Category: ethers-buliding-blocks

Discovery of 5-bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives as novel ULK1 inhibitors that block autophagy and induce apoptosis in non-small cell lung cancer was written by Sun, Dejuan;Yang, Zijian;Zhen, Yongqi;Yang, Yushang;Chen, Yanmei;Yuan, Yong;Zhang, Lan;Zeng, Xiaoxi;Chen, Lixia. And the article was included in European Journal of Medicinal Chemistry in 2020.Recommanded Product: 4-Benzyloxyphenol The following contents are mentioned in the article:

5-Bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives were synthesized and evaluated as ULK1 inhibitors in non-small cell lung cancer. Among all the obtained ULK1 inhibitors, 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine, was the most active one. The docking anal. was conducted to compare 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine and SBI-0206965, which further elucidated the roles of the H-bond donor. This compound inhibited the proliferation of A549 cells and showed strong inhibitory activity against ULK1 kinase. Moreover, we found that 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine could induce apoptosis while simultaneously blocking autophagy. Collectively, these findings shed new light on 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine that would be utilized as a promising candidate drug for the future NSCLC therapy. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Recommanded Product: 4-Benzyloxyphenol).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: 4-Benzyloxyphenol

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

Discovery of 5-bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives as novel ULK1 inhibitors that block autophagy and induce apoptosis in non-small cell lung cancer was written by Sun, Dejuan;Yang, Zijian;Zhen, Yongqi;Yang, Yushang;Chen, Yanmei;Yuan, Yong;Zhang, Lan;Zeng, Xiaoxi;Chen, Lixia. And the article was included in European Journal of Medicinal Chemistry in 2020.Recommanded Product: 4-Benzyloxyphenol The following contents are mentioned in the article:

5-Bromo-4-phenoxy-N-phenylpyrimidin-2-amine derivatives were synthesized and evaluated as ULK1 inhibitors in non-small cell lung cancer. Among all the obtained ULK1 inhibitors, 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine, was the most active one. The docking anal. was conducted to compare 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine and SBI-0206965, which further elucidated the roles of the H-bond donor. This compound inhibited the proliferation of A549 cells and showed strong inhibitory activity against ULK1 kinase. Moreover, we found that 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine could induce apoptosis while simultaneously blocking autophagy. Collectively, these findings shed new light on 5-bromo-4-(2-fluoro-4-nitrophenoxy)-N-(3,4,5-trimethoxyphenyl) pyrimidin-2-amine that would be utilized as a promising candidate drug for the future NSCLC therapy. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Recommanded Product: 4-Benzyloxyphenol).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Recommanded Product: 4-Benzyloxyphenol

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

Asymmetric Synthesis of 3-Pyrrolines through an Aryne-Induced Domino Process was written by Hwu, Jih Ru;Panja, Avijit;Gupta, Nitesh K.;Huang, Wen-Chieh;Hu, Yu-Chen;Lin, Chun-Cheng;Hwang, Kuo-Chu;Chan, Wei-Jen;Tsay, Shwu-Chen. And the article was included in Asian Journal of Organic Chemistry in 2021.Computed Properties of C3H9NO The following contents are mentioned in the article:

Here, the accomplishment of a newly developed domino reaction was reported for synthesizing optically active 3-pyrrolines I [R¹ = H, OMe, OCH₂O; R² = H, p-Me, p-OMe, m-Br; R³ = OMe, CN, CO₂Me; R⁴ = CO₂Me, CO₂Et; R⁵ = H, CO₂Me, CO₂Et], a class of compounds with various biol. properties. The reaction involved the use of (trimethylsilyl)aryl triflates, Schiff bases, and alkynes in the presence of a chiral catalyst (R)-(-)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate. The key features of this new reaction include the generation of a single product in very good yields (75-85%) with high stereo- and enantio-selectivity; the enantiomeric ratio reaches as high as 98.5 : 1.5. Moreover, it involved an aryne-induced domino reaction and an unusual 1,4-intramol. proton transfer, which overwhelms the well-established 1,5-proton transfer. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Computed Properties of C3H9NO).

2-Methoxyethylamine (cas: 109-85-3) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Computed Properties of C3H9NO

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

Microwave-assisted synthesis of silver nanoprisms/nanoplates using a “modified polyol process” was written by Darmanin, Thierry;Nativo, Paola;Gilliland, Douglas;Ceccone, Giacomo;Pascual, Cesar;De Berardis, Barbara;Guittard, Frederic;Rossi, Francois. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2012.Safety of 2-(2-(Hexyloxy)ethoxy)ethanol The following contents are mentioned in the article:

In this paper, we report a novel, efficient and versatile process to produce high concentrations of silver nanoprisms, while controlling their size (prism height) and size dispersity, using a “modified polyol process” (microwave-assisted process). If the formation of silver spherical particles, nanocubes or nanowires has already been reported using the classical polyol process (reduction of AgNO₃ by ethylene glycol and in presence of PVP), here we show that the production of silver nanoprisms/nanoplates is possible by a careful choice in the process parameters and in particular in the reducing agent (ethylene glycol should be replaced by a reducing agent containing only one hydroxyl reducing group such as ethylene glycol monoalkyl ethers). The synthesis, characterization, the influence of parameters and the mechanism of formation are discussed in order to correlate the operational conditions with the shape and the dimension of the nanoparticles. This study involved multiple reactions and reactants, such as 2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4Safety of 2-(2-(Hexyloxy)ethoxy)ethanol).

2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Safety of 2-(2-(Hexyloxy)ethoxy)ethanol

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

Cell-Based Drug Discovery: Identification and Optimization of Small Molecules that Reduce c-MYC Protein Levels in Cells was written by Medina, Jesus R.;Tian, Xinrong;Li, William H.;Suarez, Dominic;Mack, James F.;LaFrance, Louis;Martyr, Cuthbert;Brackley, James;Di Marco, Christina;Rivero, Ralph;Heerding, Dirk A.;McHugh, Charles;Minthorn, Elisabeth;Bhaskar, Aishwarya;Rubin, Jacob;Butticello, Michael;Carpenter, Christopher;Nartey, Eldridge N.;Berrodin, Thomas J.;Kallal, Lorena A.;Mangatt, Biju. And the article was included in Journal of Medicinal Chemistry in 2021.Computed Properties of C3H9NO The following contents are mentioned in the article:

Elevated expression of the c-MYC oncogene is one of the most common abnormalities in human cancers. Unfortunately, efforts to identify pharmacol. inhibitors that directly target MYC have not yet yielded a drug-like mol. due to the lack of any known small mol. binding pocket in the protein, which could be exploited to disrupt MYC function. We have recently described a strategy to target MYC indirectly, where a screening effort designed to identify compounds that can rapidly decrease endogenous c-MYC protein levels in a MYC-amplified cell line led to the discovery of a compound series that phenocopies c-MYC knockdown by siRNA. Herein, we describe our medicinal chem. program that led to the discovery of potent, orally bioavailable c-MYC-reducing compounds The development of a min. pharmacophore model based on empirical structure activity relationship as well as the property-based approach used to modulate pharmacokinetics properties will be highlighted. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Computed Properties of C3H9NO).

2-Methoxyethylamine (cas: 109-85-3) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Computed Properties of C3H9NO

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

Metabolomics-based profiling for quality assessment and revealing the impact of drying of Turmeric (Curcuma longa L.) was written by Salem, Mohamed A.;El-Shiekh, Riham A.;Fernie, Alisdair R.;Alseekh, Saleh;Zayed, Ahmed. And the article was included in Scientific Reports in 2022.Synthetic Route of C19H16O4 The following contents are mentioned in the article:

Turmeric, the rhizomes of Curcuma longa L., is one of the top selling spices, food preservatives, and food colorants. In addition, it exhibits health promoting benefits owing to its unique phytochem. composition Nevertheless, it is commonly subjected to heat drying, hence, the dried powder is the most used form and can easily be adulterated with allied species. Therefore, our research aimed to profile the phytochem. composition and investigate the impact of drying of turmeric. Extraction and fractionation followed by LC- and GC-MS anal. resulted in the identification of a total of 161 metabolites belonged to various phytochem. classes. Moreover, multivariate data anal. identified curcuminoids, terpecurcumins, and organic acids as potential markers for drying. Based on the applied anal. techniques in combination with chemometrics, these investigations have succeeded to provide good coverage of the metabolome of turmeric in both fresh and dried forms. This study involved multiple reactions and reactants, such as Bisdemethoxycurcumin (cas: 33171-05-0Synthetic Route of C19H16O4).

Bisdemethoxycurcumin (cas: 33171-05-0) belongs to ethers. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Synthetic Route of C19H16O4

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

Nickel Dual Photoredox Catalysis for the Synthesis of Aryl Amines was written by Key, Ryan J.;Vannucci, Aaron K.. And the article was included in Organometallics in 2018.Electric Literature of C12H12N2O The following contents are mentioned in the article:

In this work, a new dual photoredox nickel catalysis system has been utilized for the synthesize of aryl amines. Previously, our group has shown that a nickel catalyst in conjunction with a photosensitizer and a sacrificial electron donor can cross-couple C-C bonds via photoredox-assisted reductive coupling. Here we have built upon that system to develop a redox-neutral cross-coupling system for the formation of C-N bonds. The catalytic system is composed of just a nickel cross-coupling catalyst, a Ru photocatalyst, and base and is capable of coupling amines with aryl halides in good to excellent yields. Furthermore, it was found that these reactions are functional under ambient conditions with catalyst loadings of 1 mol %. Spectroscopic studies provide support that this amination mechanism proceeds via a nitrogen-based radical intermediate. This N-radical mechanism offers direct synthetic access to di- and triaryl amines from nickel photocatalysis. This study involved multiple reactions and reactants, such as N-(4-Methoxyphenyl)pyridin-3-amine (cas: 562085-85-2Electric Literature of C12H12N2O).

N-(4-Methoxyphenyl)pyridin-3-amine (cas: 562085-85-2) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Electric Literature of C12H12N2O

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

Functionalized Triphenylene Discotic Molecules: Synthesis and Mesomorphic Characterizations was written by Srinivasa, H. T.;Hariprasad, S.. And the article was included in ChemistrySelect in 2022.HPLC of Formula: 103-16-2 The following contents are mentioned in the article:

The synthesis and characterization of two sets of triphenylene derived discotic mols. with phenol, aldehyde and acid functional groups was reported. In the first set, triphenylene moiety was tethered with benzene derivatives via an ester linkage, while in the second set via an ether linkage with increased aromatic conjugation. All the mols. have triphenylene disk at one end and with benzene, biphenyl and terphenyl cores at the other end connected via flexible methylene spacers. The chem. structures of the novel compounds were confirmed by IR, NMR spectroscopy and CHN anal. methods. Thermal and liquid crystal texture properties were determined using differential scanning calorimetry, polarized optical microscope and X-ray diffraction studies. Amongst all the novel compounds, only the terphenyl derivative displayed mesomorphism. However, their charge transfer complexes with trinitrofluorenone (TNF) an electron acceptor exhibited columnar mesophases. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2HPLC of Formula: 103-16-2).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. HPLC of Formula: 103-16-2

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

Functionalized Triphenylene Discotic Molecules: Synthesis and Mesomorphic Characterizations was written by Srinivasa, H. T.;Hariprasad, S.. And the article was included in ChemistrySelect in 2022.HPLC of Formula: 103-16-2 The following contents are mentioned in the article:

The synthesis and characterization of two sets of triphenylene derived discotic mols. with phenol, aldehyde and acid functional groups was reported. In the first set, triphenylene moiety was tethered with benzene derivatives via an ester linkage, while in the second set via an ether linkage with increased aromatic conjugation. All the mols. have triphenylene disk at one end and with benzene, biphenyl and terphenyl cores at the other end connected via flexible methylene spacers. The chem. structures of the novel compounds were confirmed by IR, NMR spectroscopy and CHN anal. methods. Thermal and liquid crystal texture properties were determined using differential scanning calorimetry, polarized optical microscope and X-ray diffraction studies. Amongst all the novel compounds, only the terphenyl derivative displayed mesomorphism. However, their charge transfer complexes with trinitrofluorenone (TNF) an electron acceptor exhibited columnar mesophases. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2HPLC of Formula: 103-16-2).

4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.HPLC of Formula: 103-16-2

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

Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom was written by Tcarkova, K. V.;Belus, S. K.;Artyushin, O. I.;Kharlamov, A. V.;Bondarenko, N. A.. And the article was included in Russian Chemical Bulletin in 2015.Recommanded Product: 2-(2-(Hexyloxy)ethoxy)ethanol The following contents are mentioned in the article:

A series of acyclic sym. quaternary ammonium chlorides Me₂(HOCH₂CH₂)N⁺(CH₂CH₂O)_nR Cl^– (n = 1, R = n-C₉H₁₉; n = 2, R = n-C₆H₁₃; n = 3, R = n-C₃H₇) was synthesized by alkylation of the corresponding tertiary amines Me₂N(CH₂CH₂O)_nR with ethylene chlorohydrin in a two-phase system, using water as a solvent. The tertiary amines were synthesized in a heterogeneous system organic phase-aqueous phase, using an aqueous solution of Me₂NH and a solid alkali. The intermediate monoethers of ethylene, di and triethylene glycol were obtained in high yield via a phase-transfer alkylation in dioxane, using solid KOH. The proton and carbon atom signals in the NMR spectra of the synthesized amines and ammonium chlorides were assigned based on the data of heteronuclear correlations (¹H, ¹³C). This study involved multiple reactions and reactants, such as 2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4Recommanded Product: 2-(2-(Hexyloxy)ethoxy)ethanol).

2-(2-(Hexyloxy)ethoxy)ethanol (cas: 112-59-4) belongs to ethers. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: 2-(2-(Hexyloxy)ethoxy)ethanol

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