Month: December 2022

Huang, Ying published the artcileDiscovery of the Clinical Candidate MAK683: An EED-Directed, Allosteric, and Selective PRC2 Inhibitor for the Treatment of Advanced Malignancies, Application In Synthesis of 6850-57-3, the publication is Journal of Medicinal Chemistry (2022), 65(7), 5317-5333, database is CAplus and MEDLINE.

Polycomb Repressive Complex 2 (PRC2) plays an important role in transcriptional regulation during animal development and in cell differentiation, and alteration of PRC2 activity has been associated with cancer. On a mol. level, PRC2 catalyzes methylation of histone H3 lysine 27 (H3K27), resulting in mono-, di-, or trimethylated forms of H3K27, of which the trimethylated form H3K27me3 leads to transcriptional repression of polycomb target genes. Previously, we have shown that binding of the low-mol.-weight compound EED226 to the H3K27me3 binding pocket of the regulatory subunit EED can effectively inhibit PRC2 activity in cells and reduce tumor growth in mouse xenograft models. Here, we report the stepwise optimization of the tool compound EED226 toward the potent and selective EED inhibitor MAK683 (compound 22) and its subsequent preclin. characterization. Based on a balanced PK/PD profile, efficacy, and mitigated risk of forming reactive metabolites, MAK683 has been selected for clin. development.

Journal of Medicinal Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Application In Synthesis of 6850-57-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zhang, Jinhong published the artcileStudy on the Staged and Direct Fast Pyrolysis Behavior of Waste Pine Sawdust Using High Heating Rate TG-FTIR and Py-GC/MS, Application In Synthesis of 91-16-7, the publication is ACS Omega (2022), 7(5), 4245-4256, database is CAplus and MEDLINE.

To understand the fast pyrolysis kinetics and product evolution of waste pine sawdust, high heating rate thermogravimetry-Fourier transform IR (TG-FTIR) was used to obtain the kinetic parameters and the chem. groups formed during the pyrolysis process, while pyrolysis-gas chromatog./mass spectrometry (Py-GC/MS) was used to investigate the detailed compositions of products under the staged (seven stages from 300 to 600°C) and direct fast pyrolysis process. Spectral bands were identified for acids, alcs., aldehydes, aromatics, esters, ethers, hydrocarbons, ketones, phenols, and sugars. Research found that the apparent activation energy for fast pyrolysis is much higher than that of slow pyrolysis. The evolution of CO₂ is the major deoxygenation route. Cracking mainly occurred at the 450°C stage with phenols, ketones, aldehydes, and sugars as the main products. The product distributions for different stages are significantly different; the selectivity of aldehydes decreased, while phenols showed an upward trend with an increase in pyrolysis temperature Ketones and sugars reached their peak values at 450°C. The changes in the mol. composition of each stage helped to understand the pyrolysis process. Compared with the staged pyrolysis, the direct pyrolysis process had higher selectivity of acids, aldehydes, esters, and sugars and lower selectivity of phenols, ketones, and alcs.

ACS Omega published new progress about 91-16-7. 91-16-7 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether,Inhibitor,Inhibitor,Inhibitor, name is 1,2-Dimethoxybenzene, and the molecular formula is C13H26N2, Application In Synthesis of 91-16-7.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Naidu, Ajay B. published the artcileAn efficient intermolecular BINAM-copper(I) catalyzed Ullmann-type coupling of aryl iodides/bromides with aliphatic alcohols, Name: 1-((2-Ethylhexyl)oxy)-4-methoxybenzene, the publication is Tetrahedron Letters (2008), 49(19), 3147-3151, database is CAplus.

A wide range of alkyl aryl ethers are synthesized from the corresponding aryl iodides and aliphatic alcs. through Ullmann-type intermol. coupling reactions in the presence of a catalytic amount of easily available BINAM-CuI complex. Less reactive aryl bromides also reacted with aliphatic alcs. under identical conditions to give good yields of the alkyl aryl ethers without increasing the reaction temperature and time.

Tetrahedron Letters published new progress about 146370-51-6. 146370-51-6 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 1-((2-Ethylhexyl)oxy)-4-methoxybenzene, and the molecular formula is C15H24O2, Name: 1-((2-Ethylhexyl)oxy)-4-methoxybenzene.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileB-[(E)-3-(Diphenylamino)allyl]diisopinocampheylborane: an excellent reagent for the stereoselective synthesis of anti-β-diphenylamino alcohols, Category: ethers-buliding-blocks, the publication is Journal of the Chemical Society, Chemical Communications (1993), 339-41, database is CAplus.

Anti-β-Amino alcs. have been produced with high relative and absolute stereochem. control in a simple one-pot process via the reaction of aldehydes with B-[(E)-3-(diphenylamino)allyl]diisopinocampheylborane and alk. hydrogen peroxide work-up.

Journal of the Chemical Society, Chemical Communications published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileThe use of B-[(E)-3-(diphenylamino)allyl]diisopinocampheylborane as a reagent for the stereoselective synthesis of anti-β-diphenylamino alcohols and trans-1-diphenylamino-2-(1-hydroxylalkyl)cyclopropanes, Formula: C21H37BO, the publication is Tetrahedron (1993), 49(36), 7857-70, database is CAplus.

Anti-β-Amino alcs., e.g. (3R,4S)-4-(diphenylamino)-1,5-hexadien-3-ol (I), and trans-1-amino-2-(1-hydroxyalkyl)cyclopropanes, e.g. II, were prepared with high relative and absolute stereocontrol in a simple one-pot process via the reaction of aldehydes with B-[(E)-3-(diphenyamino)allyl]-diisopinocampheylborane and a subsequent alk. hydrogen peroxide work-up. The crystal structures of Mosher ester of I and cyclopropane II were determined

Tetrahedron published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Burmaoglu, Serdar published the artcileSyntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents, Product Details of C10H14O, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2017), 32(1), 878-884, database is CAplus and MEDLINE.

Four multicaulin and miltirone-like phenanthrene derivatives were synthesized and evaluated as antituberculosis agents. The crucial step of the synthesis was Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene. 2-Isopropyl-3-methoxy-9,10-dihydrophenanthrene was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions. The best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol.

Journal of Enzyme Inhibition and Medicinal Chemistry published new progress about 2944-47-0. 2944-47-0 belongs to ethers-buliding-blocks, auxiliary class Benzene,Ether, name is 2-Isopropylanisole, and the molecular formula is C10H14O, Product Details of C10H14O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Nau, Heinz published the artcileWeak acids may act as teratogens by accumulating in the basic milieu of the early mammalian embryo, Quality Control of 16332-06-2, the publication is Nature (London, United Kingdom) (1986), 323(6085), 276-8, database is CAplus and MEDLINE.

Among the 11 drugs or chems. which are well-documented human teratogens, 8 (or their main metabolites) are weak acids whereas none is a weak base. Moreover, 23 out of 32 acids tested were teratogenic in at least 1 animal species. The acidic property of drugs may therefore be an important determinant of teratogenicity. The intracellular pH (pH_i) of the mouse and rat embryo is higher than that of maternal plasma, as determined by the relative accumulation of dimethadione  [695-53-4]. The antiepileptic drug valproic acid  [99-66-1] and its pharmacol. active unsaturated metabolite accumulate in embryonic tissue to higher concentrations than in maternal plasma, whereas the essentially neutral amide of valproic acid (valpromide  [2430-27-5]) or ethosuximide  [77-67-8] do not accumulate in the embryo; in the rat the pH_i of the embryo decreases with advancing gestation; in general agreement with the pH partiton hypothesis, the exposure of the embryo to valproic acid also decreases significantly during that period. Furthermore, the amides of 2 weak acid teratogens, valpromide and methoxyacetamide  [16332-06-2], and ethosuximide, are much less teratogenic than their acid counterparts. Thus, weakly acidic drugs, by virtue of their physicochem. nature, accumulate in the early embryo with its relatively high pH_i.

Nature (London, United Kingdom) published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Quality Control of 16332-06-2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Tuesley, Sidney P. published the artcileDevelopment and evaluation of a sampling device for the analysis of pharmaceutical aerosols, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, the publication is Journal of Pharmaceutical Sciences (1968), 57(3), 488-93, database is CAplus and MEDLINE.

Various devices and techniques were studied in an attempt to obtain suitable samples of material from aerosol products. Generally accepted sampling procedures cannot be used since the aerosol product contains propellants that are extremely volatile. Several of these methods were investigated and used as the basis for assaying various aerosol products. A sampling device was developed and evaluated. The sampling device was designed in a manner that made available a sample of aerosol product that could then be assayed directly in the chamber. Openings were fitted with specially designed valves that allow for transfer of the contents without loss of volatile propellant or active ingredients. Various samples of aerosol products containing local anesthetics, steroids, and amines, were assayed by this method and gave acceptable results. In all cases, the amount of active ingredient contained in each product could be accurately determined The device makes possible a technique applicable to the anal. of most pharmaceutical aerosols. This method, which can be carried out with ease in a relatively short period of time, produced accurate results when used in the manner described.

Journal of Pharmaceutical Sciences published new progress about 637-58-1. 637-58-1 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride, and the molecular formula is C19H14Cl2, Safety of 4-(3-(4-Butoxyphenoxy)propyl)morpholine hydrochloride.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Busch, M. published the artcileReactions of diazonium salts with thioureas and derivatives, Related Products of ethers-buliding-blocks, the publication is Journal fuer Praktische Chemie (Leipzig) (1938), 173-85, database is CAplus.

cf. Ber. 34, 320(1901). PhNHNHCSNHPh (I) in Me₂CO at -5°, treated with PhN₂Cl in Me₂CO, gives a vigorous evolution of N₂, with the formation of the HCl salt, decomposes 205°, of S-phenyl-1,4-diphenylthiosemicarbazide (II), PhNHNHC(SPh):NPh, m. 75°. II is easily degraded by alkali into I and PhSH. The mother liquor from II yields benzeneazophenyliminomethane thiophenyl ether (III), PhN:NC(SPh):NPh, red, m. 115°; this is the oxidation product of II and is formed from II with H₂O₂ or yellow HgO; III gives II with (NH₄)₂S. The p-nitrophenyl homolog of II forms a HCl salt (IV), pale yellow, decomposes 205°; the free base is so susceptible to hydrolysis that NH₄OH in EtOH gives (p-O₂NC₆H₄S)₂. With HCHO IV yields the diphenyldihydrotriazole ether of p-nitrothiophenol, PhN.N:C(SC₆H₄NO₂).NPh.CH₂, m. 127°; BzH gives the tri-Ph homolog, PhN.N:C(SC₆H₄NO₂).NPh.CHPh, brownish rose, m. 124°. The red azo compound m. 118°. (PhNH)₂CS and p-O₂NC₆H₄N₂Cl (V) in EtOH-Me₂CO at -5° give S-p-nitrophenyldiphenylisothiourea (VI), PhNHC(SC₆H₄NO₂):NPh, light yellow, m. 131°; on recrystallization from EtOH partial decomposition occurs into (PhNH)₂CO and p-O₂NC₆H₄SH; alkali gives complete hydrolysis. The p-Br derivative of VI, p-BrC₆H₄NH(CSC₆H₄NO₂):NPh, light yellow, m. 158°, results in 75% yield from p-BrC₆H₄NHCSHPh. CS(NH₂)₂ and PhN₂Cl in Me₂CO give [H₂NC(:NH)S]₂.2HCl, m. 173-4° (decomposition). V gives 84% of the compound H₂NC(:NH)SN:NC₆H₄NO₂ as the HCl salt; this salt decomposes in absolute EtOH at room temperature PhNHCO₂Et and V in Me₂CO at -5° give the p-nitrophenyl ether of p-nitrobenzenediazohydrosulfide (VII), O₂NC₆H₄N:NSC₆H₄NO₂, citron-yellow, decomposes 142°; it results in varying amounts by coupling different thiourethans with V. PhN:C(SH)OCH₂Ph and V in EtOH-Me₂CO give VII; in C₆H₆ there results the compound PhNHCOSC₆H₄NO₂, m. 158°.

Journal fuer Praktische Chemie (Leipzig) published new progress about 14807-75-1. 14807-75-1 belongs to ethers-buliding-blocks, auxiliary class Salt,Thiourea,Amine,Aliphatic hydrocarbon chain, name is Formamidine disulfide dihydrochloride, and the molecular formula is C2H8Cl2N4S2, Related Products of ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Dahiya, Amit published the artcileBase-Mediated Direct C-H Germylation of Heteroarenes and Arenes, Synthetic Route of 93-04-9, the publication is Organic Letters (2021), 23(15), 6010-6013, database is CAplus and MEDLINE.

The direct C-H germylation of heteroarenes, arenes, and benzylic C-H bonds promoted by lithium tetramethylpiperidide (LiTMP) is reported. The method is rapid, selective, and operationally simple, consisting of direct addition of all reagents at room temperature (one-pot procedure). The synthetic utility of these newly accessed aryl germanes as viable coupling partners in Pd catalysis is also showcased.

Organic Letters published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Synthetic Route of 93-04-9.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem