Ketones
They play a crucial role in various biological processes, including energy metabolism and signaling pathways.
Ketones can be produced naturally in the body during states of fasting, exercise, or low-carbohydrate diets, and have been studied for their potential therapeutic applications in conditions like diabetes, neurological disorders, and cancer.
Researchers continue to investigate the mechanisms by which ketones impact human health and explore the development of ketone-based supplements and therapies to optimize their benefits.
Most cited protocols related to «Ketones»
In general, quantum mechanics population analysis methods distribute the total electron density of a molecule into partial charges centered on each atom of the molecule. As partial charges are not observables, there are different ways to partition the electron density. The CM1A method uses the Mulliken population analysis from the electron density obtained by the AM1 method from the ligand geometry. Mulliken charges for an atom A are computed using the following equation: where is the partial Mulliken charge, is the nuclear charge of the atom A and is the electron density assigned to atom A as described by the equation:
where N is the total number of electrons in the molecule, is the molecular orbital coefficient for the atomic orbital and is the QM overlap integral. This electron density definition is based on the linear combination of atomic orbital–molecular orbital (LCAO–MO) method where the molecular electronic distribution per each molecular orbital is defined each as a linear combination of atomic orbitals (n).
The CM1A charges are then computed using a multilinear transformation of the Mulliken charges based in the computed bond orders to improve the molecular dipole moment using empirical parameters. Then, for neutral molecules, the 1.14*CM1A model scales the charges by a factor 1.14, which was fitted to improve the agreement of the HFEs to the experimental values (16 (link)). If the total charge of the molecule is not zero, partial charges are not scaled. It should be noted that, as in all quantum mechanics based charges, the CM1A charges can have some variations due to the molecular geometry. The typical variations observed in our tests are in the 0.03–0.05 e range, with a few cases involving intramolecular hydrogen bonds reaching 0.1e.
A later evaluation of HFEs for a set of 426 organic molecules showed that some moieties such as phenyl rings, aldehydes or ketones are not well parameterized by the 1.14*CM1A charge model, leading to a mean unsigned error (MUE) of 1.5 kcal/mol with respect to experimental HFE data. The performance of CM1A charges was improved by adding Localized Bond Charge Corrections (LBCC), by which small charge adjustments are made to the partial charges for atoms in problematic bond types such as, CT-OH in aliphatic alcohols. Only 19 LBCCs were enough to reduce the errors with the 1.14*CM1A charges for the 426 HFE values to only 0.61 kcal/mol. These adjustments give rise to the 1.14*CM1A-LBCC charge method which can also be provided by the LigParGen server.
All experiments with SARS-CoV-2 were performed in enhanced biosafety level 3 (BSL3) containment laboratories at the University of Tokyo, which are approved for such use by the Ministry of Agriculture, Forestry, and Fisheries, Japan, or in enhanced BSL3 containment laboratories at the University of Wisconsin-Madison, which are approved for such use by the Centers for Disease Control and Prevention and by the US Department of Agriculture.
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Microbial activity in each microplate was expressed as average well color development (AWCD). Substrate richness values (R) were calculated as the number of utilized substrates and evenness were calculated according to Zak et al. [26 (link)] (Table
Formulae for calculations
Index | Definition | Formulae | Definitions |
---|---|---|---|
Average well color development | AWCD = Σ ODi/31 | pi = proportional color development of the well over total color development of all wells of a plate H = Shannon index of diversity S = number of wells with color development (substrate utilization richness) | |
Shannon diversity | Measure of richness | H = −Σpi(lnpi) | |
Shannon evenness | Evenness calculated from Shannon index | E = H/lnS |
Most recents protocols related to «Ketones»
Example 26
Synthesis of 169-A.
A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (750 mg, 3.54 mmol), 1-methylpiperidin-4-one (800 mg, 7.08 mmol) and acetic acid (2 drops) in DCE (15 mL) was stirred at 50° C. for 2 h. Then Sodium triacetoxyborohydride (1.50 g, 7.08 mmol) was added into above mixture and stirred at 50° C. for another 2 h. After the reaction was completed according to LCMS, the solvent was diluted with water (10 mL) and then extracted by DCM (10 mL×3). The combined organics washed with brine (10 mL×3), dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜50:1) to give 169-A (750 mg, 69%) as a yellow oil.
Synthesis of 169-B.
A solution of 169-A (400 mg, 1.29 mmol) in DCM (10 mL) was added TFA (5 mL) and stirred at room temperature for 1 h. when LCMS showed the reaction was finished. The solvent was removed in vacuo to give 169-B as a crude product and used to next step directly.
Synthesis of 169-C.
A mixture of 143-C (306 mg, 0.65 mmol) and 169-B (crude product from last step) in acetonitrile (6 mL) was stirred at 50° C. for 30 min. Then Na2CO3 (624 mg, 6.50 mmol) was added into above mixture and stirred at 50° C. for 3 h. After the reaction was completed according to LCMS, the mixture was cooled to room temperature. The Na2CO3 was removed by filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜20:1) to give 169-C (230 mg, 76%) as a yellow solid.
Synthesis of 169.
A mixture of 169-C (230 mg, 0.49 mmol) and Pd/C (230 mg) in MeOH (10 mL) was stirred at room temperature for 30 min under H2 atmosphere. Pd/C was then removed by filtration through the Celite. The filtrate was concentrated and the residue was purified by Pre-TLC (DCM:MeOH=10:1) to give 169 (150 mg, 70%) as a white solid.
Compounds 152, 182, 199, 201, 202, 203, 235, 236 and 256 were synthesized in a similar manner using the appropriately substituted aldehyde or ketone variant of 169.
Compound 152.
50 mg, 36%, a light yellow solid.
Compound 182.
70 mg, 38%, a red solid.
Compound 199.
50 mg, 54%, a light yellow solid.
Compound 201.
30 mg, 42%, as a yellow solid.
Compound 202.
30 mg, 42%, a yellow solid.
Compound 203.
30 mg, 18%, a yellow solid.
Compound 235.
170 mg, 87%, a white solid.
Compound 236.
70 mg, 50%, a white solid.
Compound 256.
20 mg, 8%, a light yellow solid.
Compounds 210, 211, 215, 222, 223, 242 and 262 were synthesized in a similar manner using the appropriately substituted amine variant of 169.
Compound 210.
160 mg, 96%, a tan solid.
Compound 211.
70 mg, 40%, a white solid
Compound 215.
70 mg, 75%, a white solid.
Compound 222.
30 mg, 42%, a yellow solid.
Compound 223.
35 mg, 31%, a white solid.
Compound 242.
50 mg, 34%, a white solid.
Compound 262.
38 mg, 43%, a white solid.
Example 125
Methyl 4-((5-(benzyloxy)-2-methoxyphenyl)(ethyl)amino)butanoate (184). 5-(Benzyloxy)-N-ethyl-2-methoxyaniline (146) (0.681 g, 2.65 mmol), DIEA (0.92 mL, 5.3 mmol), and methyl 4-iodobutyrate (0.72 mL, 5.3 mmol) in DMF (5 mL) were stirred at 70° C. for 5 days. The reaction mixture was cooled to rt, diluted with EtOAc (60 mL), washed with water (4×50 mL), brine (75 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 184 (0.72 g, 76%) as a dark amber oil.
Methyl 4-(ethyl(5-hydroxy-2-methoxyphenyl)amino)butanoate (186). Ester 184 (0.72 g, 2.0 mmol) was stirred under reflux with 6 mL of water and 6 mL of conc HCl for 1.5 hrs and then evaporated to dryness to give acid 185 as a brown gum. The crude acid was dissolved in 50 mL of methanol containing 1 drop (cat.) of methanesulfonic acid ant the solution was kept for 2 hrs at rt. After that the mixture was concentrated in vacuum and the residue was mixed with 20 mL of saturated NaHCO3. The product was extracted with EtOAc (3×40 mL). The extract was washed with brine (40 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 186 (0.444 g, 83%) as a brown oil.
N-(6-(dimethylamino)-9-(4-(ethyl(4-methoxy-4-oxobutyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (187). To a stirred suspension of tetramethylrhodamine ketone 101 (0.234 g, 0.830 mmol) in 10 mL of dry chloroform was added oxalyl chloride (72 μL, 0.82 mmol) upon cooling to 0-5° C. The resulting red solution was stirred for 0.5 h at 5° C., and the solution of compound 186 (0.222 g, 0.831 mmol) in dry chloroform (5 mL) was introduced. The reaction was allowed to heat to rt, stirred for 72 h, diluted with CHCl3 (100 mL and washed with sat. NaHCO3 solution (2×30 mL) The organic layer was extracted with 5% HCl (3×25 mL). The combined acid extract was washed with CHCl3 (2×15 mL; discarded), saturated with sodium acetate and extracted with CHCl3 (5×30 mL). The extract was washed with brine (50 mL), dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with CHCl3/MeOH/AcOH/H2O (100:20:5:1)), eluant: CHCl3/MeOH/AcOH/H2O (100:20:5:1) to give the product 187 (0.138 g, 29%) as a purple solid.
4-((4-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-hydroxy-2-methoxyphenyl)(ethyl)amino)butanoate (188). Methyl ester 187 (0.136 g, 0.240 mmol) was dissolved in 5 mL of 1M KOH (5 mmol). The reaction mixture was kept at rt for 1.5 hrs and the acetic acid (1 mL) was added. The mixture was extracted with CHCl3 (4×30 mL), and combined extract was washed with brine (20 mL), filtered through the paper filter and. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with MeCN/H2O (4:1)), eluant: MeCN/H2O/AcOH/(4:1:1) to give the product 188 (0.069 g, 98%) as a purple solid.
N-(6-(dimethylamino)-9-(4-((4-(2,5-dioxopyrrolidin-1-yloxy)-4-oxobutyl)(ethyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (189). To a solution of the acid 188 (69 mg, 0.12 mmol) in DMF (2 mL) and DIEA (58 μL, 0.33 mmol) was added N-hydroxysuccinimide trifluoroacetate (70 mg, 0.33 mmol). The reaction mixture was stirred for 30 min, diluted with chloroform (100 mL) and washed with water (5×50 mL), brine (50 mL), filtered through paper and concentrated in vacuum. The crude product was purified by precipitation from CHCl3 solution (5 mL) with ether (20 mL) to give compound 189 (55 mg, 67%) as a purple powder.
Example 3
Cyclohexene (1a) and polar organic solvent, preferably acetonitrile in (1:2 to 1:10 weight ratio with respect to the substrate) was taken in to a 60 ml vessel. Further, the bare graphene oxide as photocatalyst (1 to 10 mol % of the substrate) was added and the resulting mixture was saturated with CO2 by purging at 1 atm pressure. The reaction vessel was sealed and irradiated with 20 W LED light (Model No. HP-FL-20 W-F, Hope LED Opto-Electric CO., Ltd) for 24 h. The intensity of the LED light at the reaction flask was measured to be 86 W/m2 by intensity meter. The conversion of the olefin was examined by GC-FID based on the unreacted substrate. The selectivity of the α,β-unsaturated hydroxyl or carbonyl compounds was determined by GC-MS. The conversion of olefin and the selectivity towards the corresponding α,β-unsaturated hydroxyl and ketone is given in the Table 1, entry 3.
Example 101
Compound 104. To a stirred suspension of ketone 101 (94 mg, 0.333 mmol) in dry chloroform (10 mL), oxalyl chloride (30 μL, 0.33 mmol) was added upon cooling to 0-5° C. The resulted red solution was stirred for 1 h, then N,N-diethyl-m-anisidine (60 mg, 0.33 mmol) was added. The reaction was allowed to warm to rt, stirred for 16 h and diluted with CHCl3 (60 mL). Chloroform solution was shaken with sat. NaHCO3 (40 mL) until water layer turned almost colorless. The organic layer was washed with sat. NaHCO3 (20 mL) and extracted with 10% HCl (2×30 mL). The combined acid extract was washed with CHCl3 (2×15 mL; discarded), the aqueous solution was saturated with sodium acetate and extracted with CHCl3 (4×30 mL). The extract was washed with brine (30 mL), and evaporated. The crude product was purified by chromatography on silica gel column (2×40 cm bed, packed with 10% MeOH and 1% AcOH in CHCl3) eluant: 10% MeOH and 1% AcOH in CHCl3 to give the product 104 (3 mg, 2%) as a purple wax.
Example 23
-
- A composition comprising:
- about 0.01% to 3.0% of a plurality of functionalized metallic nanofibers, substantially all of the metallic nanofibers having at least a partial coating of a polyvinyl pyrrolidone polymer;
- about 0.5% to 5.0% polyimide; and
- with the balance comprising a ketone, including diketones and cyclic ketones, such as cyclohexanone, cyclopentanone, cycloheptanone, cyclooctanone, acetone, benzophenone, acetylacetone, acetophenone, cyclopropanone, isophorone, methyl ethyl ketone, or mixtures thereof.
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More about "Ketones"
These versatile molecules play a crucial role in various biological processes, including energy metabolism and signaling pathways.
Ketones can be produced naturally in the body during states of fasting, exercise, or low-carbohydrate diets, and have been studied for their potential therapeutic applications in conditions like diabetes, neurological disorders, and cancer.
Researchers continue to investigate the mechanisms by which ketones impact human health and explore the development of ketone-based supplements and therapies to optimize their benefits.
Ketones are closely related to other important biomolecules like trypsin, a proteolytic enzyme crucial for digestion, and FBS (Fetal Bovine Serum), a widely used cell culture supplement.
TPCK-trypsin, a chemically modified form of trypsin, is also used in research applications.
The Precision Xtra device is a popular tool for measuring ketone levels in the body, providing valuable insights into an individual's metabolic state.
Additionally, antimicrobial agents like penicillin and streptomycin are often used in cell culture media, such as Opti-MEM and DMEM, to prevent bacterial contamination.
Bovine serum albumin (BSA) is another common component of cell culture media, serving as a protein source and growth supplement.
By understanding the intricacies of ketones and their relationship to these other biomolecules and research tools, scientists and healthcare professionals can develop more effective strategies for optimizing human health and unlocking the full potential of ketone-based therapies.
Whether you're a researcher, a healthcare provider, or an individual interested in the science of ketones, this comprehensive overview can help you navigate the complex world of these fascinating compounds.