Category: ethers-buliding-blocks

Anti-inflammatory effects of an optimized PPAR-绾?agonist via NF-榄廈 pathway inhibition was written by Ju, Zhiran;Su, Mingzhi;Hong, Jongki;Kim, Eun La;Jung, Jee H.. And the article was included in Bioorganic Chemistry in 2020.Formula: C5H12O3 This article mentions the following:

In our previous study, a PPAR-绾?agonist (+)-(R,E)-6a1 was elaborated as an anti-inflammatory lead. However, in silico anal. showed that (+)-(R,E)-6a1 lacks key hydrogen bonding with Tyr⁴⁷³ of PPAR-绾?LBD (ligand binding domain). To facilitate addnl. hydrogen bonding with Tyr⁴⁷³, a more polar head group was introduced to the structure of (+)-(R,E)-6a1, and we also attempted to synthesize enzymically stable derivatives Of the synthetic derivatives, compound (+)-(R,E)-5f showed highest PPAR-绾?transcriptional activity and reasonable metabolic stability. Compound (+)-(R,E)-5f suppressed the expression of pro-inflammatory mediators such as inducible NO synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin 6 (IL-6), and tumor necrosis factor-浼?(TNF-浼?. Reduction of nitric oxide (NO), and ROS was also observed Compound (+)-(R,E)-5f was found to suppress the NF-榄廈 pathway by inhibiting phosphorylation of IKK (I榄廈 kinase), and this may lead to subsequent inhibition of I榄廈浼?(inhibitor of NF-榄廈浼? phosphorylation and inhibition of NF-榄廈 activation. These results indicate that (+)-(R,E)-5f exerts anti-inflammatory activity via NF-榄廈 pathway inhibition, and may serve as a potential anti-inflammatory lead. In the experiment, the researchers used many compounds, for example, 2-(2-Methoxyethoxy)ethanol (cas: 111-77-3Formula: C5H12O3).

2-(2-Methoxyethoxy)ethanol (cas: 111-77-3) 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閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Formula: C5H12O3

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

New semi-synthetic analogs of oleuropein show improved anticancer activity in vitro and in vivo was written by Samara, Pinelopi;Christoforidou, Nikoleta;Lemus, Christelle;Argyropoulou, Aikaterini;Ioannou, Kyriaki;Vougogiannopoulou, Konstantina;Aligiannis, Nektarios;Paronis, Efthimios;Gaboriaud-Kolar, Nicolas;Tsitsilonis, Ourania;Skaltsounis, Alexios-Leandros. And the article was included in European Journal of Medicinal Chemistry in 2017.Related Products of 3929-47-3 This article mentions the following:

Oleuropein is a glucosylated seco-iridoid present in olive fruits and leaves. Due to its broad spectrum of biol. activities, including anticancer properties, oleuropein has attracted scientific attention for the past 20 years. The promising antiproliferative activity of an olive leaf extract enriched in oleuropein against a series of human cancer cell lines, prompted us to proceed with the semi-synthesis of 51 analogs of oleuropein. Following their initial screening against the estrogen receptor neg. breast cancer cell line SKBR3, 7 analogs were shown to display significant cytotoxicity and were further tested against 6 addnl. solid tumor-derived and leukemic cell lines. The analog with the most promising antitumor activity (24) was selected for more detailed studies. 24 was non-toxic to peripheral blood mononuclear cells derived from healthy blood donors when tested at concentrations close to its half maximal inhibitory concentration In vivo administration of 24 in melanoma-bearing mice resulted in reducing tumor size in a dose-dependent manner and in inducing anti-melanoma-reactive immune responses. Our results suggest that analog 24, emerging from the initial structure of oleuropein, represents a promising lead structure for further optimization. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Related Products of 3929-47-3).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. 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).Related Products of 3929-47-3

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

Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study was written by Thanigaimalai, Pillaiyar;Konno, Sho;Yamamoto, Takehito;Koiwai, Yuji;Taguchi, Akihiro;Takayama, Kentaro;Yakushiji, Fumika;Akaji, Kenichi;Kiso, Yoshiaki;Kawasaki, Yuko;Chen, Shen-En;Naser-Tavakolian, Aurash;Schon, Arne;Freire, Ernesto;Hayashi, Yoshio. And the article was included in European Journal of Medicinal Chemistry in 2013.Formula: C9H10O4 This article mentions the following:

This work describes the design, synthesis, and evaluation of low-mol. weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(pyrrolidone-3-yl)-2-benzothiazole (I) (K_i = 4.1 nM), in which the P3 valine unit was substituted with a variety of distinct moieties. The resulting series of dipeptide-type inhibitors displayed moderate to good inhibitory activities against 3CL^pro. In particular, compounds (II) (R¹ = OMe, R² = H and R¹ = H, R² = OMe) exhibited good inhibitory activities with K_i values of 0.39 and 0.33 娓璏, resp. These low-mol. weight compounds are attractive leads for the further development of potent peptidomimetic inhibitors with pharmaceutical profiles. Docking studies were performed to model the binding interaction of the compound II (R¹ = OMe, R² = H) with the SARS-CoV 3CL protease. The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1′ position, (ii) a 绾?lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the N-arylglycine unit and a backbone hydrogen bond donor at the S3-position. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4Formula: C9H10O4).

2-(4-Methoxyphenoxy)acetic acid (cas: 1877-75-4) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O閳ユ椊 or N閳ユ椊 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.Formula: C9H10O4

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

Synthesis and Photophysics of Fully 锜?Conjugated Heterobis-Functionalized Polymeric Molecular Wires via Suzuki Chain-Growth Polymerization was written by Elmalem, Einat;Biedermann, Frank;Johnson, Kerr;Friend, Richard H.;Huck, Wilhelm T. S.. And the article was included in Journal of the American Chemical Society in 2012.Electric Literature of C14H21BO4 This article mentions the following:

Fully 锜?conjugated polymers of 2-bromo-9,9-dioctylfluoren-2-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with with d.p. up to 23 and near quant. (>95%) heterobis-functionalization are prepared by a controlled Suzuki chain-growth polymerization, with control over mol. weight, narrow polydispersity, and ability to define polymer end groups. The first end group is introduced through the initiator metal complex tert-Bu₃PPd(X)Br (X = aryl), while the second end group is added by quenching of the chain-growth polymerization with the desired boronic esters. In all cases, polymers obtained at 50% conversion showed excellent end group fidelity and high purity following a simple workup procedure, as determined by MALDI-TOF, GPC, and ¹H and 2D NMR. End group functionalization altered the optoelectronic properties of the bridge polymer. Building on a common fluorene backbone, and guided by DFT calculations, donor and acceptor end groups introduced to create polymeric mol. wires exhibiting charge transfer and energy transfer as characterized by fluorescence, absorption, and transient absorption spectroscopy as well as by fluorescence lifetime measurements. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Electric Literature of C14H21BO4).

2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) 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. 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 C14H21BO4

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

para-C-H Borylation of benzene derivatives by a bulky iridium catalyst was written by Saito, Yutaro;Segawa, Yasutomo;Itami, Kenichiro. And the article was included in Journal of the American Chemical Society in 2015.Name: 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

A highly para-selective aromatic C-H borylation has been accomplished. By a new iridium catalyst bearing a bulky diphosphine ligand, Xyl-MeO-BIPHEP, the C-H borylation of monosubstituted benzenes can be affected with para-selectivity up to 91%. This catalytic system is quite different from the usual iridium catalysts that cannot distinguish meta- and para-C-H bonds of monosubstituted benzene derivatives, resulting in the preferred formation of meta-products. The para-selectivity increases with increasing bulkiness of the substituent on the arene, indicating that the regioselectivity of the present reaction is primarily controlled by steric repulsion between substrate and catalyst. Caramiphen, an anticholinergic drug used in the treatment of Parkinson’s disease, was converted into five derivatives via our para-selective borylation. The present [Ir(cod)OH]₂/Xyl-MeO-BIPHEP catalyst represents a unique, sterically controlled, para-selective, aromatic C-H borylation system that should find use in streamlined, predictable chem. synthesis and in the rapid discovery and optimization of pharmaceuticals and materials. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Name: 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

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. 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.Name: 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

Copper-Catalyzed Regioselective Iodoformylation of Terminal Alkynes to Access Versatile Electrophiles (E)-灏?Iodo-浼?灏?Unsaturated Aldehydes was written by Lu, Dong;Yang, Xiaogang;Guan, Wenjian;Yin, Shuang-Feng;Kambe, Nobuaki;Qiu, Renhua. And the article was included in Organic Letters in 2022.Application In Synthesis of (4-Methoxyphenyl)methanol This article mentions the following:

The authors describe a method for synthesizing (E)-灏?iodo-浼?灏?unsaturated aldehydes via the iodoformylation of terminal alkynes with TMSCF₃ and NaI. This synthetic method uses inexpensive and easy-to-handle chem. feedstocks and employs a com. available CuI catalyst. It can transform a broad range of terminal alkynes into bis-electrophile (E)-灏?iodo-浼?灏?unsaturated aldehydes with excellent chemoselectivity, regioselectivity, and stereoselectivity. Moreover, it was demonstrated that this protocol has abundant organic reactivity. In the experiment, the researchers used many compounds, for example, (4-Methoxyphenyl)methanol (cas: 105-13-5Application In Synthesis of (4-Methoxyphenyl)methanol).

(4-Methoxyphenyl)methanol (cas: 105-13-5) 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. 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.Application In Synthesis of (4-Methoxyphenyl)methanol

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

Rapid analysis of brake fluid uses gas-liquid chromatography was written by Esposito, George G.;Jamison, Robert G.. And the article was included in SAE Journal in 1971.Application In Synthesis of 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol This article mentions the following:

The volatile compounds making up 70-80% of most hydraulic brake fluid can be identified and determined by gas chromatog. on a 20 weight % Carbowax 20M/Chromosorb W or a 20 weight % diethylene glycol succinate/Chromosorb W column, by using ethylene glycol monoethyl ether acetate internal standard, a thermal conductivity detector, and He carrier gas. Retention data are given for 36 compounds Anal. of a synthetic composition gave [component, weight % added, weight % found]: ethylene glycol monoethyl ether, 25.0, 24.8; methoxybutanol, 10.0, 12.0; diethylene glycol monoethyl ether, 24.0, 23.5; diethylene glycol monobutyl ether, 11.0, 10.7; base lubricant (by difference), 30.0, 29.0. In the experiment, the researchers used many compounds, for example, 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8Application In Synthesis of 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol).

1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol (cas: 20324-33-8) belongs to ethers. 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. 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.Application In Synthesis of 1-((1-((1-Methoxypropan-2-yl)oxy)propan-2-yl)oxy)propan-2-ol

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

An effective hydrosilylation of alkynes in supercritical CO₂ – A green approach to alkenyl silanes was written by Stefanowska, Kinga;Franczyk, Adrian;Szyling, Jakub;Salamon, Katarzyna;Marciniec, Bogdan;Walkowiak, Jedrzej. And the article was included in Journal of Catalysis in 2017.Reference of 16356-02-8 This article mentions the following:

Hydrosilylation of a wide group of alkynes (terminal and internal) with four structurally different silanes was for the 1st time performed in supercritical CO₂ (scCO₂). The results clearly showed the advantages as well as the limitations of using of scCO₂ as a reaction and extraction medium for hydrosilylation of numerous alkynes with different functionality and volatility. Procedures for the synthesis and isolation of over forty silyl ethenes were described, among which more than twenty for the 1st time. Obtained products were fully characterized by ¹H, ¹³C, ²⁹Si NMR, GC-MS, and EA. Also, by x-ray crystallog., the mol. structures of (E)-3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)-2,5-dimethylhex-3-ene-2,5-diol (3n) and (E)-triethyl(2-(triphenylsilyl)vinyl)silane (12a) were determined for the 1st time. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8Reference of 16356-02-8).

1,4-Dimethoxy-2-butyne (cas: 16356-02-8) 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. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Reference of 16356-02-8

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

Directed assembly of defined oligomeric photosynthetic reaction centres through adaptation with programmable extra-membrane coiled-coil interfaces was written by Swainsbury, David J. K.;Harniman, Robert L.;Di Bartolo, Natalie D.;Liu, Juntai;Harper, William F. M.;Corrie, Alexander S.;Jones, Michael R.. And the article was included in Biochimica et Biophysica Acta, Bioenergetics in 2016.Synthetic Route of C9H10O4 This article mentions the following:

A challenge associated with the utilization of bioenergetic proteins in new, synthetic energy transducing systems is achieving efficient and predictable self-assembly of individual components, both natural and man-made, into a functioning macromol. system. Despite progress with water-soluble proteins, the challenge of programming self-assembly of integral membrane proteins into non-native macromol. architectures remains largely unexplored. In this work it is shown that the assembly of dimers, trimers or tetramers of the naturally monomeric purple bacterial reaction center can be directed by augmentation with an 浼?helical peptide that self-associates into extra-membrane coiled-coil bundle. Despite this induced oligomerization the assembled reaction centers displayed normal spectroscopic properties, implying preserved structural and functional integrity. Mixing of two reaction centers modified with mutually complementary 浼?helical peptides enabled the assembly of heterodimers in vitro, pointing to a generic strategy for assembling hetero-oligomeric complexes from diverse modified or synthetic components_. Addition of two coiled-coil peptides per reaction center monomer was also tolerated despite the challenge presented to the pigment-protein assembly machinery of introducing multiple self-associating sequences. These findings point to a generalized approach where oligomers or longer range assemblies of multiple light harvesting and/or redox proteins can be constructed in a manner that can be genetically-encoded, enabling the construction of new, designed bioenergetic systems in vivo or in vitro. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Synthetic Route of C9H10O4).

2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O閳ユ椊 or N閳ユ椊 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 C9H10O4

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

Production of secondary metabolites including a new metabolite p-methoxyphenylpropanol by the brown-rot fungus Lentinus lepideus was written by Ohta, Akira;Shimada, Mikio;Hattori, Takefumi;Higuchi, Takayoshi;Takahashi, Munezoh. And the article was included in Mokuzai Gakkaishi in 1990.Safety of 3-(3,4-Dimethoxyphenyl)propan-1-ol This article mentions the following:

The secondary metabolites which were biosynthesized from glucose by the brown-rot fungus L. lepideus grown in cultures with varying amounts of nitrogen nutrients were determined The low nitrogen concentration culture produced much greater amounts of the metabolites per nitrogen gram unit than did the high nitrogen concentration culture. A new secondary metabolite, p-methoxyphenylpropanol, was isolated from the cultures of this fungus. Incubation of the cultures with p-coumaric acid, p-methoxycinnamic acid, ferulic acid, isoferulic acid, and Me ferulate yielded a variety of phenylpropanol derivatives A possible biosynthetic route for p-methoxyphenylpropanol is discussed. Among 75 species of white-rot and brown-rot fungi examined, only the brown-rot fungus Daedalea鑱?em>dickinsii produced Me p-methoxycinnamate. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Safety of 3-(3,4-Dimethoxyphenyl)propan-1-ol).

3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 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.Safety of 3-(3,4-Dimethoxyphenyl)propan-1-ol

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