Tag: 200-300

Tertiary amines as highly efficient catalysts in the ring-opening reactions of epoxides with amines or thiols in H₂O: expeditious approach to β-amino alcohols and β-aminothioethers was written by Wu, Jie;Xia, Hong-Guang. And the article was included in Green Chemistry in 2005.Category: alcohols-buliding-blocks This article mentions the following:

Ring-opening of epoxides with various amines or thiols catalyzed by DABCO (1,4-diazabicyclic[2,2,2]octane) or Et₃N (1 mol%) in water afforded the corresponding products in good to excellent yields under mild reaction conditions. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Category: alcohols-buliding-blocks).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) 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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Regioselective ring opening of epoxides with amines using monodispersed silica nanoparticles in water was written by Sreedhar, B.;Radhika, P.;Neelima, B.;Hebalkar, Neha. And the article was included in Journal of Molecular Catalysis A: Chemical in 2007.Application of 40571-86-6 This article mentions the following:

Monodispersed silica nanoparticles were synthesized and used as catalyst for the regioselective synthesis of β-amino alcs. in water via nucleophilic ring opening of epoxides with amines under ambient conditions in shorter reaction times. The use of water as green solvent allows easy recycling of the catalyst. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Application of 40571-86-6).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) 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. 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 of 40571-86-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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

Passion fruit seed extract protects beta-amyloid-induced neuronal cell death in a differentiated human neuroblastoma SH-SY5Y cell model was written by Sato, Akira;Tagai, Nozomi;Ogino, Yoko;Uozumi, Haruka;Kawakami, Shinpei;Yamamoto, Takayuki;Tanuma, Sei-ichi;Maruki-Uchida, Hiroko;Mori, Sadao;Morita, Minoru. And the article was included in Food Science & Nutrition (Hoboken, NJ, United States) in 2022.Quality Control of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol This article mentions the following:

Alzheimers disease (AD) is a progressive neurodegenerative disease with accompanying perceptive disorder. We previously reported that decreasing levels of brain-derived neurotrophic factor (BDNF) promoted beta-amyloid (Aβ)-induced neuronal cell death in neuron-like differentiated SH-SY5Y (ndSH-SY5Y) human neuroblastoma cells in an AD mimic cell model. We investigated the neuroprotective effects of passion fruit seed extract (PFSE) and one of the main stilbene compounds, piceatannol, in an AD cell model using ndSH-SY5Y cells. Both PFSE and piceatannol were found to protect Aβ-induced neurite fragmentation in the cell model (protection efficacy; 34in PFSE and 36in piceatannol). In addition, both PFSE and piceatannol suppress Aβ-induced neuronal cell death in the cell model (inhibitory effect; 27in PFSE and 32in piceatannol). Our study is the first to report that piceatannol-rich PFSE can repress Aβ-induced neuronal cell death by protecting against neurite fragmentation in the AD human cell model. These findings suggest that piceatannol-rich PFSE can be considered a potentially neuroprotective functional food for both prevention and treatment of AD. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6Quality Control of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Anthranilamide (aam)-substituted diboron: palladium-catalyzed selective B(aam) transfer was written by Kamio, Shintaro;Kageyuki, Ikuo;Osaka, Itaru;Hatano, Sayaka;Abe, Manabu;Yoshida, Hiroto. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Reference of 68716-49-4 This article mentions the following:

An unsym. diboron bearing an anthranilamide (aam) substituent was synthesized and was found to be coupled with aryl halides through the palladium-catalyzed Miyaura-Ishiyama-type reaction. The selective transfer of aam-substituted boryl moiety led to exclusive formation of diverse Ar-B(aam). In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Reference of 68716-49-4).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. 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.Reference of 68716-49-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of (3RS,3aSR,8aSR)-3-phenyloctahydrocyclohepta[b]pyrrol-4(1H)-one via the aza-Cope-Mannich rearrangement was written by Belov, Dmitry S.;Lukyanenko, Evgeny R.;Kurkin, Alexander V.;Yurovskaya, Marina A.. And the article was included in Tetrahedron in 2011.Safety of Trans-2-(benzylamino)cyclohexanol This article mentions the following:

A convenient and scalable method for the preparation of (3RS,3aSR,8aSR)-phenyloctahydrocyclohepta[b]pyrrol-4(1H)-one based on the aza-Cope-Mannich rearrangement is described. This approach allows us to synthesize the target compound in nine steps in a high overall yield (42%) with complete stereocontrol and up to 100 g scale. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Safety of Trans-2-(benzylamino)cyclohexanol).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) 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. 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.Safety of Trans-2-(benzylamino)cyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp²-sp³ Cross-Coupling was written by Xu, Meng-Yu;Jiang, Wei-Tao;Li, Ying;Xu, Qing-Hao;Zhou, Qiao-Lan;Yang, Shuo;Xiao, Bin. And the article was included in Journal of the American Chemical Society in 2019.Category: alcohols-buliding-blocks This article mentions the following:

Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp³)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp²)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp³)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp³)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analog. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an “S_E2(open) Inv” pathway, which is consistent with Hiyama’s previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Category: alcohols-buliding-blocks).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Structure-based design, synthesis, and biological evaluation of novel piperine-resveratrol hybrids as antiproliferative agents targeting SIRT-2 was written by Tantawy, Ahmed H.;Meng, Xiang-Gao;Marzouk, Adel A.;Fouad, Ali;Abdelazeem, Ahmed H.;Youssif, Bahaa G. M.;Jiang, Hong;Wang, Man-Qun. And the article was included in RSC Advances in 2021.Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol This article mentions the following:

A series of novel piperine-resveratrol hybrids 5a-h was designed, synthesized, and structurally elucidated by IR, and ¹H, ¹³C, and ¹⁹F NMR. Antiproliferative activities of 5a-h were evaluated by NCI against sixty cancer cell lines. Compound 5b, possessing resveratrol pharmacophoric phenolic moieties, showed a complete cell death against leukemia HL-60 (TB) and Breast cancer MDA-MB-468 with growth inhibition percentage of -0.49 and -2.83, resp. In addition, 5b recorded significant activity against the other cancer cell lines with growth inhibition percentage between 80 to 95. New 5a-h hybrids were evaluated for their inhibitory activities against Sirt-1 and Sirt-2 as mol. targets for their antiproliferative action. Results showed that compounds 5a-h were more potent inhibitors of Sirt-2 than Sirt-1 at 5 μm and 50 μm. Compound 5b showed the strongest inhibition of Sirt-2 (78 ± 3% and 26 ± 3% inhibition at 50 μM and 5 μM, resp.). Investigation of intermol. interaction via Hirschfeld surface anal. indicates that these close contacts are mainly ascribed to the O-H ···O hydrogen bonding. To get insights into the Sirt-2 inhibitory mechanism, a docking study was performed where 5b was found to fit nicely inside both extended C-pocket and selectivity pocket and could compete with the substrate acyl-Lys. Another possible binding pattern showed that 5b could act by partial occlusion of the NAD+ C-pocket. Collectively, these findings would contribute significantly to better understanding the Sirt-2 inhibitory mechanism in order to develop a new generation of refined and selective Sirt-2 inhibitors. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Application In Synthesis of (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

De-Novo Design of Cereblon (CRBN) Effectors Guided by Natural Hydrolysis Products of Thalidomide Derivatives was written by Heim, Christopher;Pliatsika, Dimanthi;Mousavizadeh, Farnoush;Baer, Kerstin;Hernandez Alvarez, Birte;Giannis, Athanassios;Hartmann, Marcus D.. And the article was included in Journal of Medicinal Chemistry in 2019.Quality Control of tert-Butyl (cis-4-(hydroxymethyl)cyclohexyl)carbamate This article mentions the following:

Targeted protein degradation via cereblon (CRBN), a substrate receptor of an E3 ubiquitin ligase complex, is an increasingly important strategy in various clin. settings, in which the substrate specificity of CRBN is altered via the binding of small-mol. effectors. To date, such effectors are derived from thalidomide and confer a broad substrate spectrum that is far from being fully characterized. Here, we employed a rational and modular approach to design novel and minimalistic CRBN effectors. In this approach, we took advantage of the binding modes of hydrolyzed metabolites of several thalidomide-derived effectors, which we elucidated via crystallog. These yielded key insights for the optimization of the minimal core binding moiety and its linkage to a chem. moiety that imparts substrate specificity. Based on this scaffold, we present a first active de-novo CRBN effector that is able to degrade the neo-substrate IKZF3 in the cell culture. In the experiment, the researchers used many compounds, for example, tert-Butyl (cis-4-(hydroxymethyl)cyclohexyl)carbamate (cas: 223131-01-9Quality Control of tert-Butyl (cis-4-(hydroxymethyl)cyclohexyl)carbamate).

tert-Butyl (cis-4-(hydroxymethyl)cyclohexyl)carbamate (cas: 223131-01-9) 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. 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.Quality Control of tert-Butyl (cis-4-(hydroxymethyl)cyclohexyl)carbamate

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