Month: December 2022

Gargano, Emanuele M. published the artcileMetabolic stability optimization and metabolite identification of 2,5-thiophene amide 17β-hydroxysteroid dehydrogenase type 2 inhibitors, Name: (3-Methoxy-5-methylphenyl)boronic acid, the publication is European Journal of Medicinal Chemistry (2014), 203-219, database is CAplus and MEDLINE.

17β-HSD2 is a promising new target for the treatment of osteoporosis. In this paper, a rational strategy to overcome the metabolic liability in the 2,5-thiophene amide class of 17β-HSD2 inhibitors is described, and the biol. activity of the new inhibitors. Applying different strategies, as lowering the cLogP or modifying the structures of the mols., three compounds with strongly improved metabolic stability were obtained. For understanding biotransformation in the 2,5-thiophene amide class the main metabolic pathways of three properly selected compounds were elucidated.

European Journal of Medicinal Chemistry published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C8H11BO3, Name: (3-Methoxy-5-methylphenyl)boronic acid.

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

Becerra-Martinez, Elvia published the artcileEquilibrating magnetic dispersion and magnet homogeneity for the high-resolution proton nuclear magnetic resonance of monosubstituted naphthalenes, Application In Synthesis of 93-04-9, the publication is Spectroscopy Letters (2022), 55(6), 424-436, database is CAplus.

Accurate chem. shift and coupling constant for 1- and 2-naphthyl derivatives were decipher by iterative full spin anal. Each of the seven magnetically nonequivalent H2-H8 atoms in 1-naphthyl derivatives, or of the H1, H3-H8 atoms in 2-naphthyl derivatives were unambiguously identified by analyzing their intra- and inter-ring coupling constants at 300 MHz and by two-dimensional homo- and heteronuclear experiments at 750 MHz. ¹³C chem. shifts were also determined during this study, from where some literature ambiguities were resolved using long-range C-H correlations at 750 MHz. The complete proton NMR parameters are herein ascribed for the first time.

Spectroscopy 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, Application In Synthesis of 93-04-9.

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

McDonald, Frank E. published the artcileStereo- and regioselective synthesis of 2-amino-3,5-diols via stereospecific crotyl transfer and regioselective aminohydroxylation, SDS of cas: 99438-28-5, the publication is Synthesis (2012), 44(23), 3639-3648, database is CAplus.

A short synthesis of 2-amino-3,5-diols is described, including the all-S isomer enigmol, a synthetic anticancer compound inspired by the structure of fumonisin B₁. The synthetic route features stereospecific crotyl transfer to tetradecanal via pericyclic oxonia-Cope rearrangement; stereoselective epoxidation of the alkene; regioselective epoxide opening with azide; and reduction of azide to amine. This manuscript also corrects a structure assignment error in a previously reported synthesis of one of the diastereomers of enigmol.

Synthesis 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, SDS of cas: 99438-28-5.

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

Ma, Lijuan published the artcileEffect of main taste compounds on the release of methoxyphenolic compounds in Pu-erh tea, Category: ethers-buliding-blocks, the publication is LWT–Food Science and Technology (2022), 113293, database is CAplus.

As a typical Chinese tea, Pu-erh tea attracts much attention due to its unique flavor formed by taste and aroma compounds To study the effects of taste compounds on the aroma release, model solutions containing five typical methoxyphenolic compounds (MCs) and main taste compounds with different concentrations were prepared based on the anal. of Pu-erh tea samples. GC-MS results indicated that the release of five MCs was inhibited by theabrownin, tea polysaccharide, tea polyphenol and catechins. The release of 1,2-dimethoxybenzene, 3,4-dimethoxytoluene and 1,2,3-trimethoxy-5-methyl-benzene was promoted by gallic acid under a low concentration (≤4 mg/g). Statistically, gallic acid had the most significant effect on the release of MCs. Isothermal titration calorimetry suggested that hydrogen bonds and hydrophobic effects had potential contributions to the interaction between taste and aroma compounds This work will provide the research basis for revealing the formation mechanism of tea flavor.

LWT–Food Science and Technology 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 C8H10O2, Category: ethers-buliding-blocks.

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

Yang, Mingze published the artcileTotal Synthesis of Dysoxylactam A, SDS of cas: 99438-28-5, the publication is Organic Letters (2020), 22(5), 1776-1779, database is CAplus and MEDLINE.

The total synthesis of a potent multi-drug-resistant reverser, dysoxylacatam A (1), was achieved in a highly efficient and stereocontrolled fashion. The highlights of the strategy enlisted an iterative combination of lithiation-borylation tactics including Aggarwal homologation and Matteson homologation, Brown crotylation, Krische allylation, and ring-closing metathesis to forge the macrocycle.

Organic Letters 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 C8H10O2, SDS of cas: 99438-28-5.

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

Deng, Yuqing published the artcileSelection of DNA-Encoded Dynamic Chemical Libraries for Direct Inhibitor Discovery, Synthetic Route of 77128-73-5, the publication is Angewandte Chemie, International Edition (2020), 59(35), 14965-14972, database is CAplus and MEDLINE.

Dynamic combinatorial libraries (DCLs) is a powerful tool for ligand discovery in biomedical research; however, the application of DCLs has been hampered by their low diversity. Recently, the concept of DNA encoding has been employed in DCLs to create DNA-encoded dynamic libraries (DEDLs); however, all current DEDLs are limited to fragment identification, and a challenging process of fragment linking is required after selection. The authors report an anchor-directed DEDL approach that can identify full ligand structures from large-scale DEDLs. This method is also able to convert unbiased libraries into focused ones targeting specific protein classes. The authors demonstrated this method by selecting DEDLs against five proteins, and novel inhibitors were identified for all targets. Notably, several selective BD1/BD2 inhibitors were identified from the selections against bromodomain 4 (BRD4), an important anti-cancer drug target. This work may provide a broadly applicable method for inhibitor discovery.

Angewandte Chemie, International Edition published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Synthetic Route of 77128-73-5.

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

Sarnowski, Matthew P. published the artcileSynthesis and β-sheet propensity of constrained N-amino peptides, Computed Properties of 77128-73-5, the publication is Bioorganic & Medicinal Chemistry (2018), 26(6), 1162-1166, database is CAplus and MEDLINE.

The stabilization of β-sheet secondary structure through peptide backbone modification represents an attractive approach to protein mimicry. Here, we present strategies toward stable β-hairpin folds based on peptide strand N-amination. Novel pyrazolidinone and tetrahydropyridazinone dipeptide constraints were introduced via on-resin Mitsunobu cyclization between α-hydrazino acid residues and a serine or homoserine side chain. Acyclic and cyclic N-amino peptide building blocks were then evaluated for their effect on β-hairpin stability in water using a GB1-derived model system. Our results demonstrate the strong β-sheet stabilizing effect of the peptide N-amino substituent, and provide useful insights into the impact of covalent dipeptide constraint on β-sheet folding.

Bioorganic & Medicinal Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Computed Properties of 77128-73-5.

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

Roodbeen, Renee published the artcileMicrowave Heating in the Solid-Phase Synthesis of N-Methylated Peptides: When Is Room Temperature Better?, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, the publication is European Journal of Organic Chemistry (2012), 2012(36), 7106-7111, database is CAplus.

The N-methylation of backbone amides in synthetic peptides is an important method for improving properties such as bioavailability, stability, as well as structural preferences, and is thus an attractive design strategy. However, the synthesis of N-methylated peptides can be challenging as the nucleophile in the acylation step is a sterically hindered secondary amine. In this study, the authors have systematically evaluated the use of microwave heating, different coupling conditions and the role of steric effects on coupling yields. First, the coupling reagent providing the highest yields was identified by a series of test N-acylation reactions on a selected peptide sequence. Secondly, a comparison of the coupling temperature, i.e., room temperature vs. microwave heating, with the optimal coupling reagent was performed. Finally, under the optimal conditions, a comprehensive study employing a set of sterically hindered N-methylated amino acids was conducted. Interestingly, incorporation of Fmoc-Arg(Pbf)-OH proceeded with higher yields at room temperature than at elevated temperature as a result of intramol. Arg lactam formation, which competes with intermol. amide bond formation. Fmoc-Arg(Boc)₂-OH provided even lower coupling yields, due to the complete formation of the Arg lactam product. These studies have led to a robust, rapid, easy and high-yielding microwave-assisted method using COMU for the incorporation of Fmoc amino acids into challenging, sterically hindered N-methylated amino acid residues in a peptide sequence without the use of harsh reagents.

European Journal of Organic Chemistry published new progress about 77128-73-5. 77128-73-5 belongs to ethers-buliding-blocks, auxiliary class Inhibitor, name is (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid, and the molecular formula is C25H23NO4, Name: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acid.

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

Penland, Marine published the artcileBrine salt concentration reduction and inoculation with autochthonous consortia: Impact on Protected Designation of Origin Nyons black table olive fermentations, Related Products of ethers-buliding-blocks, the publication is Food Research International (2022), 111069, database is CAplus and MEDLINE.

Nyons table olives, named after the French city where they are processed, are naturally fermented black table olives. Their specificity relies on the use of the ‘Tanche’ olive variety harvested at full maturity and their slow spontaneous fermentation in 10% salt brine driven by yeast populations. This study aimed at investigating the benefit of inoculating autochthonous consortia to produce Nyons table olives by fermentation in 10% salt brine and in reduced salt conditions (8%). Two strategies were evaluated: inoculation with a defined autochthonous consortium and inoculation by spent brine backslopping. To define the consortium, yeasts were selected among 48 autochthonous isolates and key features included high halotolerance, low pectinolytic and proteolytic activities, however none had β-glucosidase activities. The consortium included eight yeast strains with distinct technol. properties belonging to five dominant species, i.e. Citeromyces nyonsensis, Pichia membranifaciens, Wickerhamomyces anomalus, Zygotorulaspora mrakii and Candida atlantica. Fermentation trials were conducted over a year and compared by evaluating microbial community shifts (16S and ITS metagenetics) and volatile profiles (GC-MS). Regarding fermentations with the defined consortium, four out of five species implanted in early stages while one, Pichia membranifaciens, persisted and largely dominated by the end of the fermentation Altogether, inoculation with the defined consortium did not disrupt microbial shifts compared to traditional fermentations although minor differences were observed in volatile profiles. The backslopping method yielded the highest impact on microbial populations and olive volatile profiles, with higher ester abundances at the end of fermentation Finally, reduced salt in brine gave very promising results as no deleterious effects on microbial communities, volatile dynamics but also safety criteria of the olives were observed compared to traditional fermented olives.

Food Research International 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 C8H10O2, Related Products of ethers-buliding-blocks.

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

Basak, Shubhajit published the artcilePalladium-Catalyzed 2-fold C-H Activation/C-C Coupling for C4-Arylation of Indoles Using Weak Chelation, Application In Synthesis of 91-16-7, the publication is Organic Letters (2022), 24(2), 554-558, database is CAplus and MEDLINE.

Palladium-catalyzed weak chelation-assisted regioselective C4-arylation of indoles was accomplished using a readily available arene at moderate temperature The C4-arylation, weak chelating benzoyl (Bz) directing group, cross-dehydrogenative coupling (CDC), broad substrate scope, and late-stage diversifications were the important practical features.

Organic Letters 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 C8H10O2, Application In Synthesis of 91-16-7.

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