Heterocyclic Building Blocks-piperidine

Voller, Jiri published the artcile6-Substituted purines as ROCK inhibitors with anti-metastatic activity, Safety of Piperidine-4-carboxamide, the publication is Bioorganic Chemistry (2019), 103005, database is CAplus and MEDLINE.

Rho-associated serine/threonine kinases (ROCKs) are principal regulators of the actin cytoskeleton that regulate the contractility, shape, motility, and invasion of cells. We explored the relationships between structure and anti-ROCK2 activity in a group of purine derivatives substituted at the C6 atom by piperidin-1-yl or azepan-1-yl groups. Structure-activity relationship (SAR) analyses suggested that anti-ROCK activity is retained, and may be further increased, by substitution of the parent compounds at the C2 atom or by expansion of the C6 side chain. These inhibitors of ROCK can reach effective concentrations within cells, as demonstrated by a decrease in phosphorylation of the ROCK target MLC, and by inhibition of the ROCK-dependent invasion of melanoma cells in the collagen matrix. Our study may be useful for further optimization of C6-substituted purine inhibitors of ROCKs and of other sensitive kinases identified by the screening of a broad panel of protein kinases.

Bioorganic 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 C15H14Cl2S2, Safety of Piperidine-4-carboxamide.

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

Kim, Ji Hyeon published the artcileIsomeric sp²-C-conjugated porous organic polymer-mediated photo- and sono-catalytic detoxification of sulfur mustard simulant under ambient conditions, Application of 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Matter (2021), 4(11), 3774-3785, database is CAplus.

The development of efficient strategies for the sustainable detoxification of mustard gas simulants has longstanding demand for human safety. Here, we present for the first time a photo- and sono-catalyzed selective detoxification of mustard gas simulants under ambient conditions using conveniently prepared porous organic polymer (POP) catalysts. We developed a microwave-assisted synthesis of three isomeric tetraphenylethylene-based POPs (TP_o, TP_m, and TP_p) bearing fully sp²-hybridized carbon frameworks. Among the three isomers, TPm efficiently generated ¹O₂, whereas TP_p generated both O^.-₂ and HO. under visible light irradiation, both TP_m and TP_p efficiently generated ROS to selectively convert 2-chloroethyl Et sulfide (CEES) into nontoxic 2-chloroethyl Et sulfoxide (CEESO) in the atm. conditions, through a known conversion mechanism. TP_mand TP_p can also generate ¹O₂ under ultrasound irradiation This work provides insight into designing new POP photo- and sono-catalysts to generate ROS in widespread applications.

Matter 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, Application of 2,2,6,6-Tetramethylpiperidin-4-one.

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

Campbell, Mark W. published the artcilePhotochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization, Category: piperidines, the publication is Journal of the American Chemical Society (2021), 143(10), 3901-3910, database is CAplus and MEDLINE.

Herein, the implementation of efficient, sustainable, diaryl ketone hydrogen-atom transfer (HAT) catalysis to activate native C-H bonds for multicomponent dicarbofunctionalization of alkenes was reported. The ability to forge new carbon-carbon bonds between reagents typically viewed as commodity solvents provided a new, more atom-economic outlook for organic synthesis. Through detailed exptl. and computational investigation, the critical effect of hydrogen bonding on the reactivity of this transformation was uncovered.

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, Category: piperidines.

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

Troast, Dawn M. published the artcileStudies toward the synthesis of (-)-zampanolide: preparation of the macrocyclic core, Quality Control of 219543-09-6, the publication is Advanced Synthesis & Catalysis (2008), 350(11+12), 1701-1711, database is CAplus and MEDLINE.

Studies towards the synthesis of the macrocyclic core of (-)-zampanolide (I) are reported. The synthetic approach features a one-pot reduction/vinylogous aldol reaction for construction of the C-15-C-20 fragment, an intramol. silyl-modified Sakurai (ISMS) reaction for construction of the 2,6-cis-disubstituted exo-methylene pyran subunit, and use of an sp²-sp³ Stille reaction for macrocyclization.

Advanced Synthesis & Catalysis 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 C18H34N4O5S, Quality Control of 219543-09-6.

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

Kang, Weilu published the artcileMarine colloids promote the adaptation of diatoms to nitrate contamination by directional electron transfer, Related Products of piperidines, the publication is Environmental Science & Technology (2022), 56(9), 5694-5705, database is CAplus and MEDLINE.

Nitrate contamination from human activities (e.g., domestic pollution, livestock breeding, and fertilizer application) threatens marine ecosystems and net primary productivity. As the main component of primary productivity, diatoms can adapt to high nitrate environments, but the mechanism is unclear. We found that electron transfer from marine colloids to diatoms enhances nitrogen uptake and assimilation under visible-light irradiation, providing a new pathway for nitrogen adaptation. Under irradiation, marine colloids exhibit semiconductor properties (e.g., the separation of electron-hole pairs) and can trigger the generation of free electrons and singlet oxygen. They also exhibit electron acceptor and donor properties, with the former being stronger than the latter, reacting with polysaccharides in extracellular polymeric substances (EPSs) under high nitrogen stress, enhancing the elasticity and permeability of cells, and promoting nitrogen assimilation and electron transfer to marine diatom EPSs. Electron transfer promotes extracellular-to-intracellular nitrate transport by upregulating membrane nitrate transporters and nitrate reductase. The upregulation of anion transport genes and unsaturated fatty acids contributes to nitrogen assimilation. We estimate that colloids may increase the nitrate uptake efficiency of marine diatoms by 10.5-82.2%. These findings reveal a mechanism by which diatoms adapt to nitrate contamination and indicate a low-cost strategy to control marine pollution.

Environmental Science & Technology 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, Related Products of piperidines.

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

Peng, Guilong published the artcileActivation of peroxymonosulfate by phosphite: Kinetics and mechanism for the removal of organic pollutants, Name: 2,2,6,6-Tetramethylpiperidin-4-one, the publication is Chemosphere (2021), 129016, database is CAplus and MEDLINE.

In this study, phosphite (HPO^2-₃) was used as a novel activator to activate peroxymonosulfate (PMS) for acid orange 7 (AO7) removal. Under the optimized conditions, the decolorization efficiency of AO7 was 82.1% within 60 min with rate constant values (k_obs) of 0.0301 min^-1. Besides, effects of the solution pH and the co-existing inorganic anions including Cl^–, HCO^–₃, HPO^2-₄ and SO^2-₄ on AO7 removal were also investigated. Except for SO^2-₄, other examined co-existing inorganic anions displayed favorable effects on the removal of AO7. Furthermore, the mechanism for PMS activation by the HPO^2-₃ was deeply elucidated by radical scavenger including ethanol (EtOH), tert-butanol (TBA), L-histidine and tiron, and ESR (ESR) studies. It was proposed that singlet oxygen (¹O₂) would be the dominant reactive oxygen species (ROS) in the HPO2-3/PMS system for contamination degradation at neutral pH condition. The findings of this study provided useful information for the application of the substances in industrial wastewaters to activate PMS for organic contaminants degradation and in particular for HPO^2-₃-rich electroplating wastewater treatment.

Chemosphere 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, Name: 2,2,6,6-Tetramethylpiperidin-4-one.

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

Crich, David published the artcileBenzylidene Acetal Fragmentation Route to 6-Deoxy Sugars: Direct Reductive Cleavage in the Presence of Ether Protecting Groups, Permitting the Efficient, Highly Stereocontrolled Synthesis of β-D-Rhamnosides from D-Mannosyl Glycosyl Donors. Total Synthesis of α-D-Gal-(1â†?)-α-D-Rha-(1â†?)-β-D-Rha-(1â†?)-β-D-Glu-OMe, the Repeating Unit of the Antigenic Lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652, Related Products of piperidines, the publication is Journal of the American Chemical Society (2004), 126(26), 8232-8236, database is CAplus and MEDLINE.

An approach to the stereocontrolled synthesis of β-D-rhamnopyranosides is described in which 2,3-O-benzyl or related 4,6-O-[α-(2-(2-iodophenyl)ethylthiocarbonyl)benzylidene]-mannosyl thioglycosides are first used to introduce the β-D-mannopyranoside linkage in high yield and stereoselectivity. Following glycosylation, treatment with tributyltin hydride in toluene at reflux brings about reductive radical fragmentation directly to the 6-deoxy sugar in high yield. A variation of these donors bearing a carboxylated donor on O3 is a highly α-selective mannosyl and, after radical fragmentation, α-D-rhamnosyl donor. Using this stereoselective glycosylation/radical-fragmentation approach, a concise synthesis of the title tetrasaccharide is realized in which both the β-D– and α-D-rhamnopyranosyl units are obtained in a single step by a double radical fragmentation of the modified benzylidene acetals.

Journal of the American Chemical Society 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, Related Products of piperidines.

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

Deng, Yongqi published the artcileDiscovery of liver-targeted inhibitors of stearoyl-CoA desaturase (SCD1), Computed Properties of 1032229-33-6, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(3), 791-796, database is CAplus and MEDLINE.

Inhibitors based on a benzo-fused spirocyclic oxazepine scaffold were discovered for stearoyl-CoA (CoA) desaturase 1 (SCD1) and subsequently optimized to potent compounds with favorable pharmacokinetic profiles and in vivo efficacy in reducing the desaturation index in a mouse model. Initial optimization revealed potency preferences for the oxazepine core and benzylic positions, while substituents on the piperidine portions were more tolerant and allowed for tuning of potency and PK properties. After preparation and testing of a range of functional groups on the piperidine nitrogen, three classes of analogs were identified with single digit nanomolar potency: glycine amides, heterocycle-linked amides, and thiazoles. Responding to concerns about target localization and potential mechanism-based side effects, an initial effort was also made to improve liver concentration in an available rat PK model. An advanced compound 17m with a 5-carboxy-2-thiazole substructure appended to the spirocyclic piperidine scaffold was developed which satisfied the in vitro and in vivo requirements for more detailed studies.

Bioorganic & Medicinal Chemistry Letters published new progress about 1032229-33-6. 1032229-33-6 belongs to piperidines, auxiliary class Metabolic Enzyme,SCD, name is 4-(2-Chlorophenoxy)-N-(3-(methylcarbamoyl)phenyl)piperidine-1-carboxamide, and the molecular formula is C20H22ClN3O3, Computed Properties of 1032229-33-6.

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

Qi, Jin-Chun published the artcileCDK13 upregulation-induced formation of the positive feedback loop among circCDK13, miR-212-5p/miR-449a and E2F5 contributes to prostate carcinogenesis, Application In Synthesis of 1702809-17-3, the publication is Journal of Experimental & Clinical Cancer Research (2021), 40(1), 2, database is CAplus and MEDLINE.

The expression levels of CDK13 in PCa tissues and different cell lines were determined by quant. real-time PCR and Western blot anal. In vitro and in vivo assays were preformed to explore the biol. effects of CDK13 in PCa cells. Furthermore, the mechanism of circCDK13 was investigated by using loss-of-function and gain-of-function assays in vitro and in vivo. Results: Here we show that CDK13 is significantly upregulated in human PCa tissues. CDK13 depletion and overexpression in PCa cells decrease and increase, resp., cell proliferation, and the pro-proliferation effect of CDK13 is strengthened by its interaction with E2F5. Mechanistically, transcriptional activation of endogenous CDK13, but not the forced expression of CDK13 by its expression vector, remarkably promotes E2F5 protein expression by facilitating circCDK13 formation. Further, the upregulation of E2F5 enhances CDK13 transcription and promotes circCDK13 biogenesis, which in turn sponges miR-212-5p/449a and thus relieves their repression of the E2F5 expression, subsequently leading to the upregulation of E2F5 expression and PCa cell proliferation. Conclusions: These findings suggest that CDK13 upregulation-induced formation of the pos. feedback loop among circCDK13, miR-212-5p/miR-449a and E2F5 is responsible for PCa development. Targeting this newly identified regulatory axis may provide therapeutic benefit against PCa progression and drug resistance.

Journal of Experimental & Clinical Cancer Research published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C30H32ClN7O2, Application In Synthesis of 1702809-17-3.

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

Geng, Meijuan published the artcileTargeting CDK12-mediated transcription regulation in anaplastic thyroid carcinoma, Safety of (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, the publication is Biochemical and Biophysical Research Communications (2019), 520(3), 544-550, database is CAplus and MEDLINE.

Anaplastic thyroid carcinoma (ATC) is the most aggressive type of thyroid cancer, with no effective treatment available. Identification of new anti-ATC drugs represents an urgent need. In this study, we find that ATC cells are highly sensitive to THZ531, a potent inhibitor of the transcriptional cyclin-dependent kinase (CDK), CDK12. Cell-based assays demonstrate that CDK12 inhibition significantly impedes cell cycle progression, induces apoptotic cell death, and impairs colony formation in ATC cells. THZ531 causes a loss of elongating RNA polymerase II and suppresses gene expression in ATC cells. An integrative anal. of gene expression profiles and super-enhancer landscape, combining with functional assays, leads to the discovery of two new ATC cancer genes, ZC3H4 and NEMP1. Furthermore, CDK12 inhibition enhances the sensitivity of ATC cells to doxorubicin-mediated chemotherapy. Thus, these findings indicate that CDK12 is a potential therapeutic target for ATC treatment and its inhibition may help to overcome the chemoresistance in patients with ATC.

Biochemical and Biophysical Research Communications published new progress about 1702809-17-3. 1702809-17-3 belongs to piperidines, auxiliary class Cell Cycle,CDK, name is (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide, and the molecular formula is C30H32ClN7O2, Safety of (R,E)-N-(4-(3-((5-Chloro-4-(1H-indol-3-yl)pyrimidin-2-yl)amino)piperidine-1-carbonyl)phenyl)-4-(dimethylamino)but-2-enamide.

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