Category: piperidines

Huang, Wanrong published the artcileSubstituted 2-thioxothiazolidin-4-one derivatives showed protective effects against diabetic cataract via inhibition of aldose reductase, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is thioxo thiazolidinone derivative preparation aldose reductase inhibitor diabetic cataract; aldose reductase; cataract; docking; synthesis.

In an effort to develop a new class of potent aldose reductase inhibitors against diabetic cataracts, a series of novel 2-thioxothiazolidine-4-one derivatives was synthesized in excellent yields via a facile synthetic route. These compounds were tested against aldehyde (ALR1) and aldose reductase (ALR2) enzymes, where they showed considerable inhibitory activity. Among the tested derivatives, compound 6e showed selective and excellent inhibition of ALR2 over ALR1. The exptl. diabetes was induced by the i.p. administration of streptozotocin in male Wistar rats. Compound 6e showed pos. modulation of body weight, blood glucose, and blood insulin levels in diabetic rats. Compound 6e also showed ALR2 inhibition as evidenced by Western blot anal. in lens homogenates of Wistar rats having cataract. The docking study of 6e was also performed inside the active site of ALR2 to enumerate the key contacts for inhibitory activity.

Archiv der Pharmazie (Weinheim, Germany) published new progress about Aldose reductase inhibitors. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Vojkovsky, Tomas published the artcileDetection of secondary amines on solid phase, Recommanded Product: 1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid, the main research area is Merrifield synthesis chloranil monitoring; amine secondary detection Merrifield synthesis.

The detection of secondary amino groups in building blocks attached to solid phase using tetrachlorobenzoquinone (chloranil) was re-examined A new procedure, about ten times more sensitive than the original method, has been developed. Except for N-p-tolylglycine, all secondary amino groups that were examined were detected reliably in a substitution range down to 2.8 μeq/g. Protected imidazole in His(Trt) did not interfere with the detection method.

Peptide Research published new progress about Solid phase synthesis, solid-phase peptide synthesis. 158922-07-7 belongs to class piperidines, name is 1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid, and the molecular formula is C21H21NO4, Recommanded Product: 1-(((9H-Fluoren-9-yl)methoxy)carbonyl)piperidine-3-carboxylic acid.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Masuda, Arisa published the artcileN1-Substituted benzimidazole scaffold for farnesoid X receptor (FXR) agonists accompanying prominent selectivity against vitamin D receptor (VDR), Category: piperidines, the main research area is benzimidazole derivative preparation farnesoid vitamin D receptor osteoblast differentiation; Benzimidazole; FXR agonist; Osteoblast differentiation.

As a cellular bile acid sensor, farnesoid X receptor (FXR) participates in regulation of bile acid, lipid and glucose homeostasis, and liver protection. With respect to the bone metabolism, FXR pos. regulates bone metabolism through both bone formation and resorption of the bone remodeling pathways. Some of FXR agonists possessing isoxazole moiety are undergoing clin. trials for the treatment of non-alc. steatohepatitis. To date, therefore, the activation of FXR leads to considerable interest in FXR as potential therapeutic targets. We have identified a series of nonsteroidal FXR agonists bearing N1-Me benzimidazole and isoxazole moieties that are bridged with aromatic derivatives They showed affinity to FXR, but also weak affinity toward the vitamin D receptor (VDR) that involves regulation of calcium and phosphate homeostasis and is activated by bile acids. The deployment of FXR agonists without activity against VDR as off-target is therefore crucial in the development of FXR ligands. Our efforts focusing on increasing the agonist properties towards FXR led to the discovery of 19, which activates FXR at and below nanomolar levels (EC50 = 26.5 ± 10.5 nM TR-FRET and 0.8 ± 0.2 nM luciferase, resp.) and functions as a FXR agonist: the affinity toward FXR over eight nuclear receptors, including VDR [IC50 (VDR) / EC50 (FXR) > 5000] and TGR5, effects FXR target genes, and activates bone morphogenetic protein-2-induced differentiation of mouse bone marrow-derived mesenchymal stem cell-like ST2 cells into osteoblast.

Bioorganic & Medicinal Chemistry published new progress about Bone marrow (-derived mesenchymal stem cell). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Category: piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Gao, Ping published the artcileNovel indolylarylsulfone derivatives as covalent HIV-1 reverse transcriptase inhibitors specifically targeting the drug-resistant mutant Y181C, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is human immunodeficiency virus 1 indolylarylsulfone cysteine phenylalanine proline; Covalent inhibitor; HIV-1; Indolylarylsulfones; NNRTIs; Y181C.

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are widely used in combination therapies against HIV-1. However, emergent and transmitted drug resistance compromise their efficacy in the clin. setting. Y181C is selected in patients receiving nevirapine, etravirine and rilpivirine, and together with K103N is the most prevalent NNRTI-associated mutation in HIV-infected patients. Herein, we report on the design, synthesis and biol. evaluation of a novel series of indolylarylsulfones bearing acrylamide or ethylene sulfonamide reactive groups as warheads to inactivate Cys181-containing HIV-1 RT via a Michael addition reaction. Compounds I-7 and I-9 demonstrated higher selectivity towards the Y181C mutant than against the wild-type RT, in nucleotide incorporation inhibition assays. The larger size of the NNRTI binding pocket in the mutant enzyme facilitates a better fit for the active compounds, while stacking interactions with Phe227 and Pro236 contribute to inhibitor binding. Mass spectrometry data were consistent with the covalent modification of the RT, although off-target reactivity constitutes a major limitation for further development of the described inhibitors.

Bioorganic & Medicinal Chemistry published new progress about Antiviral agent resistance (drug-resistant). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yamaki, Susumu published the artcileSynthesis and pharmacological evaluation of glycine amide derivatives as novel vascular adhesion protein-1 inhibitors without CYP3A4 and CYP2C19 inhibition, HPLC of Formula: 887425-47-0, the main research area is glycine amide derivative preparation vascular adhesion protein VAP1 inhibitor; diabetic nephropathy treatment glycine amide derivative VAP1 inhibitor; CYP2C19; CYP3A4; Diabetic nephropathy; Glycine amide; Vascular adhesion protein-1.

Vascular adhesion protein-1 (VAP-1) is a promising therapeutic target for the treatment of diabetic nephropathy. Here, the authors conducted optimization studies of the authors’ lead compound 1 (I), which the authors previously reported as a novel VAP-1 inhibitor, to enhance the inhibition of human VAP-1 and to reduce CYP3A4 and CYP2C19 inhibition. As a result, the authors identified 3-chloro-4-{4-[5-(3-{[glycyl(methyl)amino]methyl}phenyl)pyrimidin-2-yl]piperazin-1-yl}benzoic acid (17h) as a novel orally active VAP-1 inhibitor, with 14-fold increased human VAP-1 inhibitory activity compared to 1, without CYP3A4 and CYP2C19 inhibition. Oral administration of 17h significantly inhibited the progression of proteinuria in streptozotocin (STZ) induced diabetic rats at 0.3 and 1 mg/kg, suggesting that this compound has potential to be a therapeutic agent for the treatment of diabetic nephropathy.

Bioorganic & Medicinal Chemistry published new progress about Bioactive lead compounds (optimization). 887425-47-0 belongs to class piperidines, name is 1-(5-Bromopyrimidin-2-yl)piperidin-4-ol, and the molecular formula is C9H12BrN3O, HPLC of Formula: 887425-47-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Anil Kumar, K. S. published the artcileSynthesis and identification of chiral (aminomethyl)piperidine carboxamides as inhibitor of collagen induced platelet activation, Synthetic Route of 132431-09-5, the main research area is antithrombotic anticoagulant; Aminomethylpiperidine; Antiplatelet; Collagen; Epinephrine; Pyroglutamic acid; Thrombosis.

Several chiral lactam carboxamides of (aminomethyl)piperidine were synthesized and investigated for a collagen induced in vitro anti-platelet efficacy and collagen plus epinephrine induced in vivo pulmonary thromboembolism. One compound (30 μM/kg) displayed a remarkable antithrombotic efficacy (60% protection) which was sustained for more than 24 h and points to its excellent bioavailability. Other compounds (IC50 = 6.6 μM, IC50 = 37 μM), as well as their racemic mixture (IC50 = 16 μM) significantly inhibited collagen-induced human platelet aggregation in vitro. One compound displayed a dual mechanism of action against both collagen (IC50 = 3.3 μM) and (5Z)-7-[(1R,4S,5S,6R)-6-[(1E,3S)-3-hydroxy-1-octen-1-yl]-2-oxabicyclo[2.2.1]heptyl]-4-heptenoic acid (U46619) (IC50 = 2.7 μM) induced platelet aggregation. A pharmacokinetic study indicated faster absorption, prolonged and constant systemic exposure and thereby exhibiting better therapeutic response. The synthesis of the target compounds was achieved using 5-oxo-L-proline esters (pyroglutamic acid esters) and analogs, such as 2-oxo-4-oxazolidinecarboxylic acid ester, 2-oxo-4-thiazolidinecarboxylic acid ester, (2S)-6-oxo-2-piperidinecarboxylic acid ester and morpholine analogs as reactants. The title compounds thus formed included N-[[(3S)-1-[[(2S)-1-[(4-methylphenyl)methyl]-5-oxo-2-pyrrolidinyl]carbonyl]-3-piperidinyl]methyl]carbamic acid ester and related substances, such as an epimer N-[[(3R)-1-[[(2S)-1-[(4-methylphenyl)methyl]-5-oxo-2-pyrrolidinyl]carbonyl]-3-piperidinyl]methyl]carbamic acid ester and related substances..

European Journal of Medicinal Chemistry published new progress about Anticoagulants (antithrombotic agents). 132431-09-5 belongs to class piperidines, name is Benzyl (piperidin-4-ylmethyl)carbamate, and the molecular formula is C14H20N2O2, Synthetic Route of 132431-09-5.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Dou, Zhe published the artcileKinetic resolution of nearly sym. 3-cyclohexene-1-carboxylate esters using a bacterial carboxylesterase identified by genome mining, Synthetic Route of 1690-74-0, the main research area is kinetic resolution carboxyesterase enzymic hydrolysis.

A new bacterial carboxylesterase (CarEst3) was identified by genome mining and found to efficiently hydrolyze racemic Me 3-cyclohexene-1-carboxylate (rac-CHCM) with a nearly sym. structure for the synthesis of (S)-CHCM. CarEst3 displayed a high substrate tolerance and a stable catalytic performance. The enantioselective hydrolysis of 4.0 M (560 g·L-1) rac-CHCM was accomplished, yielding (S)-CHCM with a >99% ee, a substrate to catalyst ratio of 1400 g·g-1, and a space-time yield of 538 g·L-1·d-1.

Organic Letters published new progress about Enantioselective biochemical synthesis. 1690-74-0 belongs to class piperidines, name is Methyl 1-methylpiperidine-2-carboxylate, and the molecular formula is C8H15NO2, Synthetic Route of 1690-74-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Wanner, Benedikt published the artcileCatalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights, Application of 1-N-Boc-2-Ethylpiperidin-4-one, the main research area is piperidine nonracemic preparation; kinetic resolution piperidine acylation nonracemic indanooxazinol hydrocinnamate; dependence acylation enantioselectivity stereochem disubstituted piperidine; transition state model enantioselective acylation piperidine nonracemic indanooxazinol hydrocinnamate; nitrophenylsulfonyl benzylethylpiperidine mol crystal structure.

Resolution of 2,3-, 2,4-, and 2,5-disubstituted piperidines using either a nonracemic hydroxamate ester I (R = 4-MeOC6H4) or using an unsaturated α-hydroxy-α’,β’-unsaturated ketone in the presence of a nonracemic hydroxamate and a pyrrolotriazolium N-heterocyclic carbene precursor yielded N-acylated piperidines and nonracemic piperidines with practical selectivity factors (s, up to 52). The selectivity of resolution depended strongly on the conformation of the piperidine reactants, with cis-2,3- and 2,5-disubstituted piperidines and trans-2,4-disubstituted piperidines being resolved more effectively than trans-2,3- and 2,5-disubstituted and cis-2,4-disubstituted piperidines. The method was also used for the resolution of 2-substituted 4-methylenepiperidines and 2-substituted 4-piperidinone ethylene and propylene ketals. Detailed exptl. and computational studies of the kinetic resolution of various disubstituted piperidines revealed a strong preference for the acylation of conformers in which the α-substituent occupies the axial position. This work provides further exptl. and computational support for the concerted 7-membered transition state model for acyl transfer reagents and expands the scope and functional group tolerance of the secondary amine kinetic resolution The structure of a nonracemic (nitrophenylsulfonyl)benzylethylpiperidine was determined by X-ray crystallog.

Journal of the American Chemical Society published new progress about Acylation catalysts (stereoselective). 324769-07-5 belongs to class piperidines, name is 1-N-Boc-2-Ethylpiperidin-4-one, and the molecular formula is C12H21NO3, Application of 1-N-Boc-2-Ethylpiperidin-4-one.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chang, Chia-Wei published the artcileThe effects of adding different HALS on the curing process, film properties and lightfastness of refined oriental lacquer, Related Products of piperidines, the main research area is hindered amine stabilizer curing lightfastness oriental lacquer film property; hindered amine light stabilizers; laccase-catalyzed reaction; oriental lacquer; oxidative polymerization.

Oriental lacquer is a natural polymeric coating with a satiny texture and excellent characteristics, such as chem. resistance and durability. However, the poor lightfastness resulted in the natural aromatic structures of the urushiol structures limited its suitability for outdoor application. This study aimed at the improvement of the lightfastness by adding the different hindered amine light stabilizers (HALS) with 2 phr addition as well as the effects on the coating and film property of the refined oriental lacquers (RL). The Cryptomeria japonica plate, glass sheets, and the other substrates were used for finishing. The results showed that the lightfastness of RL film was obviously improved by adding 2 phr HALS of Bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate (H90) containing -NH group and Bis (1,2,2,6,6-pentamethyl-4-piperidinyl)-[[3,5-bis(1,1-di-Me ethyl) -4-hydroxyphenyl] methyl] butylmalonate (H60) containing -NCH3 groups. The HALS additions increased the pH value of RL and improved the activities of laccase-catalyzed reaction. Meanwhile, the oxidative polymerization of the side chains of RL was inhibited, caused by a radical scavenging ability of HALS. The changes in the drying process affected not only the curing time, but also the film properties. Among the 2 phr additions of different HALS, the film containing H90 had the best lightfastness. Meanwhile, it kept the most similar properties with RL and shortened the drying time of RL, and it was selected as the best HALS addition under 2 phr in this study.

Polymers (Basel, Switzerland) published new progress about Abrasion-resistant coating materials. 52829-07-9 belongs to class piperidines, name is Bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate, and the molecular formula is C28H52N2O4, Related Products of piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Kang, Qi-Kai published the artcileRu(II)-Catalyzed Amination of Aryl Fluorides via η6-Coordination, Related Products of piperidines, the main research area is fluorobenzene amine diphenyl phosphane ruthenium catalyst regioselective amination; aminobenzene preparation.

A Ru/hemilabile-ligand catalyzed nucleophilic aromatic substitution (SNAr) of aryl fluorides as the limiting reagents was developed. Significant ligand enhancement was demonstrated by the engagement of both electron-rich and neutral arenes in the SNAr amination without using excess arenes. Preliminary mechanistic studies revealed that the nucleophilic substitution proceeds on a η6-complex of the Ru-catalyst and the substrate, and the hemilabile ligand facilitated dissociation of products from the metal center.

Journal of the American Chemical Society published new progress about Amination catalysts (regioselective). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Related Products of piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem