Month: November 2022

Vily-Petit, Justine published the artcileIntestinal gluconeogenesis shapes gut microbiota, fecal and urine metabolome in mice with gastric bypass surgery, Computed Properties of 63-68-3, the publication is Scientific Reports (2022), 12(1), 1415, database is CAplus and MEDLINE.

Intestinal gluconeogenesis (IGN), gastric bypass (GBP) and gut microbiota pos. regulate glucose homeostasis and diet-induced dysmetabolism. GBP modulates gut microbiota, whether IGN could shape it has not been investigated. We studied gut microbiota and microbiome in wild type and IGN-deficient mice, undergoing GBP or not, and fed on either a normal chow (NC) or a high-fat/high-sucrose (HFHS) diet. We also studied fecal and urine metabolome in NC-fed mice. IGN and GBP had a different effect on the gut microbiota of mice fed with NC and HFHS diet. IGN inactivation increased abundance of Deltaproteobacteria on NC and of Proteobacteria such as Helicobacter on HFHS diet. GBP increased abundance of Firmicutes and Proteobacteria on NC-fed WT mice and of Firmicutes, Bacteroidetes and Proteobacteria on HFHS-fed WT mice. The combined effect of IGN inactivation and GBP increased abundance of Actinobacteria on NC and the abundance of Enterococcaceae and Enterobacteriaceae on HFHS diet. A reduction was observed in the amounf of short-chain fatty acids in fecal (by GBP) and in both fecal and urine (by IGN inactivation) metabolome. IGN and GBP, sep. or combined, shape gut microbiota and microbiome on NC- and HFHS-fed mice, and modify fecal and urine metabolome.

Scientific Reports published new progress about 63-68-3. 63-68-3 belongs to catalysis-chemistry, auxiliary class Natural product, name is (S)-2-Amino-4-(methylthio)butanoic acid, and the molecular formula is C9H9BrO2, Computed Properties of 63-68-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Romagnoli, Romeo published the artcileDesign, synthesis and biological evaluation of arylcinnamide hybrid derivatives as novel anticancer agents, Recommanded Product: (E)-3-(3-Nitrophenyl)acrylic acid, the publication is European Journal of Medicinal Chemistry (2014), 394-407, database is CAplus and MEDLINE.

The combination of two pharmacophores into a single mol. represents one of the methods that can be adopted for the synthesis of new anticancer mols. A series of novel antiproliferative agents designed by a pharmacophore hybridization approach, combining the arylcinnamide skeleton and an α-bromoacryloyl moiety, was synthesized and evaluated for its antiproliferative activity against a panel of seven human cancer cell lines. In addition, the new derivatives were also active on multidrug-resistant cell lines over-expressing P-glycoprotein. The biol. effects of various substituents on the N-Ph ring of the benzamide portion were also described. In order to study the possible mechanism of action, 2-Bromo-N-(3-{(1E)-3-oxo-3-[(4-morpholinophenyl)amino] prop-1-en-1-yl}phenyl)-acrylamide slightly increased the Reactive Oxygen Species (ROS) production in HeLa cells, but, more importantly, a remarkable decrease of intracellular reduced glutathione content was detected in treated cells compared with controls. These results were confirmed by the observation that only thiol-containing antioxidants were able to significantly protect the cells from induced cell death. Altogether the authors’ results indicate that the new derivatives are endowed with good anticancer activity in vitro, and their properties may result in the development of new cancer therapeutic strategies.

European Journal of Medicinal Chemistry published new progress about 1772-76-5. 1772-76-5 belongs to catalysis-chemistry, auxiliary class Benzenes, name is (E)-3-(3-Nitrophenyl)acrylic acid, and the molecular formula is C9H7NO4, Recommanded Product: (E)-3-(3-Nitrophenyl)acrylic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Sharnin, G. P. published the artcileIonization constants of nitro-substituted diphenylamine in dimethylformamide, Synthetic Route of 1821-27-8, the publication is Zhurnal Obshchei Khimii (1973), 43(7), 1564-9, database is CAplus.

Ionization constants were determined for 19 polynitro derivatives of Ph2NH and substituted Ph2NH in DMF and in aqueous sulfolane. The acidity of these amines increased with the number of NO2 groups present, o-NO2 groups having an especially large effect. In 2,4,2′-trinitro-4-R-substituted compounds, a correlation was observed between pKa and δ- of the R groups. The pKa’s of these compounds in DMF were lower than those in aqueous sulfolane.

Zhurnal Obshchei Khimii published new progress about 1821-27-8. 1821-27-8 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Amine,Benzene, name is Bis(4-nitrophenyl)amine, and the molecular formula is C3H6O2, Synthetic Route of 1821-27-8.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Hess, Kurth published the artcileSyntheses in the undecane series, COA of Formula: C10H20O2, the publication is Justus Liebigs Annalen der Chemie (1925), 151-6, database is CAplus.

Undecaue, C₁₁H₂₄, b₁₆ 79°, b₇₅₂ 194-5°, d₄^19.8 0.7418, n_D^19.5 1.41862, was prepared by reducing caprone, b₁₆ 107-8°, b₇₅₀ 226° (corrected), d₄²⁰ 0.8247, n_D¹⁹ 1.42916, m 14.5°, by boiling with amalgamated Zn in 1:1 HCl (HCl being passed through the solution for 24 hrs.) and also by reducing C₉H₁₁COMe. Reduction of 9.5 g. caprone with Na and EtOH gave 8.5 g. undecan-6-ol, b₁₆ 117-8°, b₇₅₄ 235° (corrected), m. 16°, d₄^21.8 0.8272, n_D¹⁹ 1.4370. Et butylacetoacetate (I), b₁₇ 114-5°, results in 19 g. yield from 19 g. AcCH₂CO₂Et, 22 g. BuBr, 3.4 g. Na and 40 cc. absolute EtOH (in addition to about 5 g. C₅H₁₁CO₂Et, b₁₆ 61-3°, d₄¹⁹ 0.8733, n_D^19.5 1.40785). Et dibutylacetoacetate (II), b₁₅ 135.5°, d₄²⁰ 0.9320, n_D20 1.44042, is formed in 5 g. yield from 10 g. I, 8 g. BuBr and 1.3 g. Na in 25 cc. absolute EtOH, heated 4 hrs. If 10.3 g. I, 9 g. BuBr and 1.3 g. Na in 16 g. EtOH are used, there results almost entirely Bu₂CHCO₂Et, b₁₆ 104°, d₄²⁰. 0.8631, n_D²⁰ 1.42223. II, heated 6 hrs. with 10% KOH, in equal volumes of H₂O and EtOH, gives ε-acetylnonane (III), b₁₆ 96-7°, d₄^18.4 0.8299, n_D^18.4 1.42795. There also results some dibutylacetic acid, b₁₆ 139-40, d₄^18.4 0.8978, n_D^17.4 1.43448. Reduction of III by Na and EtOH gives ε-nonylmethylcarbinol (ε-[1-hydroxyethyl]nonane), b₁₆ 108-9°, d₄^17.9 0.8392, n_D^18.2 1.44042, which is further reduced by amalgamated Zn and HCl to ε-ethylnonane (0.8 g. from 5.4 g. ketone), b₁₆ 71°, d₄^19.2 0.7513, n_D^19.5 1.42092.

Justus Liebigs Annalen der Chemie published new progress about 3115-28-4. 3115-28-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is 2-Butylhexanoic acid, and the molecular formula is C10H20O2, COA of Formula: C10H20O2.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

So, Wing Ho published the artcileOn-resin Ugi reaction for C-terminally modified and head-to-tail cyclized antibacterial peptides, Category: catalysis-chemistry, the publication is Organic Letters (2021), 23(21), 8277-8281, database is CAplus and MEDLINE.

Here we report a method to synthesize C-terminally modified peptides on resin. A four-component Ugi reaction of isocyanide resin, an Fmoc-protected (Fmoc = 9-fluorenylmethoxycarbonyl) amino acid, an amine, and a 6-nitroveratrylaldehyde gives C-terminal photo-caged peptide amides, which can be photolyzed to generate C-terminal peptide amides. Changing the amine component in the Ugi reaction gives peptides with different C-terminal modifications including substituted anilides, alkyne, and azide. By installing an N-terminal azide and C-terminal alkyne, we synthesized a head-to-tail cyclized antibacterial peptide through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The cyclized peptide exhibited higher proteolytic stability and antibacterial activity than the linear peptide.

Organic Letters published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C26H45N5O7Si2, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Li, Jia published the artcileCercosporin-bioinspired selective photooxidation reactions under mild conditions, Application of Bis(4-fluorophenyl)methane, the publication is Green Chemistry (2019), 21(22), 6073-6081, database is CAplus.

The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with mol. oxygen is a significant challenge in industrial chem. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.

Green Chemistry published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C13H10F2, Application of Bis(4-fluorophenyl)methane.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Guanti, Giuseppe published the artcileRegioselective synthesis of 1,8-dihydroxytetralins through a tandem reduction/intramolecular hydroxyalkylation of 4-(3-hydroxyphenyl)alkanoates, Name: 2-(3-(Benzyloxy)phenyl)acetic acid, the publication is Tetrahedron (1994), 50(41), 11945-66, database is CAplus.

A series of 4-(3-hydroxyphenyl)butanoates, e.g., 3-HOC₆H₄(CH₂)₃CO₂Et, has been prepared and transformed into 1,8-dihydroxytetralins, e.g., I, by treatment with 2 equiv of DIBALH followed by quenching with aqueous NH₄Cl. A possible mechanism for this novel, totally regioselective intramol. hydroxyalkylation is suggested and the factors affecting the stability of 1,8-dihydroxytetralins are also discussed.

Tetrahedron published new progress about 1860-58-8. 1860-58-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(3-(Benzyloxy)phenyl)acetic acid, and the molecular formula is C15H14O3, Name: 2-(3-(Benzyloxy)phenyl)acetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wietzoreck, M. published the artcileNitro- and oxy-PAHs in grassland soils from decade-long sampling in central Europe, Recommanded Product: Coronene, the publication is Environmental Geochemistry and Health (2022), 44(8), 2743-2765, database is CAplus and MEDLINE.

Long-term exposure to polycyclic aromatic hydrocarbons (PAHs) and their nitrated (NPAHs) and oxygenated (OPAHs) derivatives can cause adverse health effects due to their carcinogenicity, mutagenicity and oxidative potential. The distribution of PAH derivatives in the terrestrial environment has hardly been studied, although several PAH derivatives are ubiquitous in air and long-lived in soil and water. We report the multi-annual variations in the concentrations of NPAHs, OPAHs and PAHs in soils sampled at a semi-urban (Mokra, Czech Republic) and a regional background site (Kosetice, Czech Republic) in central Europe. The concentrations of the Σ₁₈NPAHs and the Σ₁₁₊₂OPAHs and O-heterocycles were 0.31 ± 0.23 ng g^-1 and 4.03 ± 3.03 ng g^-1, resp., in Kosetice, while slightly higher concentrations of 0.54 ± 0.45 ng g^-1 and 5.91 ± 0.45 ng g^-1, resp., were found in soil from Mokra. Among the 5 NPAHs found in the soils, 1-nitropyrene and less so 6-nitrobenzo(a)pyrene were most abundant. The OPAHs were more evenly distributed. The ratios of the PAH derivatives to their parent PAHs in Kosetice indicate that they were long-range transported to the background site. Our results show that several NPAHs and OPAHs are abundant in soil and that gas-particle partitioning is a major factor influencing the concentration of several semi-volatile NPAHs and OPAHs in the soils. Complete understanding of the long-term variations of NPAH and OPAH concentrations in soil is limited by the lack of kinetic data describing their formation and degradation

Environmental Geochemistry and Health published new progress about 191-07-1. 191-07-1 belongs to catalysis-chemistry, auxiliary class Electronic Materials, name is Coronene, and the molecular formula is C12H10N2O5, Recommanded Product: Coronene.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Naik, Ravi published the artcileMethyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism, COA of Formula: C12H16O3, the publication is Journal of Medicinal Chemistry (2017), 60(20), 8631-8646, database is CAplus and MEDLINE.

Previously, the authors reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chem. biol. approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. The authors hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c)as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.

Journal of Medicinal Chemistry published new progress about 1798-04-5. 1798-04-5 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ether, name is 2-(4-(tert-Butyl)phenoxy)acetic acid, and the molecular formula is C12H16O3, COA of Formula: C12H16O3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Naik, Ravi published the artcileMethyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism, Name: 2-(4-(Trifluoromethyl)phenoxy)acetic acid, the publication is Journal of Medicinal Chemistry (2017), 60(20), 8631-8646, database is CAplus and MEDLINE.

Previously, the authors reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chem. biol. approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. The authors hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c)as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.

Journal of Medicinal Chemistry published new progress about 163839-73-4. 163839-73-4 belongs to catalysis-chemistry, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Ether, name is 2-(4-(Trifluoromethyl)phenoxy)acetic acid, and the molecular formula is C9H7F3O3, Name: 2-(4-(Trifluoromethyl)phenoxy)acetic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia