Tag: 0-100

The effect of benzenesulfonamide′s side chains on their human carbonic anhydrase I/II inhibitory activities was written by Yang, Chaofu;Sun, Xianyu;Li, Zhan;Cheng, Yunyun;Lei, Yu;Lu, Liang;Liu, Xuan;Zhuang, Xiaomei;Wang, Tao;He, Xinhua. And the article was included in Journal of Molecular Structure in 2022.Quality Control of 2-Methoxyethylamine The following contents are mentioned in the article:

Benzenesulfonamides are well-known potent carbonic anhydrase inhibitors (CAIs). They are usually composed of benzenesulfonamide heads and hydrophobic side chain tails. However, hydrophobic side chain tails contribute to poor water solubility, which is a major challenge in the development of CAIs. Herein, to elaborate whether benzenesulfonamides with hydrophilic/hydrophobic tails are effective against carbonic anhydrases (CAs), 12 benzenesulfonamides containing hydrophilic tails and 16 benzenesulfonamides containing hydrophobic tails were designed and synthesized. Benzenesulfonamides with hydrophilic tails including 4b, 4c, and 5b and benzenesulfonamides with hydrophobic tails including 2e, 4b, and 4c are potent carbonic anhydrase I/II dual inhibitors whose Ki to CA I and CA II were below 10 nM, and below 50 nM, resp. However, the water solubility of 4b, 4c, and 5b was 52, 148, and 71 mg/100 g of water, resp., which is much better than that of benzenesulfonamides with hydrophobic tails. In a hypoxic mouse model, compounds 4c and 5b extended the survival of mice by 34.46% and 28.23%, resp., compared to the blank control. Treatment with 4c and 5b extended survival better than acetazolamide treatment did (16.86%). Moreover, 5b also has better anti-convulsant effect than AAZ. Mol. docking anal. demonstrated that hydrogen bonds between the oxygen atoms in the hydrophilic tails of 4b, 4c, and 5b and H2O in hCA I and hCA II protein facilitated ligand-receptor binding. Therefore, considering the good water solubility and potent CA I/II inhibition, 4c and 5b are worth exploring as therapeutic options for acute mountain sickness. In conclusion, benzenesulfonamides containing hydrophilic tails could offer innovative opportunities for potent, water-soluble anti-AMS (Acute Mountain Sickness) compounds This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Quality Control of 2-Methoxyethylamine).

2-Methoxyethylamine (cas: 109-85-3) 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. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Quality Control of 2-Methoxyethylamine

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

Discovery of benzo[d]isothiazole derivatives as novel scaffold inhibitors targeting the programmed cell death-1/programmed cell death-ligand 1 (PD-1/PD-L1) interaction through “ring fusion” strategy was written by Gao, Yinli;Wang, Hanxun;Shen, Lanlan;Xu, Hanqing;Deng, Minghui;Cheng, Maosheng;Wang, Jian. And the article was included in Bioorganic Chemistry in 2022.COA of Formula: C3H9NO The following contents are mentioned in the article:

The inhibition of programmed cell death-1/programmed cell death-ligand 1 (PD-1/PD-L1) interaction by monoclonal antibodies (mAbs) has achieved promising outcomes in cancer immunotherapy. Due to the inherent deficiencies of mAbs drugs, such as high cost of treatment, immunogenicity, poor pharmacokinetics and penetration of solid tumors, researchers are encouraged to develop small mol. inhibitors, to overcome mAbs drugs deficiencies and change the situation where small mol. drugs are not available on the market. Herein, we reported a series of benzo[d]isothiazole derivatives targeting the PD-1/PD-L1 interaction through “ring fusion” strategy using BMS-202 as a starting point. Among them, compound (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine exhibited the best inhibitory activity with an IC₅₀ value of 5.7 nM by homogeneous time-resolved fluorescence (HTRF) binding assay. In immunotoxicity anal., (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine showed low cytotoxicity to Jurkat T cells in CCK-8 assay compared to BMS-202. The binding mode between (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine and PD-L1 protein was explored by mol. docking and mol. dynamics (MD) simulations, which revealed crucial chem. groups, such as biphenyl group interacting with Ile54A, Tyr56A, Met115A, Ala121A, Ile54B, Met115B, Ala121B and Tyr123B by hydrophobic interactions, bromobenzene moiety forming π-π stacking interaction with Tyr56B, as well as L-serine moiety forming hydrogen bond (H-bond) and salt bridge interactions with Asp122A and Lys124A. Furthermore, mol. modeling studies showed that (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine is likely to bind to the FA8 (fatty acid 8) binding site of human serum albumin (HSA). Taken together, (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine significantly inhibits the PD-1/PD-L1 interaction with low cytotoxicity, indicating that (3-bromo-4-((7-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)benzo[d] isothiazol-3-yl)amino)benzyl)-L-serine is a promising starting point for further drug development in cancer immunotherapy. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3COA of Formula: 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.COA of Formula: C3H9NO

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

Investigation of the temperature responsive behaviors of novel polyaspartamide derivatives bearing alkyl ether-type pendants was written by Zhang, Guangyan;Bao, Chenhui;Yi, Hui. And the article was included in Arabian Journal of Chemistry in 2021.Product Details of 109-85-3 The following contents are mentioned in the article:

Previous works reported that some temperature responsive polyaspartamide derivatives exhibited pH responsiveness, although pH responsive functional groups or pH-cleavable linkages were not introduced during the preparing process, which may be related to the hydroxyl groups of their pendant alkanolamide moieties. In order to investigate whether pH will also affect the temperature responsive behavior of temperature responsive polyaspartamide derivatives without hydroxyl groups, four linear alkyl ether-type amine compounds with one ether oxygen atom and 3 to 6 carbon atoms, denoted as OCx (x represents the number of carbon atoms in alkyl ether-type amine compounds), were selected for the aminolysis reaction of poly(succinimide) to design and synthesize the polyaspartamide derivatives bearing alkyl ether pendants, named PASP-OCx. The chem. structures and mol. weights of the obtained polymers were characterized and confirmed by FTIR, ¹H NMR and SEC-MALLS. The water-solubilities, surface tensions and transmittances of PASP-OCx aqueous solutions were also investigated. Results showed that PASP-OCx can be dissolved in deionized water when x is less than or equal to 5. The surface tensions of PASP-OC4 and PASP-OC5 solutions exhibited obvious turning points. Interestingly, transmittances results showed that PASP-OC5 exhibited temperature responsive behaviors under acidic, neutral or alk. conditions (pH ≤ 10.0); PASP-OC4 only exhibited temperature responsive behaviors under acidic condition (pH ≤ 3.0); while PASP-OC3 did not exhibit temperature responsive behavior. The LCST value of PASP-OC5 and PASP-OC4 can be turned by adjusting the pH value of their solutions, and decreases with decreasing the pH value. Addnl., the influence of pH on the LCST values of PASP-OC4 and PASP-OC5 was investigated by zeta potential, and the results showed that the decrease of LCST values may be due to the reducing of electrostatic repulsion with pH decreasing. Therefore, results showed that pH can also affect the temperature responsive behavior of temperature-responsive polyaspartamide derivatives that do not contain hydroxyl groups. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Product Details of 109-85-3).

2-Methoxyethylamine (cas: 109-85-3) 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. 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.Product Details of 109-85-3

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

Structure-Guided Discovery of Silicon-Containing Subnanomolar Inhibitor of Hydroxyphenylpyruvate Dioxygenase as a Potential Herbicide was written by Qu, Ren-Yu;Nan, Jia-Xu;Yan, Yao-Chao;Chen, Qiong;Ndikuryayo, Ferdinand;Wei, Xue-Fang;Yang, Wen-Chao;Lin, Hong-Yan;Yang, Guang-Fu. And the article was included in Journal of Agricultural and Food Chemistry in 2021.Electric Literature of C3H9NO The following contents are mentioned in the article:

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been recognized as one of the most promising targets in the field of herbicide innovation considering the severity of weed resistance currently. In a persistent effort to develop effective HPPD-inhibiting herbicides, a structure-guided strategy was carried out to perform the structural optimization for triketone-quinazoline-2,4-diones, a novel HPPD inhibitor scaffold first discovered in our laboratory Herein, starting from the crystal structure of Arabidopsis thaliana (At)HPPD complexed with 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(o-tolyl)quinazoline-2,4(1H,3H)-dione (MBQ), three subseries of quinazoline-2,4-dione derivatives were designed and prepared by optimizing the hydrophobic interactions between the side chain of the core structure at the R¹ position and the hydrophobic pocket at the active site entrance of AtHPPD. 6-(2-Hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(3-(trimethylsilyl)prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione (I) with the best inhibitory activity against AtHPPD was identified to be the first subnanomolar-range AtHPPD inhibitor (K_i = 0.86 nM), which significantly outperformed that of the lead compound MBQ (K_i = 8.2 nM). Further determination of the crystal structure of AtHPPD in complex with compound 60 (1.85 Å) and the binding energy calculation provided a mol. basis for the understanding of its high efficiency. Addnl., the greenhouse assay indicated that 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-propylquinazoline-2,4(1H,3H)-dione (II) and compound I showed acceptable crop safety against peanut and good herbicidal activity with a broad spectrum. Moreover, compound II also showed superior selectivity for wheat at the dosage of 120 g ai/ha and favorable herbicidal efficacy toward the gramineous weeds at the dosage of as low as 30 g ai/ha. We believe that compounds II and I have promising prospects as new herbicide candidates for wheat and peanut fields. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Electric Literature 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, including apples, durians, pears, bananas, pineapples, and strawberries. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Electric Literature of C3H9NO

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

Structural effects of morpholine replacement in ZSTK474 on Class I PI3K isoform inhibition: Development of novel MEK/PI3K bifunctional inhibitors was written by Van Dort, Marcian E.;Jang, Yongsoon;Bonham, Christopher A.;Heist, Kevin;Palagama, Dilrukshika S. W.;McDonald, Lucas;Zhang, Edward Z.;Chenevert, Thomas L.;Luker, Gary D.;Ross, Brian D.. And the article was included in European Journal of Medicinal Chemistry in 2022.Computed Properties of C3H9NO The following contents are mentioned in the article:

Established roles for PI3K and MAPK signaling pathways in tumorigenesis has prompted extensive research towards the discovery of small-mol. inhibitors as cancer therapeutics. However, significant compensatory regulation exists between these two signaling cascades, leading to redundancy among survival pathways. Consequently, initial clin. trials aimed at either PI3K or MEK inhibition alone have proven ineffective and highlight the need for development of targeted and innovative therapeutic combination strategies. We designed a series of PI3K inhibitor derivatives wherein a single morpholine group of the PI3K inhibitor ZSTK474 was substituted with a variety of 2-aminoethyl functional groups. Analogs with pendant hydroxyl or methoxy groups maintained low nanomolar inhibition towards PI3Kα, PI3Kγ, and PI3Kδ isoforms in contrast to those with pendant amino groups which were significantly less inhibitory. Synthesis of prototype PI3K/MEK bifunctional inhibitors (N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide, N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide) was guided by the structure-activity data, where a MEK-targeting inhibitor was tethered directly via a short PEG linker to the triazine core of the PI3K inhibitor analogs. These compounds (N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide, N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide) displayed nanomolar inhibition towards PI3Kα, δ, and MEK (IC₅₀ ∼105-350 nM), and low micromolar inhibition for PI3Kβ and PI3Kγ (IC₅₀ ∼1.5-3.9 μM) in enzymic inhibition assays. Cell viability assays demonstrated superior anti-proliferative activity for N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide over N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide in three tumor-derived cell lines (A375, D54, SET-2), which correlated with inhibition of downstream AKT and ERK1/2 phosphorylation. Compounds N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide and N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide also demonstrated in vivo tolerability with therapeutic efficacy through reduction of kinase activation and amelioration of disease phenotypes in the JAK2V617F mutant myelofibrosis mouse cancer model. Taken together, these results support further structure optimization of N-(2-(2-(2-(2-((4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6-morpholino-1,3,5-triazin-2-yl)amino)ethoxy)ethoxy)ethoxy)ethoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide and N-((3-(4-(2-(difluoromethyl)-1H-benzo[d]imidazole-1-yl)-6morpholino-1,3,5-triazin-2-yl)-1-hydroxy-6,9,12-trioxa-3azatetradecan-14-yl)oxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide as promising leads for combination therapy in human cancer as a new class of PI3K/MEK bifunctional inhibitors. 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 typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Computed Properties of C3H9NO

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

Geometrical variations of two manganese(II) complexes with closely related quinoline-based tripodal ligands was written by Frey, Steven T.;Ballot, Jasper G.;Hands, Allison;Cirka, Haley A.;Rinaolo, Katheryn C.;Phalkun, Nich N.;Kaur, Manpreet;Jasinski, Jerry P.. And the article was included in Acta Crystallographica in 2021.Quality Control of 2-Methoxyethylamine The following contents are mentioned in the article:

Structural analyzes of the compounds di-μ-acetato-κ4O:O′;-bis{[2-methoxy-N,N-bis(quinolin-2-ylmethyl)ethanamine-κ4N,N′,N′′,O]manganese(II)} bis(tetraphenylborate) dichloromethane 1.45-solvate, [Mn₂(C₂₃O₂)₂(C₂₃H₂₃N₃O)₂](C₂₄H₂₀B).1.45CH₂Cl₂ or [Mn(DQMEA)(μ-OAc)₂Mn(DQMEA)](BPh₄)₂.1.45CH₂Cl₂ or [1](BPh₄)₂.1.45CH₂Cl₂, and (acetato-κO)[2-hydroxy-N,N-bis(quinolin-2-ylmethyl)ethanamine-κ4N,N′,N′′,O](methanol-κO)manganese(II) tetraphenylborate methanol monosolvate, [Mn(CH3COO)(C22H21N3O)(CH3OH)](C24H20B).CH3OH or [Mn(DQEA)(OAc)(CH3OH)]BPh4.CH3OH or [2]BPh4.CH3OH, by single-crystal X-ray diffraction reveal distinct differences in the geometry of coordination of the tripodal DQEA and DQMEA ligands to MnII ions. In the asym. unit, compound [1](BPh₄)₂.(CH₂Cl₂)1.45 crystallizes as a dimer in which each manganese(II) center is coordinated by the central amine nitrogen, the nitrogen atom of each quinoline group, and the methoxy-oxygen of the tetradentate DQMEA ligand, and two bridging-acetate oxygen atoms. The sym. MnII centers have a distorted, octahedral geometry in which the quinoline nitrogen atoms are trans to each other resulting in co-planarity of the quinoline rings. For each MnII center, a coordinated acetate oxygen participates in C-H…O hydrogen-bonding interactions with the two quinolyl moieties, further stabilizing the trans structure. Within the crystal, weak π-π stacking interactions and intermol. cation-anion interactions stabilize the crystal packing. In the asym. unit, compound [2]BPh₄.CH₃OH crystallizes as a monomer in which the manganese(II) ion is coordinated to the central nitrogen, the nitrogen atom of each quinoline group, and the alc. oxygen of the tetradentate DQEA ligand, an oxygen atom of OAc, and the oxygen atom of a methanol ligand. The geometry of the MnII center in [2]BPh₄.CH₃OH is also a distorted octahedron, but the quinoline nitrogen atoms are cis to each other in this structure. Hydrogen bonding between the acetate oxygen atoms and hydroxyl (O-H…O) and quinolyl (C-H…O and N-H…O) moieties of the DQEA ligand stabilize the complex in this cis configuration. Within the crystal, dimerization of complexes occurs by the formation of a pair of intermol. O₃-H₃…O₂ hydrogen bonds between the coordinated hydroxyl oxygen of the DQEA ligand of one complex and an acetate oxygen of another. Addnl. hydrogen-bonding and intermol. cation-anion interactions contribute to the crystal packing. This study involved multiple reactions and reactants, such as 2-Methoxyethylamine (cas: 109-85-3Quality Control of 2-Methoxyethylamine).

2-Methoxyethylamine (cas: 109-85-3) 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. 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.Quality Control of 2-Methoxyethylamine

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