Awesome Chemistry Experiments For C16H19NO5

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Synthesis of jadomycin A and related jadomycin aglycons: structural re-examination of jadomycins S and T may be needed

Jadomycin A and related jadomycin M and W aglycons were synthesized. Easy re-construction of 4(hydroxymethyl)-1,3-oxazolidin-5-one system into an isomeric 1,3-oxazolidine-4-carboxylic acid system during the synthetic trial of jadomycin S aglycon requests us to more precisely re-examine the structures proposed for jadomycins S and T, derived from hydroxyl-containing amino acids of L-serine and L-threonine, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Novel Microwave Assisted Synthesis and Antimicrobial Activity of New Quinolone-Hybrids

Background: Carbo(thio)amid derivatives 4a, 4b were obtained starting from nalidixic acid in three steps. The acidic treatment of compound 4a generated the corresponding 1,3,4-oxadiazole (5), while the compound 4a gave 1,2,4-triazole derivatives 8a, 8b in basic media. The condensation of 4a with ethyl bromoacetate and 4-chlorophenacyl bromide afforded 1,3-oxazolidine, 6 and 1,3-thiazolidine, 7 derivatives. The synthesis of Mannich bases of 9-15 and 17-19 were achieved from the reaction of 1,2,4-triazoles, 8a, 8b and 1,3,4-oxadiazole, 16, with several heterocyclic amines that has biological activity. Methods: In this article, a series of triazole or 1,3,4-oxadiazole rings containing some novel biologically active quinolone derivatives. Conventional and microwave assisted methods were used for all syntheses. Moreover, the effect of acid catalyst on Mannich reactions was investigated. The structures of newly synthesized compounds were elucidated on the basis of H-1 NMR, C-13 NMR, FT IR, EI MS techniques and elemental analysis. All these compounds were screened in vitro for their antimicrobial activity against various gram-positive and gram-negative bacterial and fungal strains. Results: This study reports the successful synthesis of some new hybrid compounds starting from nalidixic acid. Two methods containing conventional and microwave assistance with/without catalyst were used to obtain the target compounds. Microwave assistance supplied more efficient way leading the formation of target compounds. Moreover, the effect of acid catalyst on Mannich reactions was investigated. The antimicrobial activity screening studies were also performed in the study. Conclusion: The antimicrobial screening suggests that the compounds containing norfloxacin (9a,b and 17), ciprofloxacin (10a,b and 18) or 7-aminocephalosporanic (12) acid nucleus displayed excellent antimicrobial activity. Moreover, some of them (5-7, 8-13, 15-18) displayed inhibition properties on Escherichia coli (Ec) and Mycobacterium smegmatis (Ms) better from ampicillin or streptomycin with the mic value 0.24 mu g/mL.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels. 84793-24-8, Name is Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate, molecular formula is C16H19NO5. In an article, author is Goncalves, Raoni S. B.,once mentioned of 84793-24-8, Quality Control of Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate.

Crystal structures of mefloquine-oxazolidine derivatives, 4-[3-(halophenyl)hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]2,8-bis(trifluoromethyl)quinolines

Crystal structures are reported for five racemic 4-{3-(halophenyl)hexahydro[1,3]oxazolo [3,4-a]pyridin-1- yl)-2,8-bis(triffuoromethyl)quinolines, 2, namely (2: X = 2-F, 3-Br, 4-C1 4-Br and 4-F), prepared from metloquine and XC6H5CHO. In each case, the compound crystallizes in the triclinic space group. P (1) over bar, with Z = 2. All molecules have F shapes with the X-phenyl and quinoline rings lying on one side of the best plane through the fused oxazolidinc-piperidine rings. Differences in the conformations of the molecules are indicated by the differences in the interplanar angles. In each case, the supramolecular arrangements are made up from combinations of a a and some of C-H X and C-X pi (X = halo) interactions. Two similar structural sub-sets found in the crystal structures of the five derivatives are centrosymmetric a-linked dimers and centrosvmmetric cage-like dimers. The cage-like dimers, formed by the intermeshing of the rings of the monomers, are generated from different weak intermolecular interactions, which include C-H… X and C-X (X = halo) interactions. Comparisons are made between the activities of the mefloquine-oxazolidine derivatives in in-vitro tests against the multidrug-resistant tuberculosis strain and conformations, as measured by interplanar angles.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Chun, Jiong, once mentioned the application of 84793-24-8, Name is Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate, molecular formula is C16H19NO5, molecular weight is 305.3258, MDL number is MFCD00272296, category is oxazolidines. Now introduce a scientific discovery about this category, SDS of cas: 84793-24-8.

Synthesis of new ceramide analogues with allene in the sphingoid backbone

Ceramide is an important sphingolipid which can mediate a diverse range of biological activities. New ceramide analogues with an allene group in the sphingoid backbone were synthesized. The synthesis of the key intermediates involved the LiAlH(4)reduction of oxazolidine intermediates via a directed reduction-elimination reaction. Hydrolysis of the oxazolidine, liberation of the amino group, andN-acylation provided new ceramide analogues. These new analogues may provide new resources to study their bioactivities and the structure-activity relationship.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Related Products of 84793-24-8, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 84793-24-8, Name is Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate, SMILES is O=C(OCC)[C@@H](N([C@H]1C)C(OC1=O)=O)CCC2=CC=CC=C2, belongs to oxazolidines compound. In a article, author is Cui, Qianling, introduce new discover of the category.

Thermosensitive Behavior of Poly(ethylene Glycol)-Based Block Copolymer (PEG-b-PADMO) Controlled via Self-Assembled Microstructure

Stimuli-responsive, well-defined diblock copolymers (PEG-b-PADMO) comprising poly(ethylene glycol) (PEG, DP (degree of polymerization) = 45) as the hydrophilic and temperature-sensitive part and poly(N-acryloyl-2,2-dimethyl-1,3-oxazolidine) (PADMO, DP = 18-47) as the hydrophobic and acid-labile part self-assembled in water into spherical micelles with high aggregation number. The micellar structures and thermally induced phase transitions of the copolymers were investigated with (1)H NMR spectroscopy, light scattering, microscopy, turbidimetry, and fluorescence techniques. Thermoresponsive phase transitions of the copolymers in water were controlled via formation of core shell-type micelles with densely compact PEG corona. Their lower critical solution temperatures (LCSTs) were modulated within the range 40-72 degrees C by varying PADMO block length. This unusually low LCST was attributed to the densely packed PEG structure in the polymer micelles, which resulted in strong n-clustering attractive interactions and insufficient hydration of PEG chains in the shell and greatly enhanced the thermosensitivity. The LCST behavior can also be modulated by partial acid hydrolysis of PADMO segments through the resulting change of hydrophobicity.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Assessing the Structure of Octastate Molecular Switches Using H-1 NMR Density Functional Theory Calculations

Density functional theory calculations are used to reveal the relationships between the structures, energies, and NMR signatures of an octastate molecular switch composed of a dithienylethene (DTE) unit covalently linked to an indolino[2,1-b]oxazolidine (BOX) moiety through an ethylenic junction. Both the DTE and BOX moieties can adopt open or closed forms. The ethylenic junction can be Z or E, but the latter has been confirmed to be, by far, more stable than the former for all BOX/DTE combinations. In addition, when the DTE is open, the two thienyl units can fold to form parallel conformers, by opposition to the antiparallel or unfolded conformers. Usually parallel conformers present a higher energy than the antiparallel ones, but in the case of compound 2 having a bulky substituent (R = pPh-SMe) on the terminal thienyl group, the enthalpy of one conformer is very close (1-2 kJ mol(-1)) to that of the most stable antiparallel one, making photocyclization less efficient. These conformational differences and the presence of parallel DTE forms have been substantiated by analyzing experimental H-1 NMR chemical shifts in light of their calculated values. These H-1 NMR chemical shift calculations led to the following statements: (i) Going from state I (DTE open, BOX closed) to state II (both DTE and BOX are open) the H-8 proton of compound 1 (R = Me) is deshielded by similar to 0.15 ppm. (ii) The deshielding of H-8 proton of compound 2 is larger and attains 0.41 ppm whereas H-7 is more shielded by 0.11 ppm. (iii) Then, going from compound 1 to compound 2 leads to deshielding of both H-7 and H-8 protons. As a consequence, the difference of photochromism gating efficiency among compounds 1, 2, and 3 (R = pPh-OMe) can be attributed to the stabilization of parallel conformer due to an establishment of an intramolecular interaction with BOX opening.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Induction of maize glutathione S-transferase by herbicide safener and their effect on enzyme activity against chlorsulfuron

The acetolactate synthase(ALS) activity, glutathione S-transferase(GST) activity and glutathione(GSH) content in maize was investigated in response to treatments with safener (S)-3-dichloroacety1-2,2-dimethyl-4-ethyl-1,3-oxazolidine. When induced by the chiral compound, the GSH content in root and shoot of maize increased 91.10% and 71.66%, respectively, the recovery rate of ALS activity reached 77%, and the GST activity increased 103.77%. The activity of maize GST was also assayed towards chlorsulfuron in vitro; the results showed that the induction of GST activity against chlorsulfuron of 14.54% was obtained. The enhancement of GST activity was found to be concomitant with changes in kinetic constants, which was related directly to the enzyme affinity for the CDNB substrate.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

Extracurricular laboratory: Discover of Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate

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Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines

A diastereoselective mercury(II)-promoted intramolecular cyclization of unsaturated aldehyde via an oxazolidine to prepare C-3-substituted tetrahydroisoquinoline is disclosed. The C-3 stereogenic center is subsequently exploited to create the C-1 stereocenter by coordination of the nudeophilic reagent to the oxygen atom of oxazolidine. Both cis- and trans-1,3-disubstituted tetrahydroisoquinolines can be readily prepared. In addition, when a cationic rhodium complex was used, intramolecular hydroamination was effected, thus avoiding mercury(II) salts and demercuration. The reaction is general and works well using aliphatic and aromatic aldehydes.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Stereoselective Syntheses and Application of Chiral Bi- and Tridentate Ligands Derived from (+)-Sabinol

A library of bidentate diols, as well as tridentate triols and aminodiols, derived from (+)-sabinol, was synthesized in a stereoselective manner. Sabinol was transformed into allylic trichloroacetamide via Overman rearrangement of the corresponding trichloroacetimidate. After changing the protecting group to Boc, the enamine was subjected to stereospecific dihydroxylation with OsO4/NMO, resulting in the (1R, 2R, 3R, 5R)-aminodiol diastereomer. The obtained primary aminodiol was transformed to a secondary analogue. The ring closure of the N-benzyl-substituted aminodiol with formaldehyde was investigated and regioselective formation of the spiro-oxazolidine ring was observed. Hydroboration or dihydroxylation of sabinol or its benzyl ether with OsO4/NMO resulted in the formation of sabinane-based diols and triols following a highly stereospecific reaction. Treatment of sabinol with m-CPBA afforded O-benzoyl triol as a diastereoisomer of the directly dihydroxylated product, instead of the expected epoxy alcohol. The resulting aminodiols, diol, and triols were applied as chiral catalysts in the reaction of diethylzinc and benzaldehyde from moderate to good selectivity.

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem

 

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Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, Product Details of 84793-24-884793-24-8, Name is Ethyl (S)-2-[(S)-4-Methyl-2,5-dioxo-3-oxazolidinyl]-4-phenylbutanoate, SMILES is O=C(OCC)[C@@H](N([C@H]1C)C(OC1=O)=O)CCC2=CC=CC=C2, belongs to oxazolidines compound. In a article, author is Wang, Yanmei, introduce new discover of the category.

Synthesis of Amphiphilic Copolymer Having Acid-Labile Bicyclo Bisoxazolidine in the Side Chain for Controlled Release of Fragrance Aldehyde

A metharylate monomer having an octanal-derived bicyclo bisoxazolidine (BBOX) moiety was synthesized and was radically copolymerized with a methacrylate having a hydrophilic poly(ethylene glycol) chain to obtain an amphiphilic copolymer having the BBOX moieties as hydrophobic side chains. The BBOX moieties were stable for 7 days at pH 7.0, whereas they were gradually hydrolyze at pH 5.0 to release octanal continuously for 7 days, confirming the potential applicability of the copolymer to a polymeric pro-fragrance that can release aldehyde-type fragrance molecules slowly for a long period. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49:1881-1886, 2011

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Reference:
Oxazolidine – Wikipedia,
,Oxazolidine | C3H7NO – PubChem