Month: November 2022

Wester, Anita published the artcileEvaluation of 1H-Triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine in solution-phase and on-resin guanidinylation, Related Products of catalysis-chemistry, the publication is Journal of Organic Chemistry (2021), 86(21), 14371-14380, database is CAplus and MEDLINE.

Several guanidines and guanidinylated peptides have substantial potential as therapeutics, but efficient guanidinylation reagents are vital for easy access to these compounds Presently, pyrazole-1-carboxamidine type reagents are commonly used in the transformations of amines into corresponding guanidines. Here, we report a comparative study of the utility of 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine, which was synthesized in two steps and readily upscaled to gram amounts It exhibited excellent performance in solution-phase reactions, rapidly converting a set of representative aliphatic primary and unhindered secondary amines as well as aniline into the corresponding bis(tert-butoxycarbonyl)-protected guanidines. To enable a direct assessment of the reactivity of guanidinylation reagents, conversions were performed in deuterated solvents (d₇-DMF or d₈-THF), allowing for continuous anal. of the reaction mixtures by ¹H and ¹³C NMR. Likewise, 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine proved to be a versatile reagent in solid-phase conversions, for example, a resin-bound test peptide (KFFKFFK) was fully guanidinylated in only 2 h by using 2 equiv of the reagent per free amino group. Also, 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine proved capable of completely guanidinylating more sterically hindered N-terminal residues (e.g., N-Me amino acids or a peptoid) in resin-bound peptides. Its superior reactivity and stability demonstrated under heating conditions make 1H-triazole-1-[N,N’-bis(tert-butoxycarbonyl)]carboxamidine a valuable guanidinylation reagent both in solution- and solid-phase synthesis.

Journal of Organic Chemistry 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 C17H16O2, Related Products of catalysis-chemistry.

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

Guzelj, Samo published the artcileDiscovery of Desmuramylpeptide NOD2 Agonists with Single-Digit Nanomolar Potency, Synthetic Route of 1772-76-5, the publication is ACS Medicinal Chemistry Letters (2022), 13(8), 1270-1277, database is CAplus and MEDLINE.

The innate immune receptor nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) represents an important target for the development of structurally defined small mol. immunomodulatory compounds that have great potential to be used either as vaccine adjuvants or as general immunostimulatory agents. We report here the investigation of the structure-activity relationship of a series of novel desmuramylpeptide NOD2 agonists. Extensive exploration of chem. space culminated in the discovery of a lipophilic adamantane-moiety-featuring compound 40, the first single-digit nanomolar and the most potent NOD2 agonist in its structural class to date. Moreover, 40 acted synergistically with lipopolysaccharide and interferon-γ to induce the production of cytokines in human peripheral blood mononuclear cells and enhance their nonspecific cytotoxic activity against K562 cancer cells. These findings provide initial insight into its immunostimulatory potential, especially when used in combination with other immunopotentiators.

ACS Medicinal Chemistry Letters 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, Synthetic Route of 1772-76-5.

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

Hirajima, T. published the artcileFloatability of rare earth phosphors from waste fluorescent lamps, Computed Properties of 2016-56-0, the publication is International Journal of Mineral Processing (2005), 77(4), 187-198, database is CAplus.

Zeta-potential measurements were made to determine the elec. state of phosphor materials on the basis of which a feasibility study can be performed for the use of flotation in the recovery of fine (median size <13 μm) rare earth phosphors from waste fluorescent lamps. Tests were carried out on specimens of white (calcium halo-phosphate), red, green and blue (rare earth) phosphors in a 17:1:1:1 ratio of their mixture, and with actual waste phosphor materials. The effects of a cationic, dodecyl ammonium acetate (DAA), and two anionic, sodium dodecyl sulfate (SDS) and sodium oleate collectors on the floatability of materials, as well as that of Na₂SiO₃ dispersant on the separation characteristics, were investigated in different pH ranges. The process, applied to actual discarded waste phosphors gave, in a two-stage separation scheme, sink products assaying 17.7-23.8 and 21.5-25.9% rare earth phosphors for DAA and SDS flotation, resp. The recovery and Newton’s efficiency were about 70-90%/0.26-0.37 and 66-82%/0.18-0.20 for DAA and SDS flotation, resp.

International Journal of Mineral Processing published new progress about 2016-56-0. 2016-56-0 belongs to catalysis-chemistry, auxiliary class Active Esterification, name is Dodecylamineacetate, and the molecular formula is C14H31NO2, Computed Properties of 2016-56-0.

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

Hoque, Emdadul Md published the artcileIridium-Catalyzed Ligand-Controlled Remote para-Selective C-H Activation and Borylation of Twisted Aromatic Amides, Name: 2-Methylbenzoic acid, the publication is Angewandte Chemie, International Edition (2022), 61(27), e202203539, database is CAplus and MEDLINE.

A method of para-selective borylation of fully twisted aromatic amides ArCONBoc₂ is described, yielding boronamides 4-pinBC₆H_nX_4-nCONBoc₂ (X = alkyl, alkoxy, aryl, halo, CN). The borylation proceeded via an unprecedented substrate-ligand distortion between the twisted aromatic amides and a newly designed ligand framework, 4,5-diaza-9H-fluorene (defa) that is different from the traditionally used ligand (dtbpy) for the C-H borylation reactions. The designed ligand defa has led to the development of a new type of catalytic system that shows excellent para selectivity for a range of aromatic amides. Moreover, the designed ligand has shown excellent reactivity and selectivity for a range of heterocyclic aromatic amides. The identification of key transition states and intermediates using the DFT computations associated with the three regio-isomeric pathways revealed that the most efficient catalytic pathway with the defa ligand leads to the para borylation while in the case of bpy the borylation at the para and meta sites compete.

Angewandte Chemie, International Edition published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Name: 2-Methylbenzoic acid.

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

Renaud, Johanne published the artcileSelective Estrogen Receptor Modulators with Conformationally Restricted Side Chains. Synthesis and Structure-Activity Relationship of ERα-Selective Tetrahydroisoquinoline Ligands, Formula: C15H14O3, the publication is Journal of Medicinal Chemistry (2005), 48(2), 364-379, database is CAplus and MEDLINE.

The authors disclose herein the discovery of estrogen receptor α (ERα) selective estrogen receptor modulators (SERMs) of the tetrahydroisoquinoline series that incorporate novel conformationally restricted side chains as replacement of the aminoethoxy residue typical of SERMs. Mol. modeling studies used in conjunction with the x-ray crystal structure of the ERα ligand binding domain (LBD) with raloxifene (7) suggested a diazadecaline moiety as a viable mimic of the SERM side chain. On the basis of this knowledge, the piperidinylethoxy moiety of our lead compound I was replaced by a diazadecaline subunit, providing the novel tetrahydroisoquinoline II. In addition to exhibiting a binding affinity to ERα and antagonistic properties in the estrogen response element and MCF-7 assays similar to those of the parent compound I, ligand II showed a reduced agonist behavior in the MCF-7 assay in the absence of 17β-estradiol. These data point toward the fact that II may have a potential for breast cancer prevention/treatment in vivo, a feature which is particularly attractive in the quest for safe alternatives to hormone replacement therapy. In a pharmacokinetic experiment carried out in rats, II displayed an interesting profile, with a bioavailability of 49%. The authors also disclose the x-ray crystal structure of II in complex with ERα-LBD, which reveals the preferred configurations of II at the two chiral centers and the details of its interactions with the receptor. Finally, our structure-activity relationship studies show that other analogs bearing constrained side chains retain potency and antagonist activity and that a 3-OH substituted Ph D-ring increases the selectivity of a set of piperazinyl-containing ligands in favor of ERα over ERβ.

Journal of Medicinal Chemistry 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, Formula: C15H14O3.

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

Wang, Haotian published the artcileIn-Tube Passive Dosing of Hydrophobic Organic Chemicals: Controlling Freely Dissolved Concentrations in Flow-Through and Large-Volume Experiments, Computed Properties of 613-33-2, the publication is Environmental Science & Technology Letters (2022), 9(4), 339-344, database is CAplus.

Passive dosing is increasingly used to control exposure concentrations of hydrophobic organic chems. (HOCs) in small-sized aquatic tests. This study introduces in-tube passive dosing to control HOC exposure in larger test volumes and flow-through experiments Water was dosed by passing it through a tube holding HOC-loaded silicone rods. We equipped a 6 m PTFE tube (ID 10 mm) with four parallel silicone rods (OD 3 mm) to accommodate water flows from 0.2 to 120 L/h and developed a mass transfer kinetic model to capture the chemodynamics in the system. The first experiment was conducted with fluoranthene to determine the dosing kinetics, reproducibility, and long-term performance of the system. Aqueous concentrations were measured by mol. fluorescence at different flows and positions within the tube. The second experiment was conducted with a complex petroleum mixture (cracked gas oil). Concentrations of 22 mixture constituents were measured by solid phase microextraction coupled to GC-MS. Overall, the system provided stable and reproducible water concentrations, which were at equilibrium for flows less than 10 mL/min and at steady state for higher flows. Fluoranthene concentrations declined less than 20% when dosing 1 m³ during 1 wk. The mass transfer kinetic model can now be used to scale the system for various applications.

Environmental Science & Technology Letters published new progress about 613-33-2. 613-33-2 belongs to catalysis-chemistry, auxiliary class Benzene, name is 4,4′-Dimethyldiphenyl, and the molecular formula is C18H28N2O7, Computed Properties of 613-33-2.

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

Hua, Yun-Yu published the artcileIridium-Catalyzed Asymmetric Hydrogenation of γ- and δ-Ketoacids for Enantioselective Synthesis of γ- and δ-Lactones, Related Products of catalysis-chemistry, the publication is Organic Letters (2020), 22(3), 818-822, database is CAplus and MEDLINE.

A highly efficient asym. hydrogenation of γ- and δ-ketoacids was developed by using a chiral spiro iridium catalyst, affording the optically active γ- and δ-hydroxy acids/lactones in high yields with excellent enantioselectivities (up to >99% ee) and turnover numbers (TON up to 100000). This protocol provides an efficient and practical method for enantioselective synthesis of Ezetimibe.

Organic Letters published new progress about 2051-95-8. 2051-95-8 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Ketone, name is 3-Benzoylpropionicacid, and the molecular formula is C10H10O3, Related Products of catalysis-chemistry.

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

Dekkers, Bart G. J. published the artcileRelevance of the drug-drug interactions between lidocaine and the pharmacokinetic enhancers ritonavir and cobicistat, Related Products of catalysis-chemistry, the publication is AIDS (London, United Kingdom) (2019), 33(6), 1100-1102, database is CAplus and MEDLINE.

Reporting on the serol. response to syphilis treatment with penicillin benzathine or doxycycline in patients with HIV following a manufacturing shortfall of penicillin benzathine. Discomfort of these injections can be reduced by replacing part of the solvent by a lidocaine (lignocaine) solution To enhance exposure to antiretroviral drugs, such as atazanavir, darunavir and elvitegravir, ritonavir and cobicistat are used as boosters in combined antiretroviral therapy. Ritonavir and cobicistat inhibit CYP3A4, resulting in an increased exposure (increased area under the curve) , increased maximum concentration (Cmax) and increased half-life 1/2 of antiretroviral drugs that are substrates of CYP3A4. Drug-drug interactions between ritonavir or cobicistat and lidocaine have been suggested to increase lidocaine exposure by more than three-fold complicating treatment with benzylpenicillin benzathine as this interaction may lead to higher plasma lidocaine levels and adverse effects, including neurol. and cardiac side effects.

AIDS (London, United Kingdom) published new progress about 140-28-3. 140-28-3 belongs to catalysis-chemistry, auxiliary class Benzenes, name is N1,N2-Dibenzylethane-1,2-diamine, and the molecular formula is C16H20N2, Related Products of catalysis-chemistry.

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

Fluck, Ekkehard published the artcile[1,3,4]Thiazaphospholidines. IV. [1,3,4]Thiazaphospholidine sulfide and oxide, ethynylaminophosphine, Recommanded Product: 1,1-Dimethylthiourea, the publication is Phosphorus, Sulfur and Silicon and the Related Elements (1994), 90(1-4), 59-78, database is CAplus.

The synthesis of the ethynylaminophosphines, PhCCP(R)(NEt₂) (1, R = NEt₂; 2, R = Ph; 3, R = cyclohexyl), RCCP(Ph)(NEt₂) (4, R = Bu; 5, R = SiMe₃) from substituted alkynylmagnesium bromides and haloaminophosphantes is described. Reaction of 1 with urea derivatives yields the [1,3,4]thiazaphospholidines. 2 Reacts with thiouracil to give thiazaphospholidine I, with 2-mercaptobenzimidazole to give compound II and 3 reacts with 2-mercaptobenzimidazole to give similar benzoimidazothiazaphosphole. The new [1,3,4]thiazaphospholidines can be transferred into the corresponding sulfides by heating with elemental sulfur or into their oxides by treatment with tert-Bu hydroperoxide. The spirocyclic compound III is the product from the reaction with o-chloranil. All new ethynylaminophosphines, [1,3,4]thiazaphospholidines and their sulfides and oxides are characterized by NMR, mass and IR spectra. X-ray structure analyses of I and related compounds were performed.

Phosphorus, Sulfur and Silicon and the Related Elements published new progress about 6972-05-0. 6972-05-0 belongs to catalysis-chemistry, auxiliary class Thiourea,Amine,Aliphatic hydrocarbon chain,Amide, name is 1,1-Dimethylthiourea, and the molecular formula is C3H8N2S, Recommanded Product: 1,1-Dimethylthiourea.

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

Dvoretsky, Alexander G. published the artcileFatty acids in the circulatory system of an invasive king crab from the Barents Sea, Safety of Docosahexaenoic Acid, the publication is Journal of Food Composition and Analysis (2022), 104528, database is CAplus.

We assayed fatty acids in the cardiac muscle and hemolymph of adult crabs collected in the coastal Barents Sea. Polyunsaturated fatty acids were the major fatty acids (273μg mL^-1 or 42.8% in the hemolymph and 3130μg g^-1 or 59.7% in the cardiac muscle) followed by saturated fatty acids (201μg mL^-1 or 33.9% and 1290μg g^-1 or 24.8%, resp.) and monounsaturated fatty acids (143μg mL^-1 or 23.3% and 815μg g-1 or 15.6%, resp.). The n-3/n-6 ratios in these tissues were 3.4 and 4.3, resp. Fatty acid profiles were similar in females and males, in crabs with different shell conditions and in different-sized crabs. The crabs captured on soft bottoms contained significantly higher concentrations of fatty acids in their hemolymph than the crabs from hard bottoms probably owing to differences in their diets. In general, fatty acid levels in the cardiac muscle were 1.5-3 times higher than in the leg muscle reflecting higher functional load of the heart compared to walking legs. We suggest that both byproducts that now are discarded during red king crab processing could be considered addnl. sources for extracting valuable n-3 fatty acids.

Journal of Food Composition and Analysis published new progress about 6217-54-5. 6217-54-5 belongs to catalysis-chemistry, auxiliary class Alkenyl,Carboxylic acid,Aliphatic hydrocarbon chain,Metabolic Enzyme,RAR/RXR,Natural product, name is Docosahexaenoic Acid, and the molecular formula is C22H32O2, Safety of Docosahexaenoic Acid.

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