Category: ethers-buliding-blocks

Efficient synthesis of 6-(hetero)arylthieno[3,2-b]pyridines by Suzuki-Miyaura coupling. Evaluation of growth inhibition on human tumor cell lines, SARs and effects on the cell cycle was written by Queiroz, Maria-Joao R. P.;Calhelha, Ricardo C.;Vale-Silva, Luis A.;Pinto, Eugenia;Lima, Raquel T.;Vasconcelos, M. Helena. And the article was included in European Journal of Medicinal Chemistry in 2010.Synthetic Route of C14H21BO4 This article mentions the following:

A wide variety of new bi(hetero)aryl derivatives of the thieno[3,2-b]pyridine skeleton was obtained in high to excellent yields (65-91%) by Suzuki-Miyaura cross-coupling of the Me 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by us, with aryl or heteroaryl pinacolboranes or potassium trifluoroborates. The coupling products obtained were evaluated for their growth inhibitory effect on three human tumor cell lines, representing different tumor models, MCF-7 (breast adenocarcinoma), A375-C5 (melanoma) and NCI-H460 (non-small cell lung cancer). Some of the compounds showed an interesting activity against the tested cell lines, with GI₅₀ values in the 婵炴挾鎷?range, and it was possible to establish some structure-activity relationships (SARs). Several compounds presented GI₅₀ values below 15 婵炴挾鎷? particularly a bithiophene and an o-aniline thienopyridine derivative The first presented selectivity for MCF-7 and NCI-H460 cell lines, with very low GI₅₀ values (0.7-1.0 婵炴挾鎷?, while the latter was active against the three cell lines tested in this study, also presenting very low GI₅₀ values (2.5-4.2 婵炴挾鎷?. The effect of these two compounds on cell cycle progression was analyzed in the NCI-H460 cell line. Results showed that both compounds interfered with the normal cell cycle distribution. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Synthetic Route of C14H21BO4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O闂佺偨鍎插?or N闂佺偨鍎插?bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Synthetic Route of C14H21BO4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Formation of organometallic species from complexes of N-phenylaza-crown ether conjugates with lead cations in CID-MS/MS conditions was written by Franski, Rafal;Ogorek, Katarzyna;Gierczyk, Blazej. And the article was included in International Journal of Mass Spectrometry in 2017.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

Gas phase decomposition of the ions [M + PbNO₃]⁺ (M stands for fluoro-substituted N-nitrophenylaza-crown ether conjugate), has been studied by the electrospray ionization-collision induced dissociation-tandem mass spectrometry (ESI-CID-MS/MS). The conjugates containing hydrogen atom at ortho position to the crown moiety, form abundant fragment ions which can be assigned as complexes of deprotonated conjugates and lead cation, thus the ions [M – H + Pb]⁺ (fragment ions formed as a result of HNO₃ loss). Interaction between the nitro group (present at the second ortho position to the crown moiety) and the metal cation affects the formation of fragment ion [M – H + Pb]⁺ (but does not prevent its formation). Ions [M – H + Pb]⁺ are very rare example of the organometallic species (containing metal-carbon bond), in which metal cation is also complexed by crown ether moiety. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Safety of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Metal-free reduction of unsaturated carbonyls, quinones, and pyridinium salts with tetrahydroxydiboron/water was written by Peng, Henian;Li, Tiejun;Tian, Duanshuai;Yang, He;Xu, Guangqing;Tang, Wenjun. And the article was included in Organic & Biomolecular Chemistry in 2021.HPLC of Formula: 605-94-7 This article mentions the following:

A series of unsaturated carbonyls, quinones and pyridinium salts were effectively reduced to the corresponding saturated carbonyls, dihydroxybenzenes and di- and tetrahydropyridines in moderate to high yields with tetrahydroxydiboron/water as a mild, convenient and metal-free reduction system. Deuterium-labeling experiments revealed this protocol to be an exclusive transfer hydrogenation process from water. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7HPLC of Formula: 605-94-7).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).HPLC of Formula: 605-94-7

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis and antiviral activity of lycorine derivatives was written by Yang, Ya-Jun;Liu, Jiang-Ning;Pan, Xian-Dao. And the article was included in Journal of Asian Natural Products Research in 2020.COA of Formula: C9H10O4 This article mentions the following:

There are no effective antiviral drugs to treat hand, foot, and mouth disease. In this study, a series of lycorine derivatives were synthesized and evaluated against enterovirus 71 and coxsackievirus A16 in vitro. Derivatives with the phenoxyacyl group at the C-1 position showed higher efficacy and lower toxicity than lycorine. In addition, derivative enhanced the survival rate to 40% in the mouse model of the lethal EV71 infection. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4COA of Formula: C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. Ethyl ether is an excellent solvent for extractions and for a wide variety of chemical reactions. It is also used as a volatile starting fluid for diesel engines and gasoline engines in cold weather. Dimethyl ether is used as a spray propellant and refrigerant. Methyl t-butyl ether (MTBE) is a gasoline additive that boosts the octane number and reduces the amount of nitrogen-oxide pollutants in the exhaust. The ethers of ethylene glycol are used as solvents and plasticizers.COA of Formula: C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Copper-Catalyzed Regioselective Olefination and Trifluoromethylation of Carboxylic Acids To Give (Z)-Trifluoromethyl Enol Esters was written by Lu, Dong;Li, Shuangshuang;Yang, Xiaogang;Yin, Shuang-Feng;Kambe, Nobuaki;Qiu, Renhua. And the article was included in Organic Letters in 2022.Electric Literature of C9H10O4 This article mentions the following:

A method to produce (Z)-trifluoromethyl enol esters via the olefination and trifluoromethylation of carboxylic acids with TMSCF₃ was reported. This synthetic method used inexpensive and easy-to-handle TMSCF₃. It employed a com. available CuCl catalyst to transform a broad range of carboxylic acids into versatile (Z)-trifluoromethyl enol esters with good regio- and stereoselectivity. This protocol allowed the concise synthesis of highly functionalized (Z)-trifluoromethyl enol esters directly from carboxylic acids. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Electric Literature of C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Electric Literature of C9H10O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthesis of monoazacrown ethers under phase-transfer catalysis was written by Luk’yanenko, N. G.;Basok, S. S.;Kulygina, E. Yu.;Bogashchenko, T. Yu.;Yakovenko, I. S.. And the article was included in Russian Journal of Organic Chemistry in 2012.Related Products of 66943-05-3 This article mentions the following:

A procedure was proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol)-bis(p-toluene)sulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzyl-aza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4-10 equiv of LiCl, BaBr₂, and CsCl, resp., to the reaction mixture, which probably indicated template effect. In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Related Products of 66943-05-3).

1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Related Products of 66943-05-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling was written by Chen, Yiding;Willis, Michael C.. And the article was included in Chemical Science in 2017.Category: ethers-buliding-blocks This article mentions the following:

By using a simple copper(I) catalyst a high yielding sulfonylative-Suzuki-Miyaura cross-coupling reaction was developed. The process provided a single step route to diaryl sulfones from the direct combination of arylboronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide was delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulted in the formation of a presumed Cu-sulfinate intermediate. These sulfinates was trapped as their sodium salts and treated with electrophiles to allow access to arylalkyl sulfones, 閻?hydroxyl sulfones, sulfonamides and sulfonyl fluorides. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Category: ethers-buliding-blocks).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Rapid epoxy cure and transamination behavior in vinylogous urethane epoxy using glyme-metal ions was written by Shin, Jaeho;Yi, Mobeom;Kim, Hyunjoong. And the article was included in Koen Yoshishu – Nippon Setchaku Gakkai Nenji Taikai in 2021.Electric Literature of C8H18O4 This article mentions the following:

Here we fabricated three different types of ILs containing lithium or zinc ligand with glyme mol. The unique functions of ionic liquids to intervene oxirane and carbonyl oxygen made the metal-glyme mixture a potential latent cure accelerator in epoxy cure reaction and a catalyst of transamination reaction at the same time. In the experiment, the researchers used many compounds, for example, 2,5,8,11-Tetraoxadodecane (cas: 112-49-2Electric Literature of C8H18O4).

2,5,8,11-Tetraoxadodecane (cas: 112-49-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Electric Literature of C8H18O4

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Efficient Synthesis of Imines by Oxidative Coupling Catalyzed by Ce-Mn Oxide Microspheres was written by Chutimasakul, Threeraphat;Tirdtrakool, Warinda;Na Nakhonpanom, Pakamon;Kreethatorn, Hemmarat;Jaruwatee, Pattamaporn;Bunchuay, Thanthapatra;Tantirungrotechai, Jonggol. And the article was included in ChemistrySelect in 2022.Safety of (4-Methoxyphenyl)methanol This article mentions the following:

Oxidative self-coupling of amines and cross-coupling with alcs. are important reactions for the synthesis of imines; however, catalytic systems for these reactions usually require expensive oxidant, complicated catalyst preparation, complex reaction set-up, and/or additives such as bases or cocatalysts. Here, authors report that amorphous cerium-manganese (Ce-Mn) oxides with hierarchical microsphere structure prepared by a facile method could exhibit excellent catalytic performance for the synthesis of various imines using air as the green oxidant under mild conditions. The Ce-Mn oxide heterogeneous catalysts could also be easily recovered and efficiently recycled without significant loss of activities. The excellent activities and the reusability of the Ce-Mn oxide microspheres offer potential advances in the synthesis of imine. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Safety of (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Safety of (4-Methoxyphenyl)methanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Discovery of Novel, Potent Inhibitors of Hydroxy Acid Oxidase 1 (HAO1) Using DNA-Encoded Chemical Library Screening was written by Lee, Esther C. Y.;McRiner, Andrew J.;Georgiadis, Katy E.;Liu, Julie;Wang, Zooey;Ferguson, Andrew D.;Levin, Benjamin;von Rechenberg, Moritz;Hupp, Christopher D.;Monteiro, Michael I.;Keefe, Anthony D.;Olszewski, Allison;Eyermann, Charles J.;Centrella, Paolo;Liu, Yanbin;Arora, Shilpi;Cuozzo, John W.;Zhang, Ying;Clark, Matthew A.;Huguet, Christelle;Kohlmann, Anna. And the article was included in Journal of Medicinal Chemistry in 2021.Category: ethers-buliding-blocks This article mentions the following:

Inhibition of hydroxy acid oxidase 1 (HAO1) is a strategy to mitigate the accumulation of toxic oxalate that results from reduced activity of alanine-glyoxylate aminotransferase (AGXT) in primary hyperoxaluria 1 (PH1) patients. DNA-Encoded Chem. Library (DECL) screening provided two novel chem. series of potent HAO1 inhibitors, represented by compounds 3-6. Compound I was further optimized via various structure-activity relationship (SAR) exploration methods to II, a compound with improved potency and absorption, distribution, metabolism, and excretion (ADME)/pharmacokinetic (PK) properties. Since carboxylic acid-containing compounds are often poorly permeable and have potential active glucuronide metabolites, we undertook a brief, initial exploration of acid replacements with the aim of identifying non-acid-containing HAO1 inhibitors. Structure-based drug design initiated with Compound I led to the identification of a nonacid inhibitor of HAO1, III, which has weaker potency and increased permeability. In the experiment, the researchers used many compounds, for example, 3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5Category: ethers-buliding-blocks).

3-Formyl-2-methoxyphenylboronic acid (cas: 480424-49-5) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers feature bent C闂佺偨鍎茶ぐ濠囨煃閵夛箑鐤?linkages. In dimethyl ether, the bond angle is 111闁?and C闂佺偨鍎茶ぐ?distances are 141 pm. The barrier to rotation about the C闂佺偨鍎茶ぐ?bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Category: ethers-buliding-blocks

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem