Tag: M.W=100-150

Akiyama, Yoshikatsu published the artcileSynthesis of Temperature-Responsive Polymers Containing Piperidine Carboxamide and N,N-diethylcarbamoly Piperidine Moiety via RAFT Polymerization, Product Details of C6H12N2O, the publication is Macromolecular Rapid Communications (2021), 42(15), 2100208, database is CAplus and MEDLINE.

In this study, poly(N-acryloylnipecotamide) (PNANAm), poly(N-acryloylisonipecotamide) (PNAiNAm), and poly(N-acryloyl-N,N-diethylnipecotamide) (PNADNAm) are synthesized as temperature-responsive polymers using reversible addition-fragmentation chain-transfer polymerization Aqueous solutions of the three polymers are examined via temperature-dependent optical transmittance measurements. The PNANAm sample with a hydrophilic terminal group shows an upper critical solution temperature (UCST) in phosphate-buffered saline (PBS) when its mol. weight (M_n) is �7600, whereas PNANAm (M_n < 7600) is soluble The UCST is influenced by mol. weight and polymer concentration In contrast, PNANAm sample with nonionic terminal group shows UCST, when M_n is < 7600, suggesting that the terminal nonionic group possibly increases UCST of PNANAm. The urea addition experiment suggests that the driving force for expression of UCST of PNANAm is the formation of inter- and intramol. hydrogen bonds among the polymer chains. PNAiNAm is soluble in PBS but exhibits an UCST in an appropriate concentration of ammonium sulfate. In contrast, PNADNAm exhibits a lower critical solution temperature Comparing the chem. structure of these polymers and their phase transition behaviors suggests that the carboxamide group position in the piperidine ring could determine the UCST expression. The results could help design temperature-responsive polymers with a desired cloud point temperature

Macromolecular Rapid Communications 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, Product Details of C6H12N2O.

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

Deguchi, Yoshio published the artcilePiperidine derivatives, Computed Properties of 14613-37-7, the publication is Iyaku Shigen Kenkyusho Nempo (1956), 17-22, database is CAplus.

Dialkylureido-N-methylpiperidines and dialkylureidomethyl-N-methylpiperidines were prepared Pyridine-3-carboxylic acid amide (10 g.) is refluxed with 17.5 g. MeI and 30 cc. MeOH for 5 hrs., evaporated, the residue is dissolved in 30 cc. H₂O, warmed with freshly prepared AgCl (prepared from 20 g. AgNO₃ and 7 g. NaCl) for 3 hrs., and filtered. The filtrate is decolorized with active C and then catalytically reduced with 0.1 g. PtO₂ to give 85% N-methylpiperidine-3-carboxamide (I); hydrochloride m. 232° (alc.). Similarly was prepared N-methylpiperidine-4-carboxamide; hydrochloride, hygroscopic. A mixture of 7 g. I and 7 g. P₂O₅ is heated at 160-180° for 3 hrs., cooled, dissolved in 50 cc. H₂O with warming, neutralized with K₂CO₃, salted out, and the separated oil extracted with AcOEt to give 80% 3-cyano-N-methylpiperidine (II), b₂₀ 95-6°. Similarly was prepared 4-cyano-N-methylpiperidine, b₂₁ 97°. Into a cooled mixture of 1.3 g. LiAlH₄ and 150 cc. Et₂O is dropped a solution of 5.0 g. II in 50 cc. Et₂O during 90 min., the mixture stirred 1 hr., refluxed 30 min., 15 cc. H₂O added to decompose excess LiAlH₄, and filtered. The filtrate is dried with KOH, evaporated, and distilled in vacuo to give 90% 3-aminomethyl-N-methylpiperidine (III), b₂₀ 81-2°; dipicrate m. 231° (decomposition). Similarly was prepared 4-aminomethyl-N-methylpiperidine (IV), b₂₀ 80-1°; dipicrate m. 236° (decomposition). To a mixture of 32 g. KOH, 6.4 g. Br, and 400 cc. H₂O is dropped an aqueous solution of 5.7 g. I under ice cooling, then warmed at 70° for 1 hr., alkalized with KOH, distilled with steam, and the distilled solution treated with diluted HCl, concentrated in vacuo, alkalized with KOH, extracted with Et₂O, and the extract evaporated and distilled in vacuo to give 65% 3-amino-N-methylpiperidine (V), b₄₃ 74-5°; dipicrate m. 227° (decomposition). Similarly was prepared 4-amino-N-methyl-piperidine (VI), b₃₅ 70-1°; dipicrate m. 263° (decomposition). A mixture of 0.6 mole Me₂NH and 200 cc. PhMe is dropped into 50% phosgene-PhMe, refluxed 1 hr., and distilled in vacuo to give 40% dimethylcarbamoyl chloride (VII), b_55-60 85-8°. Similarly was prepared diethylcarbamoyl chloride (VIII), b_17-20 80°. A mixture of 2 moles III and 1 mole VII in Et₂O is kept at room temperature 1.5 hrs., refluxed 10 min., cooled, and filtered. The filtrate is evaporated and chromatographed using alumina to give 3-dimethylureidomethyl-N-methyl-piperidine, needles (petr.-ether), m. 66-9° (hygroscopic). Similarly were prepared following IX (starting materials, position of substituent, n, R, appearance, and m.p. given): III and VIII, 3, 1, Et, sirupy, -; IV and VII, 4, 1, Me, needles (hygroscopic), 40-4° (hydrochloride m. 230°); IV and VIII, 4, 1, Et, columns, 66-8°; V and VIII, 3, 0, Me, needles, 110-12°; V and VIII, 3, 1, Et, sirupy, (picrolonate m. 195-7°); VI and VII, 4, 0, Me, flakes, 138-9°; VI and VIII, 4, 0, Et, needles, 89-90°.

Iyaku Shigen Kenkyusho Nempo 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, Computed Properties of 14613-37-7.

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

Manap, Sevda published the artcileSynthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives, COA of Formula: C6H12N2O, the publication is Journal of the Iranian Chemical Society (2022), 19(4), 1347-1368, database is CAplus.

The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones I (R = Me, Ph, Bn, etc.) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones II (R¹ = H). Moreover, their five N-acetyl derivatives II (R¹ = acetyl) were synthesized. Besides, compounds II (R¹ = morpholin-4-yl-methyl)/II (R¹ = N-methylpiperazinyl)/II (R¹ = (4-carbamoylpiperidin-1-yl)methyl)/III were obtained by Mannich reaction between compounds II (R¹ = H) and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.

Journal of the Iranian Chemical Society 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, COA of Formula: C6H12N2O.

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

Mitchell, Robin E. published the artcileSynthesis of amino acid conjugates to 2-imino-3-methylene-5-carboxypyrrolidine and 2-imino-3-methylene-6-carboxypiperidine, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(6), 1910-1912, database is CAplus and MEDLINE.

The four stereomers of 2-imino-3-methylene-5-(carboxy-L-valyl)pyrrolidine, a bacterial metabolite that is inhibitory to the fire blight bacterium Erwinia amylovora, were synthesized and compared for antibacterial activity. Several alternative amino acid conjugates with L,L-stereochem. were also prepared, and the synthesis was extended to 3-methylenepiperidine-6-L-carboxylic acid and a selection of 2-imino-3-methylenepiperidine-6-L-carboxy-L-amino acid conjugates. All synthetic amino acid conjugates (L,L-stereomers) were inhibitory to the growth of E. amylovora. The likely participation of the conjugated iminomethylene moiety as a Michael acceptor is implicated.

Bioorganic & Medicinal Chemistry Letters published new progress about 72002-30-3. 72002-30-3 belongs to piperidines, auxiliary class Piperidine,Chiral,Carboxylic acid,Amide, name is (R)-6-Oxopiperidine-2-carboxylic acid, and the molecular formula is C6H9NO3, Recommanded Product: (R)-6-Oxopiperidine-2-carboxylic acid.

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

Paul, Raymond published the artcileDerivatives of 3-hydroxypiperidine, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Compt. rend. (1945), 221(No. 15), 412-14, database is CAplus.

1,2-Epoxy-5-chloropentane (I) reacts with amines in most cases to form piperidine derivatives I and 1 mol. NHEt₂ at 100° form a colorless solid, apparently the 1-ethyl-3-hydroxypiperidine-EtCl (II). II warmed with concentrated KOH gives C₂H₄ and 1-ethyl-3-hydroxypiperidine (III), b₂₁ 97-98°, d₁₅²³ 0.966, n_D²³ 1.47427 (77% yield based on I). The intermediate 1-diethylamino-5-chloropentane is not isolated. N,N-Diethyltetrahydrofurfurylamine reacts with dry HBr to form a water-soluble product, which reacts with NH₃ to form the ethobromide (IV) of III. IV warmed with concentrated KOH gave C₂H₄ and 74% of III. I and EtNH₂ at 100° form a product which reacts in hot KOH solution to give 74% of III. BzCl and III form the HCl salt of the benzoate ester, colorless needles, m. 204° and possessing marked anesthetic properties. III and excess concentrated HCl at 150° or III and 1 mol. SOCl₂ at 100-120° give 1-ethyl-3-chloropiperidine (V), colorless liquid of moldy odor, b₂₀ 75°, d₁₅^19.5 0.996, n_D^19.5 1.46807. Picrate of V m. 156-7°; methiodide, m. about 210 °. Aniline and 1 mol. I give at 120° 1-phenyl-3-hydroxypiperidine, colorless liquid, b₁₆ 176°, d₁₆¹⁵ 1.099, n_D¹⁵ 1.57856, and not N-phenyltetrahydrofurfurylamine (VI), b₁₀ 155-6°, d₁₆¹¹ 1.075, n_D¹¹ 1.56456, which was obtained by the action of aniline and tetrahydrofurfuryl chloride (VII) at 150°. The piperidine ring is not always formed, as shown by the action of PhNHEt on I for 12 h. at 125°. N-Tetrahydrofurfuryl-N-ethylaniline (VIII), b₂₀ 176-7°, d₁₆²² 1.052, n_D²² 1.55962, was formed. VIII was also obtained by direct action of PhNHEt on VII.

Compt. rend. 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, Recommanded Product: 1-Ethylpiperidin-3-ol.

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

Reitsema, Robert H. published the artcileNovel rearrangement of a piperidine ring, Application In Synthesis of 13444-24-1, the publication is Journal of the American Chemical Society (1949), 2041-3, database is CAplus.

cf. C.A. 43, 6206i. 1-Ethyl-3-chloropiperidine-HCl (I) (18.4 g.) and 21.4 g. PhCH₂NH₂ in 20 cc. H₂O, heated 48 hrs. at 65-75°, give 73.4% 1-ethyl-2-(benzylaminomethyl)pyrrolidine (II), b₁ 134° (dipicrate, m. 190-1°). 1-Methyl-3-chloropiperidine yields 42% of the 1-Me homolog of II, b_0.2-0.3 110-12° (dipicrate, m. 172-3°). II (2.18 g.) in 50 cc. absolute EtOH, shaken overnight with 2 g. Pd-C (but not with Pt oxide) at 50°, gives 1-ethyl-2-(aminomethyl)pyrrolidine (III), whose dipicrate m. 177-8.5°; III results also from I and alc. NH₃ (20 days at room temperature). I (16 g.), 30.2 g. 8-amino-6-methoxyquinoline, and 25 cc. H₂O, heated 20 hrs. at 60-70° and 2 hrs. at 110°, give 9.1 g. 6-methoxy-8-(1-ethyl-2-pyrrolidylmethylamino)quinoline (IV), b_0.2 186-90°, whose di-HCl salt m. 214-16°, and dipicrate m. 202.5-3.5°. 1-Ethyl-3-piperidone, reduced in MeOH over Raney Ni at 125° and 2270 lb., gives 1-ethyl-3-hydroxypiperidine, whose benzoate-HCl m. 197-8°. IV is less effective for clinical use than many of the new antimalarials.

Journal of the American Chemical Society 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 In Synthesis of 13444-24-1.

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

Zheng, Peiyuan published the artcileDesign, synthesis and biological evaluation of imidazo[1,5-a]pyrazin-8(7H)-one derivatives as BRD9 inhibitors, Category: piperidines, the publication is Bioorganic & Medicinal Chemistry (2019), 27(7), 1391-1404, database is CAplus and MEDLINE.

BRD9 is the subunit of mammalian SWI/SNF chromatin remodeling complex (BAF). SWI/SNF complex mutations were found in nearly 20% of human cancers. The biol. role played by BRD9 bromodomain remains poorly understood, and it is therefore imperative to identify potent and highly selective inhibitors to effectively explore the biol. of individual bromodomain proteins. In this paper, we synthesized a series of imidazo[1,5-a]pyrazin-8(7H)-one derivatives as potent BRD9 inhibitors and evaluated their BRD9 inhibitory activity in vitro and anti-proliferation effects against tumor cells. Gratifyingly, compound 27(I) and 29(II) exhibited robust potency of BRD9 inhibition with IC₅₀ values of 35 and 103 nM resp. Docking studies were performed to explain the structure-activity relationship. Furthermore, I potently inhibited cell proliferation in cell lines A549 and EOL-1 with an IC₅₀ value of 6.12 μM and 1.76 μM resp. The chem. probe, I, was identified that should prove to be useful in further exploring BRD9 bromodomain biol. in both in vitro and in vivo settings.

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 C7H16Cl2Si, Category: piperidines.

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

Cheng, Yarui published the artcileNew insights into the function of the proteins IsiC and IsiD from Synechocystis sp. PCC 6803 under iron limitation, Quality Control of 39546-32-2, the publication is Applied Microbiology and Biotechnology (2021), 105(11), 4693-4707, database is CAplus and MEDLINE.

Iron is a common cofactor in biol. processes such as respiration, photosynthesis, and nitrogen fixation. The genes isiC and isiD encode unknown proteins, and the growth of ΔisiC and ΔisiD mutants is inhibited under iron-deficient conditions. To study the regulatory mechanisms of IsiC and IsiD during iron starvation, we carried out transcriptome and metabolome sequencing. The Kyoto Encyclopedia of Genes and Genomes (KEGG) anal. showed that the photosynthesis, nitrogen metabolism, and ABC transporter pathways play a vital role in regulating iron deficiency. Upon iron repletion, IsiC and IsiD also have a regulatory effect on these pathways. Addnl., KEGG anal. of the differential metabolites of wild type (WT) and mutants showed that they were all enriched in starch and sucrose metabolism after iron limitation. Weighted gene co-expression network anal. (WGCNA) constructed a co-expression network of differentially expressed genes with phenotypes and metabolites, and finally identified five modules. The turquoise module was pos. correlated with iron deficiency. In contrast, the WT and blue module exhibited a neg. correlation, and the mutants ΔisiC and ΔisiD were pos. correlated with the gray and brown modules, resp. WGCNA also analyzed the relationship between metabolites and phenotypes, and the green module was related to iron starvation. The co-expression network determined the hub genes and metabolites of each module. This study lays a foundation for a better understanding of cyanobacteria in response to iron deficiency.

Applied Microbiology and Biotechnology 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

Cai, Dong published the artcileExploring new structural features of the 18β-glycyrrhetinic acid scaffold for the inhibition of anaplastic lymphoma kinase, Application of Piperidine-4-carboxamide, the publication is Molecules (2019), 24(19), 3631pp., database is CAplus and MEDLINE.

Novel 18β-glycyrrhetinic acid derivatives possessing a carbamate moiety I [R = 4-ClC₆H₄, 3,4-di-ClC₆H₃, 4-Cl-3-CF₃C₆H₃, etc.; R¹ = OH, morpholino] and structurally similar ester derivatives II [R² = 4-ClC₆H₄CH₂, (4-methylpiperazin-1-yl)methyl, (4-formyl-1-piperidyl)methyl, etc.] were developed and evaluated for their efficacy as antitumor inhibitors. In the cellular assays, most of the N-substituted carbamate derivatives I at the C3-position exhibited potent activities. The results of SAR investigation revealed that the introduction of the morpholine group at the C30-COOH led to a significant loss of the inhibitory potency. Among the ester derivatives, the ester group at C3-position also determined a noticeable reduction in the efficacy. Compound I [R = 3-CF₃C₆H₄; R¹ = OH] exhibited the most prominent antiproliferative activity against six human cancer cells (A549, HT29, HepG2, MCF-7, PC-3, and Karpas299). Furthermore, compound I [R = 3-CF₃C₆H₄; R¹ = OH] exerted a moderate inhibiting effect on the ALK. The results of mol. docking analyses suggested that it could bind well to the active site of the receptor ALK, which was consistent with the biol. data. These results might inspire further structural optimization of 18β-glycyrrhetinic acid aiming at the development of potent antitumor agents. The structures I [R = 4-ClC₆H₄, 4-BrC₆H₄, 4-FC₆H₄, 3-CF₃C₆H₄, 4-CF₃OC₆H₄; R¹ = morpholino] were studied by X-ray crystallog. analyses.

Molecules 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

Wu, Qifan published the artcileDiscovery of Novel Piperidinylthiazole Derivatives As Broad-Spectrum Fungicidal Candidates, Category: piperidines, the publication is Journal of Agricultural and Food Chemistry (2019), 67(5), 1360-1370, database is CAplus and MEDLINE.

Oxathiapiprolin is one of the best active fungicides discovered for oomycetes control. To develop a fungicide candidate with a broad spectrum of activity, 22 new piperidinylthiazole derivatives were designed and synthesized. Compound (I) showed the best activity against Pseudoperonospora cubensis (Berk. et Curt.) Rostov and Phytophthora infestans in vivo with 100% and 80% of inhibition, resp., at 1 mg/L, and 72.87% of field efficacy against P. cubensis at 1 g ai/667 m² validated these results. Compound (II) exhibited a broad spectrum of excellent activity against Sclerotinia sclerotiorum with EC₅₀ = 0.30 mg/L (>10 times more active than oxathiapiprolin and azoxystrobin in vitro), good activity against Botrytis cinerea, Cercospora arachidicola, and Gibberella zeae with EC₅₀ of 14.54, 5.57, and 14.03 mg/L in vitro and against P. cubensis and P. infestans with 60% and 30% inhibition rates, resp., at 1 mg/L in vivo. Mode of action studies by RNA sequencing anal. discovered oxysterol-binding protein (OSBP), chitin synthase (CHS1), and (1,3)-β-glucan synthase (FKS2) as the potent target of II against S. sclerotiorum. Quenching studies validated that OSBP was the same target of both II and oxathiapiprolin; it was quenched by both of them. Our studies discovered isothiazole-containing piperidinylthiazole as an OSBP target-based novel lead for fungicide development.

Journal of Agricultural and Food 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 C11H8O3, Category: piperidines.

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