Month: January 2023

Synthesis and Biological Evaluation of N-Hydroxyphenylacrylamides and N-Hydroxypyridin-2-ylacrylamides as Novel Histone Deacetylase Inhibitors was written by Thaler, Florian;Colombo, Andrea;Mai, Antonello;Amici, Raffaella;Bigogno, Chiara;Boggio, Roberto;Cappa, Anna;Carrara, Simone;Cataudella, Tiziana;Fusar, Fulvia;Gianti, Eleonora;di Ventimiglia, Samuele Joppolo;Moroni, Maurizio;Munari, Davide;Pain, Gilles;Regalia, Nickolas;Sartori, Luca;Vultaggio, Stefania;Dondio, Giulio;Gagliardi, Stefania;Minucci, Saverio;Mercurio, Ciro;Varasi, Mario. And the article was included in Journal of Medicinal Chemistry in 2010.Quality Control of 2-Bromopyridine-4-methanol This article mentions the following:

The histone deacetylases (HDACs) are able to regulate gene expression, and histone deacetylase inhibitors (HDACi) emerged as a new class of agents in the treatment of cancer as well as other human disorders such as neurodegenerative diseases. In the present investigation, we report on the synthesis and biol. evaluation of compounds derived from the expansion of a HDAC inhibitor scaffold having N-hydroxy-3-phenyl-2-propenamide and N-hydroxy-3-(pyridin-2-yl)-2-propenamide as core structures and containing a phenyloxopropenyl moiety, either unsubstituted or substituted by a 4-methylpiperazin-1-yl or 4-methylpiperazin-1-ylmethyl group. The compounds were evaluated for their ability to inhibit nuclear HDACs, as well as for their in vitro antiproliferative activity. Moreover, their metabolic stability in microsomes and aqueous solubility were studied and selected compounds were further characterized by in vivo pharmacokinetic experiments These compounds showed a remarkable stability in vivo, compared to hydroxamic acid HDAC inhibitors that have already entered clin. trials. The representative compound I showed in vivo antitumor activity in a human colon carcinoma xenograft model. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-4-methanol (cas: 118289-16-0Quality Control of 2-Bromopyridine-4-methanol).

2-Bromopyridine-4-methanol (cas: 118289-16-0) 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.Quality Control of 2-Bromopyridine-4-methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Yellow triazine as an efficient photoinitiator for polymerization and 3D printing under LEDs was written by Lai, H.;Zhu, D.;Xiao, P.. And the article was included in Macromolecular Chemistry and Physics in 2019.SDS of cas: 4074-88-8 This article mentions the following:

The search for new efficient photoinitiators for polymerization under the illumination of visible light is under extensive investigation due to their wide application in 3D printing. 2-(4-Methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine (yellow triazine, R-Cl) alone or the R-Cl/additive systems have been indicated as promising photoinitiating systems in the free radical polymerization at 405 nm in our previous study. Here, further investigation of R-Cl in the polymerization of a series of difunctional (meth)acrylate monomers is described. The effect of monomers on the polymerization performance is elucidated. The interplay of functional group, double bond concentration, and fluidity determines the polymerization rate and final conversions. Remarkably, R-Cl shows better photoinitiating ability than well-known com. photoinitiator bisacylphosphine oxide in the polymerization of bis-GMA/TEGDMA blend and EB605 under LED at 400 nm. The optimum concentrations of R-Cl in the photopolymerization of TetEGDA and DPGDA monomers are revealed, the results of which are used to guide the 3D printing of DPGDA. In the experiment, the researchers used many compounds, for example, Diethyleneglycoldiacrylate (cas: 4074-88-8SDS of cas: 4074-88-8).

Diethyleneglycoldiacrylate (cas: 4074-88-8) 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.SDS of cas: 4074-88-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Powder X-ray diffraction can differentiate between enantiomeric variants of calcium lactate pentahydrate crystal in cheese was written by Tansman, G. F.;Kindstedt, P. S.;Hughes, J. M.. And the article was included in Journal of Dairy Science in 2014.Electric Literature of C6H20CaO11 This article mentions the following:

Powder X-ray diffraction has been used for decades to identify crystals of calcium lactate pentahydrate in Cheddar cheese. According to this method, diffraction patterns are generated from a powd. sample of the crystals and compared with reference cards within a database that contains the diffraction patterns of known crystals. During a preliminary study of crystals harvested from various Cheddar cheese samples, we observed 2 slightly different but distinct diffraction patterns that suggested that calcium lactate pentahydrate may be present in 2 different crystalline forms. We hypothesized that the 2 diffraction patterns corresponded to 2 enantiomeric forms of calcium lactate pentahydrate (L– and DL-) that are believed to occur in Cheddar cheese, based on previous studies involving enzymic analyses of the lactate enantiomers in crystals obtained from Cheddar cheeses. However, the powder X-ray diffraction database currently contains only one reference diffraction card under the title “calcium lactate pentahydrate.”. To resolve this apparent gap in the powder X-ray diffraction database, we generated diffraction patterns from reagent-grade calcium L-lactate pentahydrate and laboratory-synthesized calcium DL-lactate pentahydrate. From the resulting diffraction patterns we determined that the existing reference diffraction card corresponds to calcium DL-lactate pentahydrate and that the other form of calcium lactate pentahydrate observed in cheese crystals corresponds to calcium L-lactate pentahydrate. Therefore, this report presents detailed data from the 2 diffraction patterns, which may be used to prepare 2 reference diffraction cards that differentiate calcium L-lactate pentahydrate from calcium DL-lactate pentahydrate. Furthermore, we collected crystals from the exteriors and interiors of Cheddar cheeses to demonstrate the ability of powder X-ray diffraction to differentiate between the 2 forms of calcium lactate pentahydrate crystals in Cheddar cheeses. Powder X-ray diffraction results were validated using enzymic assays for lactate enantiomers. These results demonstrated that powder X-ray diffraction can be used as a diagnostic tool to quickly identify different forms of calcium lactate pentahydrate that may occur in Cheddar cheese. In the experiment, the researchers used many compounds, for example, Calcium 2-hydroxypropanoate pentahydrate (cas: 5743-47-5Electric Literature of C6H20CaO11).

Calcium 2-hydroxypropanoate pentahydrate (cas: 5743-47-5) 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.Electric Literature of C6H20CaO11

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Allyl 4-Chlorophenyl Sulfone as a Versatile 1,1-Synthon for Sequential α-Alkylation/Cobalt-Catalyzed Allylic Substitution was written by Sekino, Tomoyuki;Sato, Shunta;Kuwabara, Kazuki;Takizawa, Koji;Yoshino, Tatsuhiko;Kojima, Masahiro;Matsunaga, Shigeki. And the article was included in Synthesis in 2020.Name: 2-(4-(Trifluoromethyl)phenyl)ethanol This article mentions the following:

Herein, allyl 4-chlorophenyl sulfone as a versatile linchpin for both base-mediated α-derivatization and subsequent cobalt-catalyzed allylic substitution was identified. The sequential transformations allow for highly regioselective access to branched allylic substitution products with a variety of aliphatic side chains RCH₂CH(CH=CH₂)CH(C(O)OR¹)₂ (R = Me, phenylmethyl, 2-thiophen-2-ylmethyl, etc.; R¹ = Me, Bn, 4-methylphenyl, etc.) and 2-(pent-1-en-3-yl)malononitrile. The photoredox-enabled cobalt catalysis is indispensable for achieving high yields and regioselectivity for the desulfonylative substitution in contrast to traditional metal-catalyzed protocols, which lead to inferior outcomes in the corresponding transformations. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Name: 2-(4-(Trifluoromethyl)phenyl)ethanol).

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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Name: 2-(4-(Trifluoromethyl)phenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Contrasting Anticancer Activity of Half-Sandwich Iridium(III) Complexes Bearing Functionally Diverse 2-Phenylpyridine Ligands was written by Millett, Adam J.;Habtemariam, Abraha;Romero-Canelon, Isolda;Clarkson, Guy J.;Sadler, Peter J.. And the article was included in Organometallics in 2015.COA of Formula: C6H6BrNO This article mentions the following:

We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η⁵-Cp*)Ir(2-(R’-phenyl)-R-pyridine)Cl] bearing either an electron-donating (-OH, -CH₂OH, -CH₃) or electron-withdrawing (-F, -CHO, -NO₂) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η⁵-Cp*)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η⁵-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) exhibit the expected “piano-stool” configuration. DFT calculations showed that substituents caused only localized effects on the electrostatic potential surface of the chelating 2-PhPy ligand of the complexes. Hydrolysis of all complexes is rapid, but readily reversed by addition of NaCl. The complexes show preferential binding to 9-ethylguanine over 9-methyladenine and are active catalysts for the oxidation of NADH to NAD⁺. Antiproliferative activity experiments in A2780 ovarian, MCF-7 breast, A549 lung, and HCT116 colon cancer cell lines showed IC₅₀ values ranging from 1 to 89 μM, with the most potent complex, [(η⁵-Cp*)Ir(2-(2′-methylphenyl)pyridine)Cl] (13) (A2780 IC₅₀ = 1.18 μM), being 10× more active than the parent, [(η⁵-Cp*)Ir(2-phenylpyridine)Cl], and 2× more active than [(η⁵-Cp^xPh)Ir(2-phenylpyridine)Cl]. Intriguingly, contrasting biol. activities are observed between structural isomers despite exhibiting similar chem. reactivity. For pairs of structural isomers both the nature and position of the functional group can affect the hydrophobicity of the complex. An increase in hydrophobicity resulted in enhanced cellular-iridium accumulation in A2780 ovarian cells, which generally gave rise to an increase in potency. The structural isomers [(η⁵-Cp*)Ir(2-(4′-fluorophenyl)pyridine)Cl] (2) and [(η⁵-Cp*)Ir(2-phenyl-5-fluoropyridine)Cl] (4) preferentially localized in the cytosol > membrane and particulate > nucleus > cytoskeleton. This work highlights the strong dependence of biol. behavior on the nature and position of the substituent on the chelating ligand and shows how this class of organometallic anticancer complexes can be fine-tuned to increase their potency without using extended cyclopentadienyl systems. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-4-methanol (cas: 118289-16-0COA of Formula: C6H6BrNO).

2-Bromopyridine-4-methanol (cas: 118289-16-0) 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. 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.COA of Formula: C6H6BrNO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The α-alkylation of ketones with alcohols in pure water catalyzed by a water-soluble Cp*Ir complex bearing a functional ligand was written by Meng, Chong;Xu, Jing;Tang, Yawen;Ai, Yao;Li, Feng. And the article was included in New Journal of Chemistry in 2019.COA of Formula: C7H6Cl2O This article mentions the following:

A water-soluble dinuclear Cp*Ir complex bearing 4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine as a bridging ligand was found to be a highly effective catalyst for the α-alkylation of ketones with alcs. in pure water. In the presence of catalyst (0.5 mol%), a series of desirable products were obtained with high reaction economy under environmentally benign conditions. The importance of the hydroxy group in the ligand for catalytic hydrogen transfer was confirmed by mechanism experiments Furthermore, the application of this catalytic system for the synthesis of a biol. active mol. donepezil in pure water was accomplished. Notably, this research would facilitate the progress of C-C bond-forming reactions in water catalyzed by water-soluble metal-ligand bifunctional catalysts. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8COA of Formula: C7H6Cl2O).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) 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. 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.COA of Formula: C7H6Cl2O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Enantioselective Radical Ring-Opening Cyanation of Oxime Esters by Dual Photoredox and Copper Catalysis was written by Chen, Jun;Wang, Peng-Zi;Lu, Bin;Liang, Dong;Yu, Xiao-Ye;Xiao, Wen-Jing;Chen, Jia-Rong. And the article was included in Organic Letters in 2019.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

Catalytic enantioselective chem. reactions involving highly reactive radical species remain largely unexplored. Herein, for the first time a novel enantioselective radical ring-opening cyanation of redox-active oxime esters by dual photoreodox and copper catalysis is reported. This mild protocol shows good functional group tolerance and broad substrate scope, producing a wide range of optically active alkyl dinitriles with high yields and excellent enantioselectivities, which are difficult to access traditionally. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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. 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.Quality Control of 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Borane evolution and its application to organic synthesis using the phase-vanishing method was written by Soga, Nene;Yoshiki, Tomo;Sato, Aoi;Kawamoto, Takuji;Ryu, Ilhyong;Matsubara, Hiroshi. And the article was included in Tetrahedron Letters in 2021.Safety of 2-(4-(Trifluoromethyl)phenyl)ethanol This article mentions the following:

Although borane is a useful reagent, it is difficult to handle. In this study, borane was generated in situ from NaBH₄ or ⁿBu₄NBH₄ with several oxidants (H₂SO₄, I₂, or EtI) using a phase-vanishing (PV) method using a mixture of a fluorinated solvent (Galden HT-135, Galden HT-200, or FC-72) and a nonfluorinated solvent (DME or THF). The borane generated was directly reacted with alkenes, affording the desired alcs. in good yields after oxidation with H₂O₂ under basic conditions. The selective reduction of carboxylic acids with the evolved borane was examined The organoboranes generated by the PV method successfully underwent Suzuki-Miyaura coupling. Using this PV system, reactions with borane can be carried out easily and safely in a common test tube. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Safety of 2-(4-(Trifluoromethyl)phenyl)ethanol).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) 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. 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.Safety of 2-(4-(Trifluoromethyl)phenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

One dimensional chemical shift modulated correlation spectroscopy of single-crystals was written by Iuliucci, Robbie J.;Grant, David M.. And the article was included in Solid State Nuclear Magnetic Resonance in 1996.Computed Properties of C6H14O6 This article mentions the following:

A simple 1-dimensional modulation method is presented for determining the spatial correlation of chem. shifts in two different single-crystal orientations. This proposed chem. shift modulated correlation (CSMC) spectroscopy uses a Jeener pulse sequence to give 1-dimensional spectra containing peaks that are amplitude modulated by the chem. shifts associated with the single-crystal’s evolution orientation. Conversely, the spectral frequencies in these 1-dimensional CSMC spectra designate the shifts in the crystal’s orientation during the detection period. By observing the amplitude modulation of these spectral frequencies, the spatial correlation between the two chem. environments can be established for a specific nucleus from a single 1-dimensional spectrum. The CSMC procedure finishes by acquiring a normal 1-dimensional static spectrum for the crystal oriented in the evolution direction, thereby providing very accurate evolution frequencies approximated by the amplitude modulation in the CSMC spectra. The CSMC method improves the time efficiency over both the traditional goniometer method and the 2-dimensional chem. shift-chem. shift correlation method, and therefore is beneficial for the study of samples with longer T₁ values. In the experiment, the researchers used many compounds, for example, (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0Computed Properties of C6H14O6).

(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal hydrate (cas: 10030-85-0) 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.Computed Properties of C6H14O6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Light-Triggered, Self-Immolative Nucleic Acid-Drug Nanostructures was written by Tan, Xuyu;Li, Ben B.;Lu, Xueguang;Jia, Fei;Santori, Clarissa;Menon, Priyanka;Li, Hui;Zhang, Bohan;Zhao, Jean J.;Zhang, Ke. And the article was included in Journal of the American Chemical Society in 2015.Synthetic Route of C7H7NO4 This article mentions the following:

The simultaneous intracellular delivery of multiple types of payloads, such as hydrophobic drugs and nucleic acids, typically requires complex carrier systems. Herein, we demonstrate a self-deliverable form of nucleic acid-drug nanostructure that is composed almost entirely of payload mols. Upon light activation, the nanostructure sheds the nucleic acid shell, while the core, which consists of prodrug mols., disintegrates via an irreversible self-immolative process, releasing free drug mols. and small mol. fragments. We demonstrate that the nanostructures exhibit enhanced stability against DNase I compared with free DNA, and that the model drug (camptothecin) released exhibits similar efficacy as free, unmodified drugs toward cancer cells. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Synthetic Route of C7H7NO4).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) 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. 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.Synthetic Route of C7H7NO4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts