Heterocyclic Building Blocks-piperidine

Goto, Kenta published the artcileThe Total Synthesis of Starfish Ganglioside GP3 Bearing a Unique Sialyl Glycan Architecture, COA of Formula: C11H15NOS, the publication is Chemistry – A European Journal (2016), 22(24), 8323-8331, database is CAplus and MEDLINE.

The total synthesis of ganglioside GP3, which is found in the starfish Asterina pectinifera, has been accomplished through stereoselective and effective glycosylation reactions. The sialic acid embedded octasaccharide moiety of the target compound was constructed by [4+4] convergent coupling. A tetrasaccharyl donor and acceptor that contained internal sialic acid residues were synthesized with an orthogonally protected N-Troc sialic acid donor as the key common synthetic unit, and they underwent highly stereoselective glycosidation. The resulting sialosides were subsequently transformed into reactive glycosyl acceptors. [4+4] coupling furnished the octasaccharide framework in 91 % yield as a single stereoisomer. Final conjugation of the octasaccharyl donor and glucosyl ceramide acceptor produced the protected target compound in high yield, which underwent global deprotection to successfully deliver ganglioside GP3.

Chemistry – A European Journal published new progress about 4972-31-0. 4972-31-0 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-(Phenylsulfinyl)piperidine, and the molecular formula is C11H15NOS, COA of Formula: C11H15NOS.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Gaonkar, Supreet published the artcileExploring the potential of newly synthesized 4-methyl-6-morpholino-pyrimidine derivatives as antiproliferative agents, Recommanded Product: Piperidine-4-carboxamide, the publication is New Journal of Chemistry (2018), 42(4), 2790-2803, database is CAplus.

In view of exploring the potential of pyrimidine derivatives as anticancer agents, a series of 4-methyl-6-morpholinopyrimidine derivatives was synthesized and characterised by NMR (¹H & ¹³C), SC-XRD and mass spectral anal. The in vitro anticancer activity of these compounds was investigated using different human cancer cell lines, namely HeLa (cervix), NCI-H460 (lung), MCF-7 (breast), HepG2 (liver) and IMR-32 (brain). Compounds 4c and 5h exhibited potent anticancer activity in a dose-dependent manner as compared to other derivatives, with IC₅₀ values of 5.88 ± 1.22 and 6.11 ± 2.12 μM on HeLa and NCI-H460, cells resp. The inhibitory effect of 4c and 5h on cancer cell proliferation was shown to be a consequence of reactive oxygen species (ROS) generation and subsequent induction of cellular apoptosis, as evidenced by an increase in hypodiploid (subG1) population, early apoptotic cell population, caspase-3/7 activity, loss of mitochondrial membrane potential and degradation of nuclear DNA. Furthermore, mol. docking studies revealed that 4c and 5h compounds bind to the ATP binding pocket of the mammalian target of rapamycin (mTOR). Based on our results, we conclude that 4-methyl-6-morpholinopyrimidine derivatives prevent cancer cell proliferation by inducing apoptosis and thus have potential to be further explored for anticancer properties.

New Journal of Chemistry published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Recommanded Product: Piperidine-4-carboxamide.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Vilar, Santiago published the artcileProbabilistic Neural Network Model for the In Silico Evaluation of Anti-HIV Activity and Mechanism of Action, COA of Formula: C7H15NO, the publication is Journal of Medicinal Chemistry (2006), 49(3), 1118-1124, database is CAplus and MEDLINE.

A theor. model has been developed that discriminates between active and nonactive drugs against HIV-1 with four different mechanisms of action for the active drugs. The model was built up using a probabilistic neural network (PNN) algorithm and a database of 2720 compounds The model showed an overall accuracy of 97.34% in the training series, 85.12% in the selection series, and 84.78% in an external prediction series. The model not only correctly classified a very heterogeneous series of organic compounds but also discriminated between very similar active/nonactive chems. that belong to the same family of compounds More specifically, the model recognized 96.02% of nonactive compounds, 94.24% of active compounds that inhibited reverse transcriptase, 97.24% of protease inhibitors, 97.14% of virus uncoating inhibitors, and 90.32% of integrase inhibitors. The results indicate that this approach may represent a powerful tool for modeling large databases in QSAR with applications in medicinal chem.

Journal of Medicinal Chemistry published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C16H14O6, COA of Formula: C7H15NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Lackner, Aaron D. published the artcileSingle-Operation Deracemization of 3H-Indolines and Tetrahydroquinolines Enabled by Phase Separation, Application In Synthesis of 219543-09-6, the publication is Journal of the American Chemical Society (2013), 135(38), 14090-14093, database is CAplus and MEDLINE.

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asym. redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

Journal of the American Chemical Society published new progress about 219543-09-6. 219543-09-6 belongs to piperidines, auxiliary class Piperidine,Fluoride,Salt,Amine,Amide, name is 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate, and the molecular formula is C11H21BF4N2O2, Application In Synthesis of 219543-09-6.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Dileep, K. V. published the artcilePiperidine-4-carboxamide as a new scaffold for designing secretory glutaminyl cyclase inhibitors, Application In Synthesis of 39546-32-2, the publication is International Journal of Biological Macromolecules (2021), 415-423, database is CAplus and MEDLINE.

Alzheimer’s disease (AD), a common chronic neurodegenerative disease, has become a major public health concern. Despite years of research, therapeutics for AD are limited. Overexpression of secretory glutaminyl cyclase (sQC) in AD brain leads to the formation of a highly neurotoxic pyroglutamate variant of amyloid beta, pGlu-Aβ, which acts as a potential seed for the aggregation of full length Aβ. Preventing the formation of pGlu-Aβ through inhibition of sQC has become an attractive disease-modifying therapy in AD. In this current study, through a pharmacophore assisted high throughput virtual screening, we report a novel sQC inhibitor (Cpd-41) with a piperidine-4-carboxamide moiety (IC₅₀ = 34μM). Systematic mol. docking, MD simulations and X-ray crystallog. anal. provided atomistic details of the binding of Cpd-41 in the active site of sQC. The unique mode of binding and moderate toxicity of Cpd-41 make this mol. an attractive candidate for designing high affinity sQC inhibitors.

International Journal of Biological Macromolecules published new progress about 39546-32-2. 39546-32-2 belongs to piperidines, auxiliary class Piperidine,Amine,Amide, name is Piperidine-4-carboxamide, and the molecular formula is C6H12N2O, Application In Synthesis of 39546-32-2.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Wan, Wen-jing published the artcileImprovement of 2,2,6,6-tetramethyl-4-piperidinamine synthesis via catalytic amination, Product Details of C9H17NO, the publication is Gaoxiao Huaxue Gongcheng Xuebao (2020), 34(2), 457-462, database is CAplus.

2,2,6,6-Tetramethylpiperidinamine as light stabilizer of hindered amines was synthesized via catalytic amination of 2,2,6,6-tetramethylpiperidone. Imine formation was promoted by adjusting reaction system pH, which facilitated the catalytic amination under mild condition. The selectivity of the product was increased. When studied under pH∼12.5, reaction temperature 60°C and pressure 2 MPa, the selectivity of TEMP was up to 95.2%. The result shows that pH=12.5 is the most favorable condition for the formation of TEMP.

Gaoxiao Huaxue Gongcheng Xuebao published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C20H18BrN3, Product Details of C9H17NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Carocci, Alessia published the artcileSynthesis and Evaluation of Voltage-Gated Sodium Channel Blocking Pyrroline Derivatives Endowed with Both Antiarrhythmic and Antioxidant Activities, Formula: C9H17NO, the publication is ChemMedChem (2021), 16(3), 578-588, database is CAplus and MEDLINE.

Under the hypothesis that cardioprotective agents might benefit from synergism between antiarrhythmic activity and antioxidant properties, a small series of mexiletine analogs were coupled with the 2,2,5,5-tetramethylpyrroline moiety, known for its antioxidant effect, in order to obtain dual-acting drugs potentially useful in the protection of the heart against post-ischemic reperfusion injury. The pyrroline derivatives reported herein were found to be more potent as antiarrhythmic agents than mexiletine and displayed antioxidant activity. The most interesting tetramethylpyrroline congener, a tert-butyl-substituted analog, was at least 100 times more active as an antiarrhythmic than mexiletine.

ChemMedChem published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, Formula: C9H17NO.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Frawley, Thomas F. published the artcileAdrenal cortical function during isoniazid therapy for pulmonary tuberculosis, Application of 1-Ethylpiperidin-3-ol, the publication is American Review of Tuberculosis (1954), 841-51, database is CAplus.

The nature of the host’s response during isoniazid therapy for pulmonary tuberculosis suggested a possible adrenal cortical influence. By utilizing eosinophil levels, 17-keto steroid, uric acid, creatinine, and 17-hydroxy corticoid excretion patterns, the level of adrenal activity was determined before and during isoniazid therapy. Adrenal cortical responsiveness was assessed by the 8-hr. intravenous corticotropin test both before and during therapy. In no instance in either the resting or stimulated state was a significant or consistent deviation from the normal observed. A gradual rise in circulating eosinophils occurred during isoniazid therapy. The urinary uric acid-creatinine ratio varied directly with the disease progress and further use of this as an index of degree of disease activity is suggested.

American Review of Tuberculosis published new progress about 13444-24-1. 13444-24-1 belongs to piperidines, auxiliary class Piperidine,Alcohol, name is 1-Ethylpiperidin-3-ol, and the molecular formula is C7H15NO, Application of 1-Ethylpiperidin-3-ol.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Knutson, Daniel E. published the artcileImproved scale-up synthesis and purification of clinical asthma candidate MIDD0301, Formula: C19H21N, the publication is Organic Process Research & Development (2020), 24(8), 1467-1476, database is CAplus and MEDLINE.

An improved and scalable synthesis of MIDD0301, a pos. GABAA receptor modulator that is under development as oral and inhaled treatments for asthma was reported. The starting material to generate MIDD0301 is 2-amino-5-bromo-2′-fluorobenzophenone, which has a non-basic nitrogen due to electron withdrawing substituents in ortho and para positions, reducing its reactivity towards activated carboxylic acids. Investigations of peptide coupling reagents on multigram scale resulted in moderate yields due to incomplete conversions. Secondly, basic conditions used for the formation of the seven-member 1,4-diazepine ring resulted in racemization of the chiral center. It was found that neutral conditions comparable to the pKa of the primary amine where sufficient to support the formation of the intramol. imine but did not enable the simultaneous removal of the protecting group. Both difficulties were overcome with the application of the N-carboxyanhydride of D-alanine. Activated in the presence of acid, this compound reacted with non-basic 2-amino-5-bromo-2′-fluorobenzophenone and formed the 1,4-diazepine upon neutralization with triethylamine. Carefully designed workup procedures and divergent solubility of the synthesis intermediates in solvents and solvent combinations were utilized to eliminate the need for column chromatog. To improve compatibility with large scale reactors, temperature-controlled slow addition of reagents generated the imidazodiazepine at -20°C. All intermediates were isolated with a purity of >97% and impurities were identified and quantified. After the final hydrolysis step, MIDD0301 was isolated with a 44% overall yield and purity of 98.9% after recrystallization The enantiomeric excess was higher than 99.0%.

Organic Process Research & Development published new progress about 35661-58-6. 35661-58-6 belongs to piperidines, auxiliary class Piperidine,Benzene, name is 1-((9H-Fluoren-9-yl)methyl)piperidine, and the molecular formula is C19H21N, Formula: C19H21N.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem

Ren, Zhongfei published the artcileIbuprofen degradation using a Co-doped carbon matrix derived from peat as a peroxymonosulphate activator, HPLC of Formula: 826-36-8, the publication is Environmental Research (2021), 110564, database is CAplus and MEDLINE.

The wider presence of pharmaceuticals and personal care products in nature is a major cause for concern in society. Among pharmaceuticals, the anti-inflammatory drug ibuprofen has commonly been found in aquatic and soil environments. We produced a Co-doped carbon matrix (Co-P 850) through the carbonization of Co²⁺ saturated peat and used it as a peroxymonosulfate activator to aid ibuprofen degradation The properties of Co-P 850 were analyzed using field emission SEM, energy filtered transmission electron microscopy and XPS. The characterization results showed that Co/Fe oxides were generated and tightly embedded into the carbon matrix after carbonization. The degradation results indicated that high temperature and slightly acidic to neutral conditions (pH = 5 to 7.5) promoted ibuprofen degradation efficiency in the Co-P 850/peroxymonosulfate system. Anal. showed that approx. 52% and 75% of the dissolved organic carbon was removed after 2 h and 5 h of reaction time, resp. Furthermore, the existence of chloride and bicarbonate had adverse effects on the degradation of ibuprofen. Quenching experiments and ESR anal. confirmed that SO·-4, ·OH and O ·^-2 radicals together contributed to the high ibuprofen degradation efficiency. In addition, we identified 13 degradation intermediate compounds and an ibuprofen degradation pathway by mass spectrometry anal. and quantum computing. Based on the results and methods presented in this study, we propose a novel way for the synthesis of a Co-doped catalyst from spent NaOH-treated peat and the efficient catalytic degradation of ibuprofen from contaminated water.

Environmental Research published new progress about 826-36-8. 826-36-8 belongs to piperidines, auxiliary class Natural product, name is 2,2,6,6-Tetramethylpiperidin-4-one, and the molecular formula is C9H17NO, HPLC of Formula: 826-36-8.

Referemce:
https://en.wikipedia.org/wiki/Piperidine,
Piperidine | C5H11N – PubChem