article mentions the following:

Reported the sustainable route for the synthesis of ionic carbon from bio-derived sugarcane-waste (Bagasse) and further anchoring with iminophosphine rhodium complex (Rh@BCNP) and utilized for tandem hydroformylation reaction. The SEM anal. confirmed the formation of spherical shape morphol. of carbon with sizes ranging from 30-150 nm. The successful functionalization of the iminophosphine rhodium complex on the carbon surface were determined by XPS, TEM, FE-SEM, ³¹P NMR, ¹³C CP-MAS-NMR and FTIR anal. Furthermore, ICP-OES anal. confirmed the presence of 0.307 mmoles/g of Rh and 0.484 mmoles/g of P on the carbon surface. Rh@BCNP catalyst was the best combination of triphenylphosphine ligand, imine and rhodium metal, resulting in hybrid material with some acidic properties of carbon that favor the selectivity towards linear products. Rh@BCNP showed remarkable catalytic performance under moderate reaction conditions (80°C, 40 bar (CO + H₂)) in 5 h. This sharp divergence from other methods leading to linear amines and acetals results in a novel atom economic approach to synthesize pharmaceuticals and industrial products. The Rh@BCNP catalyst gave recyclability up to five cycles. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Recommanded Product: 1,2-Propanediol).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Recommanded Product: 1,2-Propanediol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of some new sulfonylureas was written by Loev, Bernard;Snader, Kenneth M.;Walz, Donald T.. And the article was included in Journal of Medicinal Chemistry in 1963.SDS of cas: 2968-93-6 This article mentions the following:

The sulfonamides were prepared by treating the sulfonyl chlorides with anhydrous NH₃. The styrene sulfonamides were prepared according to Bordwell, et al. (CA 40, 1466⁵, 7176¹). The sulfonylureas were prepared by treating the sulfonamide with BuNCO in aqueous Me₂CO and the amino-substituted sulfonylurea was prepared by treating the isocyanate with the aminosulfonamide and by reduction of the nitrosulfonylurea. The following I were prepared (X, A, and m.p. given): 4-Cl, CH₂, 180-1°; 4-NO₂, CH₂ (II), 193.5-4.5°; H, CH₂CH₂, 159-61°; 4-NO₂, CH₂CH₂, 153-5°; 2-NO₂, CH₂CH₂, 154-6°; 4-NH₂, CH₂CH₂, 129-31°; 4-AcNH, CH₂CH₂, 206° (decomposition); 4-CN, CH₂CH₂ (III), 143-8° (decomposition); 4-CONH₂, CH₂CH₂, 197-9° (decomposition); 4-CO₂Et, CH₂CH₂, 127-30° (decomposition). 4-CO₂H, CH₂CH₂, 172-4° (decomposition); 4-CF₃, CH₂CH₂, 158-9°; H, CH:CH, 128-30°; 4-NO₂, CH:CH, 190-90.5°. The following IV were also prepared (X, A, and m.p. given): 4-NO₂, CH₂CH₂, 118-21°; 2-NO₂, CH₂CH₂, 125-7°; 4-CN, CH₂CH₂, 105-8°; 4-AcNH, CH₂CH₂, 159-60°; 4-CONH₂, CH₂CH₂, 197-9°; 4-CO₂Et, CH₂CH₂, 103-10°; 4-CO₂H, CH₂CH₂, 232-5° (decomposition); 4-CF₃, CH₂CH₂, 110-13°; 4-NO₂, CH:CH, 188-90°. II and III were found to have hypoglycemic activity equal to chlorpropamide when tested by the modified method of Hoffman (CA 31, 8583⁴). In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6SDS of cas: 2968-93-6).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.SDS of cas: 2968-93-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Redox-Neutral Borylation of Aryl Sulfonium Salts via C-S Activation Enabled by Light was written by Huang, Chen;Feng, Jie;Ma, Rui;Fang, Shuaishuai;Lu, Tao;Tang, Weifang;Du, Ding;Gao, Jian. And the article was included in Organic Letters in 2019.Synthetic Route of C12H16BBrO2 This article mentions the following:

Reported here is a novel photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the B source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied by mild conditions, operational simplicity, and easy scalability. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Synthetic Route of C12H16BBrO2).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Synthetic Route of C12H16BBrO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Orange peel fermentation using Lactiplantibacillus plantarum: microbiological analysis and physico-chemical characterisation was written by Deba-Rementeria, Shuyana;Estrada, Olaia;Issa-Issa, Hanan;Vazquez-Araujo, Laura. And the article was included in International Journal of Food Science and Technology in 2022.Related Products of 149-32-6 This article mentions the following:

Summary : To find an innovative use for orange peels discarded in the orange juice-making process, a fermentative process was assessed using a Lactiplantibacillus plantarum strain. Blanched or rinsed peels were submerged in a 5% NaCl-3% inoculated sucrose brine for 10 days. Total soluble solids, pH, sugars and total aerobic and anaerobic counts were determined in the brines to characterize the process. The final products were characterised by instrumental texture, color and volatile composition The blanching pretreatment had a significant effect on the whole process and the final product characteristics. Anaerobic bacteria total counts were significantly higher in the blanched samples during the whole fermentation, and pH decreased significantly slower in these samples than in the rinsed ones. Rinsed samples were characterised by higher aerobic total counts, higher sucrose consumption and higher glucose, fructose and polyalcs. production The texture was softer in the pretreated samples, probably due to the blanching process rather than the fermentation The volatile composition was quite similar between samples, although it was different from one of the raw orange peels due to a significant decrease in various volatile compounds In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Related Products of 149-32-6).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Related Products of 149-32-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Tandem absorbance and fluorescence detection following liquid chromatography for the profiling of multiclass phenolic compounds in different winemaking products was written by Ferreyra, Susana;Bottini, Ruben;Fontana, Ariel. And the article was included in Food Chemistry in 2021.HPLC of Formula: 10083-24-6 This article mentions the following:

A liquid chromatog. method coupling diode-array and fluorescence detectors (DAD and FLD, resp.) has been developed for the simultaneous quantification of 32 phenolic compounds (PCs) in winemaking products. With the combination of both detectors it was possible to determine phenolic acids, flavanols, flavonols, stilbenes and other PCs in the matrixes under study. An excitation wavelength of 290 nm was selected and three different emission wavelengths (315, 360 and 400 nm) were recorded. The method provided detection and quantification limits (LODs and LOQs) within the ranges of 0.01-1.46 mg/L and 0.03-4.9 mg/L, resp. The LODs and LOQs using FLD for flavanols, stilbenes and Ph ethanol analogs were improved between 65 and 1000% as compared with DAD. The combination of DAD with FLD increased both, sensitivity and the ability to reduce interfering signals. The developed method was applied for the characterization of PCs of wines, bunch stems and grape canes. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6HPLC of Formula: 10083-24-6).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.HPLC of Formula: 10083-24-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts