Tag: 200-300

Structure-activity relationship investigation for imidazopyrazole-3-carboxamide derivatives as novel selective inhibitors of Bruton’s tyrosine kinase was written by Zhang, Dandan;Xu, Guiqing;Zhao, Jie;Wang, Yue;Wu, Xiaofang;He, Xing;Li, Wei;Zhang, Shuting;Yang, Shouning;Ma, Chunhua;Jiang, Yuqin;Ding, Qingjie. And the article was included in European Journal of Medicinal Chemistry in 2021.Related Products of 54916-28-8 This article mentions the following:

BTK (Bruton’s tyrosine kinase) inhibitors are the most promising drugs for the treatment of hematol. tumors. A high selectivity of BTK inhibitors ensures reduced side effects from off-targeting. Accordingly, here, based on Zanubrutinib, we designed and synthesized a new range of I, II and III. as novel BTK inhibitors that retained the amide group for improved selectivity. These compounds revealed potent inhibitory activity against BTK in vitro. Remarkably, compounds I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] (IC₅₀ 5.2 nM) and I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] (IC₅₀ 4.9 nM) possessed the highest kinase selectivity. Both of these effectively inhibited the auto-phosphorylation of BTK, blocked the cell cycle in G0/G1 phase, and induced apoptosis in the TMD8 cells. In a TMD8 cells xenograft model, a twice-daily dose of compound I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] at 25 mg/kg and a thrice-daily dose of compound I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] at 15 mg/kg significantly suppressed the tumor growth without obvious toxicity. Collectively, I [R¹ = acryloyl, R² = R³ = H; m = 1, n = 2] and I [R¹ = but-2-ynoyl, R² = R³ = H; m = 1, n = 2] are the potential selective BTK inhibitors that can be developed further. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Related Products of 54916-28-8).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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. 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.Related Products of 54916-28-8

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

FeCl₃/PPh₃-catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes was written by Sawant, Dinesh N.;Tambade, Pawan J.;Wagh, Yogesh S.;Bhanage, Bhalchandra M.. And the article was included in Tetrahedron Letters in 2010.SDS of cas: 75581-11-2 This article mentions the following:

Conditions for a FeCl₃/PPh₃-catalyzed and palladium-, copper-, amine free-Sonogashira coupling reaction of aryl halides with terminal alkynes are reported. The protocol was applicable to a wide variety of substituted aryl iodides and alkynes with different steric and electronic properties and gave excellent yields of the desired coupling products. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2SDS of cas: 75581-11-2).

4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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. 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).SDS of cas: 75581-11-2

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

C-5-Disubstituted Barbiturates as Potential Molecular Probes for Noninvasive Matrix Metalloproteinase Imaging was written by Breyholz, Hans-Joerg;Schaefers, Michael;Wagner, Stefan;Hoeltke, Carsten;Faust, Andreas;Rabeneck, Helmut;Levkau, Bodo;Schober, Otmar;Kopka, Klaus. And the article was included in Journal of Medicinal Chemistry in 2005.Application In Synthesis of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone This article mentions the following:

Studies have demonstrated a pos. correlation between inflammation, metastasis, or atherosclerosis and the unbalanced or culminated expression of matrix metalloproteinases (MMPs). The mol. imaging of locally upregulated MMP activity in vivo is a clin. challenge. Actually, radioligands based on nonpeptidyl MMP inhibitors (MMPIs) are currently in development as putative radiopharmaceutical agents for the noninvasive in vivo assessment of activated MMPs. Nonpeptidyl MMPIs bind to the zinc active site of the activated enzyme via mono- (e.g. carboxylate) or bidentate (e.g. hydroxamate) complexation thereby exhibiting a broad-spectrum MMP binding potency. Thus, these mentioned endopeptidase inhibitors should be useable lead compounds for the redevelopment as diagnostic MMPI radiotracers. Recently, the non-hydroxamate C-5-disubstituted pyrimidine-2,4,6-triones were disclosed as subgroup-selective MMP inhibitors. We here describe a set of fine-tuned barbiturates as a new class of MMPI radiotracers for the noninvasive in vivo visualization of activated MMPs using scintigraphic techniques such as SPECT or PET. In the experiment, the researchers used many compounds, for example, 1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8Application In Synthesis of 1-(4-(4-Methoxyphenoxy)phenyl)ethanone).

1-(4-(4-Methoxyphenoxy)phenyl)ethanone (cas: 54916-28-8) 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 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-(4-(4-Methoxyphenoxy)phenyl)ethanone

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

Ab initio and density functional theoretical design and screening of model crown ether based ligand (host) for extraction of lithium metal ion (guest): effect of donor and electronic induction was written by Boda, Anil;Ali, Sk. Musharaf;Rao, Hanmanth;Ghosh, Sandip K.. And the article was included in Journal of Molecular Modeling in 2012.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane This article mentions the following:

The structures, energetic and thermodn. parameters of model crown ethers with different donor, cavity and electron donating/ withdrawing functional group were determined with ab initio MP2 and d. functional theory in gas and solvent phase. The calculated values of binding energy/enthalpy for lithium ion complexation are marginally higher for hard donor based aza and oxa crown compared to soft donor based thia and phospha crown. The calculated values of binding enthalpy for lithium metal ion with 12C4 at MP2 level of theory is in good agreement with the available exptl. result. The binding energy is altered due to the inductive effect imparted by the electron donating/ withdrawing group in crown ether, which is well correlated with the values of electron transfer. The role of entropy for extraction of hydrated lithium ion by different donor and functional group based ligand was demonstrated. The HOMO-LUMO gap is decreased and dipole moment of the ligand is increased from gas phase to organic phase because of the dielec. constant of the solvent. The gas phase binding energy is reduced in solvent phase as the solvent mols. weaken the metal-ligand binding. The theor. values of extraction energy for LiCl salt from aqueous solution in different organic solvent is validated by the exptl. trend. The study presented here should contribute to the design of model host ligand and screening of solvent for metal ion recognition and thus can contribute in planning the experiments In the experiment, the researchers used many compounds, for example, 1,4,7,10-Tetraoxa-13-azacyclopentadecane (cas: 66943-05-3Application In Synthesis 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. 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.Application In Synthesis of 1,4,7,10-Tetraoxa-13-azacyclopentadecane

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

Synthesis and bioactivity of erythromycin derivatives was written by Chen, Mingwei;Muri, Estela M. F.;Jacob, Melissa;Williamson, John S.. And the article was included in Medicinal Chemistry Research in 2003.Recommanded Product: 1,1-Diisopropoxycyclohexane This article mentions the following:

A small series of semisynthetic 6-O-alkylated erythromycin derivatives were synthesized and evaluated for their antimicrobial activity. A dichlorobenzenyl 6-O-allyl erythromycin derivative (I) was found to be active against Cryptococcus neoformans (IC₅₀ 5.0 μg/mL), Staphylococcus aureus (IC₅₀ 5.0 μg/mL), and methicillin-resistant S. aureus (IC₅₀ 5.0 μg/mL). In the experiment, the researchers used many compounds, for example, 1,1-Diisopropoxycyclohexane (cas: 1132-95-2Recommanded Product: 1,1-Diisopropoxycyclohexane).

1,1-Diisopropoxycyclohexane (cas: 1132-95-2) 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. 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.Recommanded Product: 1,1-Diisopropoxycyclohexane

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

Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation. Preparation of α,β-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands was written by Rossi, D.;Urbano, M.;Baraglia, A. Carnevale;Serra, M.;Bergamelli, F.;Iannelli, M.;Azzolina, O.;Collina, S.. And the article was included in Synthetic Communications in 2009.Recommanded Product: 6972-61-8 This article mentions the following:

The optimal conditions to prepare α,β-unsaturated Me esters via Wittig reaction combining polymer-assisted solution-phase synthesis (PASPS) methodol. and simultaneous ultrasound and microwave irradiation were established. The effects of temperature, solvent, and irradiation time were discussed. Results clearly indicated the superiority of combined ultrasound and microwave-assisted procedure over microwave-assisted methodol. Moreover, an efficient PASPS procedure to prepare α,β-unsaturated carboxylic acids via tandem Wittig olefination and hydrolysis reaction was developed under combined ultrasound and microwave irradiation Generally, a good conversion of aldehydes to acids was observed The optimized protocols allowed us to quickly prepare a small collection of either α,β-unsaturated esters or carboxylic acids, key intermediates for the drug-discovery process of new sigma ligands. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Recommanded Product: 6972-61-8).

3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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―H or N―H 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.Recommanded Product: 6972-61-8

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

Amidines in the Diels-Alder synthesis was written by Martinez, Joaquin Royo. And the article was included in Rev. real. acad. cienc. exact. fís. y nat. Madrid in 1952.SDS of cas: 51488-33-6 This article mentions the following:

Several amidines were prepared as follows. CH₂(OH)CH₂Cl + NaCN → CH₂(OH)CH₂CN (I), b₁₅ 110° (84%); I + finely divided Al (hydroquinone to eliminate polymerization) → CH₂:CHCN (II), b. 77.6-79.0° (69.3%); II + EtOH (distilled from Na), saturated with gaseous HCl → CH₂:CHC(:NH₂Cl)OEt (III), m. 104-4.5° (decomposition), stable in bottles with airtight stoppers; III in absolute EtOH + NH₃ in absolute EtOH (3 hr. agitation, followed by standing 2 days) → CH₂:CHC(:NH₂Cl)NH₂. Similarly, vanillin + NaOH + MeI → (MeO)₂C₆H₃CHO → (MeO)₂C₆H₃CH:NOH → (MeO)₂C₆H₃CN, m. 67°, → (MeO)₂C₆H₃C(:NH₂Cl)OEt, m. 141° (decomposition) → (MeO)₂C₆H₃C(:NH₂Cl)NH₂, m. 237°. Piperonal → oxime, m. 110°, → piperonylonitrile, m. 94.5°, → Et piperonylimidate-HCl, m. 122-3°, → piperonylamidine-HCl, m. 238° (decomposition) → piperonylamidine, m. 167°, → picrate, m. 257°. PhCN → m-O₂NC₆H₄CN, m. 117.5°, → m-O₂NC₆H₄C(:NH₂Cl)OEt → m-O₂NC₆H₄(:NH₂Cl)NH₂, m. 250° (decomposition). There was no reaction comparable to a Diels-Alder, between these amidines and styrene, anethole, or maleic anhydride. MeNO₂ and CH₂(OH)CN, used as solvents, were prepared by the decarboxylation of CH₂(NO₂)CO₂H and by the addition of HCN to CH₂O, resp. In the experiment, the researchers used many compounds, for example, 3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6SDS of cas: 51488-33-6).

3,4-Dimethoxybenzimidamide hydrochloride (cas: 51488-33-6) 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. 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.SDS of cas: 51488-33-6

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

Synthesis of analogs of the Gwt1 inhibitor manogepix (APX001A) and in vitro evaluation against Cryptococcus spp was written by Trzoss, Michael;Covel, Jonathan A.;Kapoor, Mili;Moloney, Molly K.;Soltow, Quinlyn A.;Webb, Peter J.;Shaw, Karen Joy. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Formula: C14H15BO4 This article mentions the following:

Fosmanogepix (APX001) is a first-in-class prodrug mol. that is currently in Phase 2 clin. trials for invasive fungal infections. The active moiety manogepix (APX001A) inhibits the novel fungal protein Gwt1. Gwt1 catalyzes an early step in the GPI anchor biosynthesis pathway. Here we describe the synthesis and evaluation of 292 new and 24 previously described analogs that were synthesized using a series of advanced intermediates to allow for rapid analoging. Several compounds demonstrated significantly (8- to 32-fold) improved antifungal activity against both Cryptococcus neoformans and C. gattii as compared to manogepix. Further in vitro characterization identified three analogs with a similar preliminary safety and in vitro profile to manogepix and superior activity against Cryptococcus spp. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Formula: C14H15BO4).

(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) 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.Formula: C14H15BO4

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

New methods for calculating the temperatures and the enthalpy changes of virtual transitions and predicting phase diagrams – applied to the tolans was written by Domon, M.;Buisine, J. M.. And the article was included in Molecular Crystals and Liquid Crystals in 1987.Reference of 39969-26-1 This article mentions the following:

For a mesogen which does not exhibit an enantiotropic nematic phase when pure, 2 methods are proposed for the determination of the temperatures and enthalpy changes of the nematic-isotropic liquid virtual transitions. These calculations, based on Schroeder-van Laar and van Laar equations, use the value of the liquid appearance temperature for mixtures of the compound with another mesogen which exhibits the enantiotropic mesophase when pure. Both methods are applied to the study of the 1st 10 compounds in the 4-methoxy-4′-alkyltolan series. The results are used to determine the eutectic, liquid appearance and nematic disappearance temperatures of mixtures of 2 tolans that do not exhibit an enantiotropic nematic phase when pure. In 7 cases, an enantiotropic nematic phase is predicted and observed; in 1 case, the phase diagram differs from that expected; for the remainder, the calculated and exptl. data agree. In the experiment, the researchers used many compounds, for example, 1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1Reference of 39969-26-1).

1-Methoxy-4-((4-propylphenyl)ethynyl)benzene (cas: 39969-26-1) 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. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Reference of 39969-26-1

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

Room Temperature C-H Activation and Cross-Coupling of Aryl Ureas in Water was written by Nishikata, Takashi;Abela, Alexander R.;Lipshutz, Bruce H.. And the article was included in Angewandte Chemie, International Edition in 2010.Safety of N-(3-Methoxyphenyl)pivalamide This article mentions the following:

The first room temperature mono-C-H activation of urea derivatives and their cross-coupling with aryl iodides in water is described. This methodol. provides a convenient route to various aniline derivatives by means of C-H activation under mild conditions. In the experiment, the researchers used many compounds, for example, N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3Safety of N-(3-Methoxyphenyl)pivalamide).

N-(3-Methoxyphenyl)pivalamide (cas: 56619-93-3) 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. But on the other hand, ethers undergo cleavage by reaction with acids. 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).Safety of N-(3-Methoxyphenyl)pivalamide

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