09/9/2021 News Archives for Chemistry Experiments of C5H7NO2

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Nitrogen heterocycles are ubiquitous in natural products and pharmaceuticals. Herein, we disclose a nitrogen complexation strategy that employs a strong Bronsted acid (HBF4) or an azaphilic Lewis acid (BF3) to enable remote, non-directed C(sp3)-H oxidations of tertiary, secondary, and primary amine- and pyridine-containing molecules with tunable iron catalysts. Imides resist oxidation and promote remote functionalization.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H1372N – PubChem

 

09/9/2021 News Archives for Chemistry Experiments of C5H7NO2

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Deamidation is a major fragmentation channel upon activation by collision induced dissociation (CID) for protonated peptides containing glutamine (Gln) and asparagine (Asn) residues. Here, we investigate these NH3-loss reactions for four Asn- and Gln-containing protonated peptides in terms of the resulting product ion structures using infrared ion spectroscopy with the free electron laser FELIX. The influence of the side chain length (Asn versus Gln) and of the amino acid sequence on the deamidation reaction has been examined. Molecular structures for the product ions are determined by comparison of experimental IR spectra with spectra predicted by density functional theory (DFT). The reaction mechanisms identified for the four dipeptides AlaAsn, AsnAla, AlaGln, and GlnAla are not the same. For all four dipeptides, primary deamidation takes place from the amide side chain (and not from the N-terminus) and, in most cases, resembles the mechanisms previously identified for the protonated amino acids asparagine and glutamine. Secondary fragmentation reactions of the deamidation products have also been characterized and provide further insight in ? and confirmation of ? the identified mechanisms. Overall, this study provides a comprehensive molecular structure map of the deamidation chemistry of this series of dipeptides. [Figure not available: see fulltext.]

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H1449N – PubChem

 

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The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H1287N – PubChem

 

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In this study, novel imidazo[2,1-b][1,3,4]thiadiazole (ITD) compounds were synthesized and their antimicrobial and antioxidant capacity was examined. The C-2 position of the ITD structure was fixed with the 3,4-hydroxybenzene ring and the properties of the two series of compounds obtained by phenyl or 4-chlorophenyl in the C-6 position were compared. In the formation of these series, new properties were determined by the addition of different pharmacophore to the target product by binding of the groups known in the literature from the C-5 position to the structure. In the study, it was seen that the compounds 4a, 4b, 5a, 5b, 7f, 10, 12 and 13 had very high anti-tuberculosis activities at low concentrations, 3b was found to exhibit moderate activity while other synthesis compounds exhibited moderate activity. In addition, it showed activity against gram positive and negative bacteria. In the determination of the antioxidant capacities of the newly synthesized compounds by FRAP and DPPH methods, the compounds showing activity were found to be 2, 3a, 3b, 6c, 9, 11 and 13. The structures of all synthesized compounds were solved by spectroscopic methods such as FT-IR, 1H NMR, 13C NMR and mass.

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Piperidine – Wikipedia,
Piperidine | C5H1405N – PubChem

 

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A series of trans- and cis-3,4-disubstituted 5-oxomorpholine-2-carboxylic acids 5 were prepared by a cyclocondensation between diglycolic anhydride 3 and arylideneamines 4. Transformations of the carboxylic group leading to a peptide bond in the side chain to the morpholinone ring were effected. The relative configurations and the preferred conformations of the substituents at the morpholinone ring in some of the newly prepared derivatives were determined by means of 1H NMR and X-ray analysis.

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Piperidine – Wikipedia,
Piperidine | C5H1516N – PubChem

 

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Intramolecular amidocyclopropanation reactions of diethoxymethyl-lactams containing a pendant alkene were examined using zinc/TMSCl. With a range of 4-6-membered lactams, bicyclic amidocyclopropanes were obtained with very high diastereoselectivity with a preference for the formation of the more hindered endo-cyclopropane.

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Piperidine – Wikipedia,
Piperidine | C5H1400N – PubChem

 

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A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.

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Piperidine – Wikipedia,
Piperidine | C5H1540N – PubChem

 

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Preparation and affinity to 5-HT1A and 5-HT2A receptors of new buspirone analogues 7-17 are reported. The compounds possess high to low affinity to 5-HT1A and moderate to low to 5-HT2A receptors. The crystal structures have been determined for compounds 11, 12, 13, and 14. For low affinity ligand (15) of 5-HT1A receptor conformational analysis was performed and compared with similar analyses performed for know high (buspirone 1) and very high (WY-48,723 2) affinity ligands of the receptor. Structure-activity relationship is discussed for the affinity to 5-HT1A receptor. A three-point pharmacophore explaining interactions of buspirone-like molecules with the receptor binding site is proposed.

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Piperidine – Wikipedia,
Piperidine | C5H1361N – PubChem

 

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matrix presented The synthesis of (-)-epibatidine has been accomplished utilizing a highly exo-selective asymmetric hetero Diels-Alder reaction. The key steps employed to transform the resulting bicycle into the natural product include a fluoride-promoted fragmentation and a Hofmann rearrangement.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H1390N – PubChem

 

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A series of 2-(2-nitrobenzoyl)cyclohexane-1,3-dione analogues (1 -9) were designed, synthesized, and evaluated for inhibition of 4-hydroxyphenylpyruvate dioxygenase (4-HPPD), a key enzyme involved in the catabolism of tyrosine which catalyzes the conversion of 4-hydroxyphenylpyruvate to homogentisate. The correlations between the results of enzyme inhibition, ferric chloride tests, and the conformational analysis suggested that the tight binding between triketonetype inhibitors and 4-HPPD is likely due to chelation of the enzyme-bound ferric iron with the enol tautomer of 1,3-diketone moiety of the triketones. The presence of a 2-carbonyl group in the triketone is an essential structural feature for potent 4-HPPD inhibition. Modification of the 3-carbonyl group of triketone moiety to other functionality will reduce the overall planarity and thus prevent keto-enol tautomerization, resulting in a decrease or lack of inhibition activity.

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Reference:
Piperidine – Wikipedia,
Piperidine | C5H1523N – PubChem