Tag: M.W=100-150

Nadaf, AfraQuasar A. published the artcileSynthesis of N-(4-(6-chloro-imidazo[1,2-a]pyridin-2-yl)phenyl) Acetamide Derivatives as Antitubercular Agents, Quality Control of 39546-32-2, the publication is ChemistrySelect (2020), 5(45), 14422-14429, database is CAplus.

The present article reported the synthesis of N-(4-(6-chloroH-imidazo[1,2-a]pyridin-2-yl)phenyl)acetamide derivatives (PINRAc) I [R = piperidin-1-yl, morpholin-4-yl, cyclohexylaminyl, etc.] using 5-chloropyridin-2-amine and 2-bromo-1-(4-nitrophenyl)ethanone in a multi-step protocol. The structures of all the compounds I were characterized by NMR, FT-IR and GCMS. The compounds I were screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv using the microplate Alamar Blue assay. Most of them exhibited good antitubercular activity with MIC in the range of 1.6-25μg/mL and the cytotoxicity study carried out on human embryonic kidney cell line showed no toxicity on the normal cells. The docking study was performed on mycolic acid transporter protein MmpL3 from Mycobacterium smegmatis which supported the in-vitro results.

ChemistrySelect 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, Quality Control of 39546-32-2.

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

Grandberg, I. I. published the artcileDemjanov rearrangement in a series of nitrogenous heterocycles, Application In Synthesis of 14613-37-7, the publication is Doklady TSKhA (1970), 226-31, database is CAplus.

Three isomeric compounds, 2-, 3- and 4-aminomethyl-N-methylpiperidine, were diazotized and the degradation products obtained at 0°, pH 5.5, separated and identified. The 2-substituted derivative gave 2-hydroxymethyl-N-methylpiperidine, 6-methylaminohexan-2-one, 1,2-dimethylpiperidin-2-one, and 2,3-dehydro-1-methylhexamethylenimine in the proportion 49:16:-26:9. The 3-substituted derivative gave 3-hydroxymethyl-N-methylpiperidine, 3(4)-hydroxy-1-methylhexamethylenimine, 1,-3-dimethyl-3-hydroxypiperidine, 2 unsaturated piperidine derivatives (estimated together) and an unsaturated hexamethylenimine derivatives in the proportion 62:2:14:16:6. The ratios of corresponding products with the 4-substituted derivative were 38:1:39:16:6. Two mechanisms based on the conformation of the piperidine ring are proposed to explain the unusually low ratio of rearrangement products and the predominance of H over C atom migration in these reactions.

Doklady TSKhA 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, Application In Synthesis of 14613-37-7.

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

Vil’yams, V. V. published the artcileThe ring isomerization in some nitrogen-containing heterocyclic compounds. Synthesis of amino and hydroxy derivatives of β-methylpiperidine, Formula: C7H16N2, the publication is Dokl., Rossiisk. Sel’skokhoz. Akad. (1964), 553-7, database is CAplus.

The synthesis of 1-methyl-3-(aminomethyl)piperidine (I) and 3-piperidinylmethanol (II) was described. A mixture of 61 g. nicotinamide, 106.5 g. MeI, 200 ml. MeOH, and a trace of nicotinamide methiodide was refluxed 3 hrs., the solution evaporated in vacuo, the residue dissolved in 150 ml. H₂O and boiled with freshly prepared AgCl (from 120 g. AgNO₃ and 42 g. NaCl) for 5 hrs. The reaction mixture was filtered (charcoal) and hydrogenated over 0.4 g. PtO₂ 36 hrs. at 3.5-1.5 atm. to give 87% nipecotamide methochloride (III), m. 239°. III heated with an equal amount P₂O₅ 5 hrs. at 180°, treated with hot H₂O, neutralized with K₂CO₃, and extracted with AcOEt yielded 76% 1-methyl-3-cyanopiperidine (IV), b₂₃ 106°, b₁₄ 92°, n²⁰_D 1.4630, d²⁰₂₀ 0.9560, surface tension σ₂₀ 34.34 ergs/cm.² To a solution of 6.5 g. LiAlH₄ in 600 ml. absolute Et₂O at 0°, a solution of 25 g. IV in 200 ml. absolute Et₂O was added dropwise during 2 hrs., and the mixture left overnight at room temperature and then refluxed 1.5 hrs. After the usual treatment, 89% I was obtained, b₄ 52°, n²⁰_D 1.4739, d²⁰₂₀ 0.9096, σ₂₀ 32.67 ergs/cm.² [I.PtCl₆ m. 212° (decomposition); I.(AuCl₄)₂ m. 177° (decomposition); picrate m. 234° (decomposition)]. A solution of 30.2 g. Et nicotinate (b₃ 77-80°, n¹⁶_D 1.504, d¹⁶₁₆ 1.1136, σ₂₀ 37.23 ergs/cm.²) in 600 ml. absolute EtOH was added to 62 g. Na, the reaction completed by short refluxing, and the solution decomposed by addition of 150 ml. H₂O, concentrated in vacuo, and extracted with AcOEt. After fractionation, 57% II was obtained, b₃ 103-4°, n²⁰_D 1.4971, d²⁰₂₀ 1.0283, σ₂₀ 44.39 ergs/cm.²

Dokl., Rossiisk. Sel’skokhoz. Akad. 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 C3H6O2, Formula: C7H16N2.

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

Vil’yams, V. V. published the artcileRing isomerization of nitrogen heterocycles. Reaction of N-methyl-3-aminomethylpiperidine with nitrous acid, Application In Synthesis of 14613-37-7, the publication is Doklady TSKhA (1965), No. 115(Pt. 1), 247-53, database is CAplus.

N-Methyl-3-aminomethylpiperidine (I) diazotized under the conditions of Demjanov rearrangement gave 39.8% N-methyl-3-hydroxymethylpiperidine (II), about 5% N-methyl-3-methyltetrahydropyridine (III), and 15% 1-methyl-1,5,5,6-tetrahydro-2H-azepine (IV). To the ice-cooled solution of 25.6 g. I and 28.8 g. 85% H₃PO₄ in 200 cc. H₂O was added 14.5 g. NaNO₂ in 50 cc. H₂O, the mixture heated, saturated with Na₂CO₃, and extracted with dichloroethane to give 1.14 g. 1:4.4 mixture of III and IV (b₅₅ 84-90°, d²⁰₂₀0 0.8514, n²⁰_D 1.4585, MR_D 35.61), 10.27 g. of II, b_1.5 63-4°, d²⁰₂₀ 0.9745, n²⁰_D 1.4771, δ₂₀ 34.69 erg/cm.², MR_D 37.47; chloroplatinate m. 213° (decomposition) (EtOH-Et₂O). II was also obtained in 74.9% yield by reduction of ethyl N-methyl nicotinate (V) with LiAlH₄ in Et₂O. V, b₁ 46-7°, d²⁰₂₀ 0.9773, n²⁰_D 1.4545, MR_D 47.175, was prepared in 89.3% yield as follows: 15.1 g. Et nicotinate was refluxed 6 hrs. with 21.3 g. MeI in 50 cc. MeOH, the solvent evaporated, the residue dissolved in 50 cc. H₂O, and the solution treated with freshly prepared AgCl (from 25.5 g. AgNO₃ and 9.36 g. NaCl) and after filtration hydrogenated over Pt at 3 atm. 23 references.

Doklady TSKhA 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 C14H12O2, Application In Synthesis of 14613-37-7.

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

Bryan, Marian C. published the artcileDevelopment of Potent and Selective Pyrazolopyrimidine IRAK4 Inhibitors, Application of Piperidine-4-carboxamide, the publication is Journal of Medicinal Chemistry (2019), 62(13), 6223-6240, database is CAplus and MEDLINE.

A series of pyrazolopyrimidine inhibitors of IRAK4 were developed from a high-throughput screen (HTS). Modification of an HTS hit led to a series of bicyclic heterocycles with improved potency and kinase selectivity but lacking sufficient solubility to progress in vivo. Structure-based drug design, informed by cocrystal structures with the protein and small-mol. crystal structures, yielded a series of dihydrobenzofurans. This semisatd. bicycle provided superior druglike properties while maintaining excellent potency and selectivity. Improved physicochem. properties allowed for progression into in vivo experiments, where lead mols. exhibited low clearance and showed target-based inhibition of IRAK4 signaling in an inflammation-mediated PK/PD mouse model.

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 C6H12N2O, Application of Piperidine-4-carboxamide.

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

Gholivand, Khodayar published the artcileSynthesis, biological evaluation, QSAR study and molecular docking of novel N-(4-amino carbonylpiperazinyl) (thio)phosphoramide derivatives as cholinesterase inhibitors, Synthetic Route of 39546-32-2, the publication is Pesticide Biochemistry and Physiology (2014), 40-50, database is CAplus and MEDLINE.

Novel (thio)phosphoramidate derivatives based on piperidincarboxamide with the general formula of (NH₂-C(O)-C₅H₉N)-P(X = O,S)R₁R₂ (1-5) and (NH₂-C(O)-C₅H₉N)₂-P(O)R (6-9) were synthesized and characterized by ³¹P, ¹³C, ¹H NMR, IR spectroscopy. Furthermore, the crystal structure of compound (NH₂-C(O)-C₅H₉N)₂-P(O)(OC₆H₅) (6) was investigated. The activities of derivatives on cholinesterases (ChE) were determined using a modified Ellman’s method. Also the mixed-type mechanisms of these compounds were evaluated by Lineweaver-Burk plots. Mol. docking and quant. structure-activity relationship (QSAR) were used to understand the relationship between mol. structural features and anti-ChE activity, and to predict the binding affinity of phosphoramido-piperidinecarboxamides (PAPCAs) to ChE receptors. From mol. docking anal., noncovalent interactions especially hydrogen bonding as well as hydrophobic was found between PAPCAs and ChE. Based on the docking results, appropriate mol. structural parameters were adopted to develop a QSAR model. DFT-QSAR models for ChE enzymes demonstrated the importance of electrophilicity parameter in describing the anti-AChE and anti-BChE activities of the synthesized compounds The correlation matrix of QSAR models and docking anal. confirmed that electrophilicity descriptor can control the influence of the hydrophobic properties of P = (O, S) and C=O functional groups of PAPCA derivatives in the inhibition of human ChE enzymes.

Pesticide Biochemistry and Physiology 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, Synthetic Route of 39546-32-2.

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

Potowski, Marco published the artcileTranslation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis, Recommanded Product: Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry (2020), 28(9), 115441, database is CAplus and MEDLINE.

The Petasis three-component reaction gives rise to diverse substituted α-aryl glycines from readily available amines, boronic acids and glyoxalic acid. Thus, this reaction is highly attractive for DNA-encoded small mol. screening library synthesis. The Petasis reaction is for instance promoted by a potentially DNA damaging copper(I)/bipyridine reagent system in dry organic solvents. We found that solid phase-coupled DNA strands tolerated this reagent system at elevated temperature allowing for synthesis of diverse substituted DNA-tagged α-aryl glycines from DNA-conjugated secondary amines.

Bioorganic & 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 C6H12N2O, Recommanded Product: Piperidine-4-carboxamide.

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

Zuo, Zeping published the artcileDesign and biological evaluation of tetrahydropyridine derivatives as novel human GPR119 agonists, Recommanded Product: Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry Letters (2020), 30(4), 126855, database is CAplus and MEDLINE.

A series of novel tetrahydropyridine derivatives were prepared and evaluated using cell-based measurements. Systematic optimization of general structure G-1 led to the identification of compound 4-((4-(1H-tetrazol-1-yl)phenoxy)methyl)-2-(1-(5-ethylpyrimidin-2-yl)1,2,3,6-tetrahydropyridin-4-yl)thiazole (EC₅₀ = 4.9 nM) and 2-(1-(5-ethylpyrimidin-2-yl)-1,2,3,6-tetrahydropyridin-4-yl)-4-((2-fluoro-4(1H-tetrazol-1-yl)phenoxy)methyl)thiazole (EC₅₀ = 8.8 nM) with high GPR119 agonism activity and moderate clog P. Through single and long-term pharmacodynamic experiments, compound 4-((4-(1H-tetrazol-1-yl)phenoxy)methyl)-2-(1-(5-ethylpyrimidin-2-yl)1,2,3,6-tetrahydropyridin-4-yl)thiazole showed a hypoglycemic effect and may have an effect on improving basal metabolic rate in DIO mice. Both in vitro and in vivo tests indicated that compound 4-((4-(1H-tetrazol-1-yl)phenoxy)methyl)-2-(1-(5-ethylpyrimidin-2-yl)1,2,3,6-tetrahydropyridin-4-yl)thiazole was a potential potent GPR119 agonist in allusion to T2DM treatment.

Bioorganic & Medicinal Chemistry Letters 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 C9H7NO2, Recommanded Product: Piperidine-4-carboxamide.

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

Sundriyal, Sandeep published the artcileHistone lysine methyltransferase structure activity relationships that allow for segregation of G9a inhibition and anti-Plasmodium activity, Application In Synthesis of 39546-32-2, the publication is MedChemComm (2017), 8(5), 1069-1092, database is CAplus and MEDLINE.

Plasmodium falciparum HKMTs (PfHKMTs) play a key role in controlling Plasmodium gene expression and represent exciting new anti-malarial epigenetic targets. Using an inhibitor series derived from the diaminoquinazoline HKMT inhibitory chemotype, we have previously identified compounds with highly promising antimalarial activity, including irreversible asexual cycle blood stage-independent cytotoxic activity at nM concentrations, oral efficacy in in vivo models of disease, and the unprecedented ability to reactivate dormant liver stage parasites (hypnozoites). However, future development of this series will need to address host vs. parasite selectivity, where inhibitory activity against human G9a is removed from the lead compounds, while maintaining potent anti-Plasmodium activity. Herein, we report an extensive study of the SAR of this series against both G9a and P. falciparum. We have identified key SAR features which demonstrate that high parasite vs. G9a selectivity can be achieved by selecting appropriate substituents at position 2, 4 and 7 of the quinazoline ring. We have also, in turn, discovered that potent G9a inhibitors can be identified by employing a 6-carbon ‘Nle mimic’ at position 7. Together, this data suggests that while broadly similar, the G9a and potential PfHKMT target(s) binding pockets and/or binding modes of the diaminoquinazoline analogs exhibit clear and exploitable differences. Based on this, we believe this scaffold to have clear potential for development into a novel anti-malarial therapeutic.

MedChemComm 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 C6H8N2, Application In Synthesis of 39546-32-2.

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

Mo, Jun published the artcileDesign, synthesis, in vitro and in vivo evaluation of benzylpiperidine-linked 1,3-dimethylbenzimidazolinones as cholinesterase inhibitors against Alzheimer’s disease, HPLC of Formula: 39546-32-2, the publication is Journal of Enzyme Inhibition and Medicinal Chemistry (2020), 35(1), 330-343, database is CAplus and MEDLINE.

Cholinesterase inhibitor plays an important role in the treatment of patients with Alzheimer’s disease (AD). Herein, we report the medicinal chem. efforts leading to a new series of 1,3-dimethylbenzimidazolinone derivatives Among the synthesized compounds, and showed submicromolar IC₅₀ values (, eeAChE IC₅₀ = 0.39 ± 0.11μM; , eqBChE IC₅₀ = 0.16 ± 0.04μM) towards acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Kinetic and mol. modeling studies revealed that and act in a competitive manner. and showed neuroprotective effect against H₂O₂-induced oxidative damage on PC12 cells. This effect was further supported by their antioxidant activity determined in a DPPH assay in vitro. Morris water maze test confirmed the memory amelioration effect of the two compounds in a scopolamine-induced mouse model. Moreover, the hepatotoxicity of and was lower than tacrine. In summary, these data suggest and are promising multifunctional agents against AD.

Journal of Enzyme Inhibition and 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 C6H12N2O, HPLC of Formula: 39546-32-2.

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