Month: November 2022

Rahimi, Alireza published the artcileChemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin, Quality Control of 219543-09-6, the publication is Journal of the American Chemical Society (2013), 135(17), 6415-6418, database is CAplus and MEDLINE.

An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcs. within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO₃ and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.

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, Quality Control of 219543-09-6.

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

Cogan, D. A. published the artcileStructure-based design and subsequent optimization of 2-tolyl-(1,2,3-triazol-1-yl-4-carboxamide) inhibitors of p38 MAP kinase, Safety of (1-Methylpiperidin-3-yl)methanamine, the publication is Bioorganic & Medicinal Chemistry Letters (2008), 18(11), 3251-3255, database is CAplus and MEDLINE.

A computer-aided drug design strategy leads to the identification of a new class of p38 inhibitors based on the 2-tolyl-(1,2,3-triazol-1-yl-4-carboxamide) scaffold. The tolyl triazole amides provided a potent platform amenable to optimization. Further exploration leads to compounds with greater than 100-fold improvement in binding affinity to p38. Derivatives prepared to alter the physicochem. properties produced inhibitors with IC₅₀‘s in human whole blood as low as 83 nM.

Bioorganic & Medicinal Chemistry Letters published new progress about 14613-37-7. 14613-37-7 belongs to piperidines, auxiliary class Piperidine,Amine, name is (1-Methylpiperidin-3-yl)methanamine, and the molecular formula is C7H16N2, Safety of (1-Methylpiperidin-3-yl)methanamine.

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

Takahashi, Yusuke published the artcileSynthesis of Biaryls Having a Piperidylmethyl Group Based on Space Integration of Lithiation, Borylation, and Suzuki-Miyaura Coupling, Safety of 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, the publication is European Journal of Organic Chemistry (2020), 2020(5), 618-622, database is CAplus.

In a flow microreactor, aryllithiums bearing a piperidylmethyl group were generated using nBuLi by precise residence time control and effective temperature control, and then selectively borylated with boronic esters such as 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (BpinOiPr) and tri-Me borate B(OMe)₃ by fast mixing. Moreover, the direct integration with Suzuki-Miyaura cross coupling were successfully achieved to obtain nitrogen-containing biaryl compounds The present method could be applied for the straightforward synthesis of the key intermediate of a bioactive component bearing a piperidylmethyl-biphenyl framework.

European Journal of Organic Chemistry published new progress about 859833-21-9. 859833-21-9 belongs to piperidines, auxiliary class Piperidine,Boronic acid and ester,Benzene,Boronic Acids,Boronate Esters, name is 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine, and the molecular formula is C13H16O2, Safety of 1-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)piperidine.

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

Reich, Daniel S. published the artcileSafety and efficacy of tolebrutinib, an oral brain-penetrant BTK inhibitor, in relapsing multiple sclerosis: a phase 2b, randomised, double-blind, placebo-controlled trial, Recommanded Product: (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one, the publication is Lancet Neurology (2021), 20(9), 729-738, database is CAplus and MEDLINE.

Tolebrutinib is an oral, CNS-penetrant, irreversible inhibitor of Bruton’s tyrosine kinase, an enzyme expressed in B lymphocytes and myeloid cells including microglia, which are major drivers of inflammation in multiple sclerosis. We aimed to determine the dose-response relationship between tolebrutinib and the reduction in new active brain MRI lesions in patients with relapsing multiple sclerosis. We did a 16-wk, phase 2b, randomised, double-blind, placebo-controlled, crossover, dose-finding trial at 40 centers (academic sites, specialty clinics, and general neurol. centers) in ten countries in Europe and North America. Eligible participants were adults aged 18-55 years with diagnosed relapsing multiple sclerosis (either relapsing-remitting or relapsing secondary progressive multiple sclerosis), and one or more of the following criteria: at least one relapse within the previous year, at least two relapses within the previous 2 years, or at least one active gadolinium-enhancing brain lesion in the 6 mo before screening. Exclusion criteria included a diagnosis of primary progressive multiple sclerosis or a diagnosis of secondary progressive multiple sclerosis without relapse. We used a two-step randomisation process to randomly assign eligible participants (1:1) to two cohorts, then further randomly assign participants in each cohort (1:1:1:1) to four tolebrutinib dose groups (5, 15, 30, and 60 mg administered once daily as an oral tablet). Cohort 1 received tolebrutinib for 12 wk, then matched placebo (ie, identical looking tablets) for 4 wk; cohort 2 received 4 wk of placebo followed by 12 wk of tolebrutinib. Participants and investigators were masked for dose and tolebrutinib-placebo administration sequence; investigators, study team members, and study participants did not have access to unmasked data. MRI scans were done at screening and every 4 wk over 16 wk. The primary efficacy endpoint was the number of new gadolinium-enhancing lesions detected on the scan done after 12 wk of tolebrutinib treatment (assessed at week 12 for cohort 1 and week 16 for cohort 2), relative to the scan done 4 wk previously, and compared with the lesions accumulated during 4 wk of placebo run-in period in cohort 2. Efficacy data were analyzed in a modified intention-to-treat population, using a two-step multiple comparison procedure with modeling anal. Safety was assessed for all participants who received at least one dose of study drug. This trial is registered with ClinicalTrials.gov (NCT03889639), EudraCT (2018-003927-12), and WHO (U1111-1220-0572), and has been completed. Between May 14, 2019, and Jan 2, 2020, we enrolled and randomly assigned 130 participants to tolebrutinib: 33 to 5 mg, 32 to 15 mg, 33 to 30 mg, and 32 to 60 mg. 129 (99) completed the treatment regimen and 126 were included in the primary anal. At treatment week 12, there was a dose-dependent reduction in the number of new gadolinium-enhancing lesions (mean [SD] lesions per patient: placebo, 1·03 [2·50]; 5 mg, 1·39 [3·20]; 15 mg, 0·77 [1·48]; 30 mg, 0·76 [3·31]; 60 mg, 0·13 [0·43]; p=0·03). One serious adverse event was reported (one patient in the 60 mg group was admitted to hospital because of a multiple sclerosis relapse). The most common non-serious adverse event during tolebrutinib treatment was headache (in one [3] of 33 in the 5 mg group; three [9] of 32 in the 15 mg group; one [3] of 33 in the 30 mg group; and four [13] of 32 in the 60 mg group). No safety-related discontinuations or treatment-related deaths occurred.12 wk of tolebrutinib treatment led to a dose-dependent reduction in new gadolinium-enhancing lesions, the 60 mg dose being the most efficacious, and the drug was well tolerated. Reduction of acute inflammation, combined with the potential to modulate the immune response within the CNS, provides a scientific rationale to pursue phase 3 clin. trials of tolebrutinib in patients with relapsing and progressive forms of multiple sclerosis.Sanofi.

Lancet Neurology published new progress about 1971920-73-6. 1971920-73-6 belongs to piperidines, auxiliary class Other Aliphatic Heterocyclic,Piperidine,Alkenyl,Amine,Benzene,Ether,Inhibitor,Inhibitor, name is (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one, and the molecular formula is C26H25N5O3, Recommanded Product: (R)-1-(1-Acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one.

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

Ekholm, Filip S. published the artcileStudies Related to Norway Spruce Galactoglucomannans: Chemical Synthesis, Conformation Analysis, NMR Spectroscopic Characterization, and Molecular Recognition of Model Compounds, Product Details of C11H15NOS, the publication is Chemistry – A European Journal (2012), 18(45), 14392-14405, database is CAplus and MEDLINE.

Galactoglucomannan (GGM) is a polysaccharide mainly consisting of mannose, glucose, and galactose. GGM is the most abundant hemicellulose in the Norway spruce (Picea abies), but is also found in the cell wall of flax seeds, tobacco plants, and kiwi fruit. Although several applications for GGM polysaccharides have been developed in pulp and paper manufacturing and the food and medical industries, attempts to synthesize and study distinct fragments of this polysaccharide have not been reported previously. Herein, the synthesis of one of the core trisaccharide units of GGM together with a less-abundant tetrasaccharide fragment is described. In addition, detailed NMR spectroscopic characterization of the model compounds, comparison of the spectral data with natural GGM, investigation of the acetyl-group migration phenomena that takes place in the polysaccharide by using small model compounds, and a binding study between the tetrasaccharide model fragment and a galactose-binding protein (the toxin viscumin) are reported.

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, Product Details of C11H15NOS.

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

Boy, Songuel published the artcileSynthesis, Spectroscopic Analysis, and in Vitro/in Silico Biological Studies of Novel Piperidine Derivatives Heterocyclic Schiff-Mannich Base Compounds, HPLC of Formula: 39546-32-2, the publication is Chemistry & Biodiversity (2021), 18(12), e2100433, database is CAplus and MEDLINE.

In the present study, 3-substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (S1-8) were synthesized by treating 4-hydroxybenzaldehyde (B) with eight different 3-substitued-4-amino-4,5-dihydro-1H-1,2,4-triazole-5-ones (T1-8) in acetic acid medium, sep. The synthesized Schiff bases (S) were reacted with formaldehyde and secondary amine such as 4-piperidinecarboxyamide to afford novel heterocyclic bases. 3-Substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (T) were treated with 4-piperidinecarboxyamide in the presence of formaldehyde to synthesize eight new 1-(4-piperidinecarboxyamide-1-yl-methyl)-3-substitued-4-(4-hydroxybenzylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (M1-8). The structure characterization of compounds was carried out using 1H-NMR, IR, HR-MS, and 13C-NMR spectroscopic methods. The inhibitory properties of the newly synthesized compounds were calculated against the acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and glutathione S-transferase (GST) enzymes. Ki values were calculated in the range of 20.06±3.11-36.86±6.17 μM for GST, 17.87±2.91-30.53±4.25 μM for AChE, 9.08±0.69-20.02±2.88 μM for BChE, resp., Besides, IC50 values were also calculated Best binding scores of -inhibitors against used enzymes were calculated as -12.095 kcal/mol, -12.775 kcal/mol, and -9.336 kcal/mol, resp. While 5-oxo-triazole piperidine-4-carboxamide moieties have a critical role in the inhibition of AChE and GST enzymes, hydroxy benzyl moiety is important for BChE enzyme inhibition.

Chemistry & Biodiversity 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, HPLC of Formula: 39546-32-2.

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

Taylor, Doris Mia published the artcileIdentifying Oxacillinase-48 Carbapenemase Inhibitors Using DNA-Encoded Chemical Libraries, Application In Synthesis of 39546-32-2, the publication is ACS Infectious Diseases (2020), 6(5), 1214-1227, database is CAplus and MEDLINE.

Bacterial resistance to β-lactam antibiotics is largely mediated by β-lactamases, which catalyze the hydrolysis of these drugs and continue to emerge in response to antibiotic use. β-Lactamases that hydrolyze the last resort carbapenem class of β-lactam antibiotics (carbapenemases) are a growing global health threat. Inhibitors have been developed to prevent β-lactamase-mediated hydrolysis and restore the efficacy of these antibiotics. However, there are few inhibitors available for problematic carbapenemases such as oxacillinase-48 (OXA-48). A DNA-encoded chem. library approach was used to rapidly screen for compounds that bind and potentially inhibit OXA-48. Using this approach, a hit compound, CDD-97(), was identified with submicromolar potency (K_i = 0.53 ± 0.08μM) against OXA-48. X-ray crystallog. showed that CDD-97 binds noncovalently in the active site of OXA-48. Synthesis and testing of derivatives of CDD-97 revealed structure-activity relationships and informed the design of a compound with a 2-fold increase in potency. CDD-97, however, synergizes poorly with β-lactam antibiotics to inhibit the growth of bacteria expressing OXA-48 due to poor accumulation into E. coli. Despite the low in vivo activity, CDD-97 provides new insights into OXA-48 inhibition and demonstrates the potential of using DNA-encoded chem. technol. to rapidly identify β-lactamase binders and to study β-lactamase inhibition, leading to clin. useful inhibitors.

ACS Infectious Diseases 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 C15H25BN2O4, Application In Synthesis of 39546-32-2.

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

Vettorazzi, Marcela published the artcileAn integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors, Quality Control of 39546-32-2, the publication is European Journal of Medicinal Chemistry (2017), 461-481, database is CAplus and MEDLINE.

Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new mol. target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. The authors’ theor. and exptl. study has allowed the authors to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. The authors’ study was carried out in different steps: virtual screening, synthesis, bioassays and mol. modeling. From the results, the authors propose a new dihydrobenzo[b]pyrimido[5,4-f]azepine and two alkyl{3-/4-[1-hydroxy-2-(4-arylpiperazin-1-yl)ethyl]phenyl}carbamates as initial structures for the development of new inhibitors. In addition, the authors’ mol. modeling study using QTAIM calculations, allowed the authors to describe in detail the mol. interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined to obtain an increase in the binding affinity of these ligands.

European Journal of Medicinal 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 C8H11NO, Quality Control of 39546-32-2.

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

Maricich, Tom J. published the artcileReaction of benzenesulfinyl azide with thiols and amines. Preparation of thiosulfinates and sulfinamides, Recommanded Product: 1-(Phenylsulfinyl)piperidine, the publication is Journal of Organic Chemistry (1984), 49(11), 1931-4, database is CAplus.

Treating PhS(O)N₃ with RSH (R = Ph, PhCH₂, Pr, Me₂CH, Me₃C, HOCH₂CH₂, Me₃CCH₂) at -20° gave PhS(O)SR and HN₃. A similar reaction using R¹NHR² [R¹ = Ph, Bu, HOCH₂CH₂, R² = H; R¹R² = (CH₂)₅] gave PhS(O)NR¹R² and HN₃. Thiosulfinates and sulfinamides containing a free OH group could be prepared Yields ranged from 41 to 93%.

Journal of Organic Chemistry 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, Recommanded Product: 1-(Phenylsulfinyl)piperidine.

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

Fries, David S. published the artcileSynthesis and preliminary pharmacological activity of aminoalkoxy isosteres of glycolate ester anticholinergics, SDS of cas: 13444-24-1, the publication is Journal of Medicinal Chemistry (1977), 20(10), 1250-4, database is CAplus and MEDLINE.

Five 2-[(dialkylamino)alkoxy]-1,1-diphenylethanols and 5 2-(N-heterocycleoxy)-1,1-diphenylethanols were prepared by the reaction of 2,2-diphenyloxirane [882-59-7] with the alkoxide form of the appropriate amino alc. Most of the compounds had moderate anticholinergic activity when tested on the isolated rat jejunum or for inhibition of perphenazine-induced catatonia in rats. The most active compounds were I [63624-24-8], II [63624-25-9], and III [63624-26-0]. Structure-activity relations are discussed.

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 C7H15NO, SDS of cas: 13444-24-1.

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