Tag: M.W=100-150

Karaluka, Valerija published the artcileB(OCH₂CF₃)₃-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether, Quality Control of 39546-32-2, the publication is Organic & Biomolecular Chemistry (2015), 13(44), 10888-10894, database is CAplus and MEDLINE.

The use of B(OCH₂CF₃)₃ for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl Me ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined Further optimization of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

Organic & Biomolecular 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, Quality Control of 39546-32-2.

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

Van Luppen, J. J. published the artcileNMR study on trapping techniques to deduce the conformations of 1-alkyl-3-hydroxypiperidines, Product Details of C7H15NO, the publication is Organic Magnetic Resonance (1982), 18(4), 199-206, database is CAplus.

The conformational equilibrium of the title compounds [I; R = H, Me, Et, Pr, Bu, CHMe₂, CHMeEt, (CH₂)₄Me, CHMePr] was examined in hexane and H₂O. The most reliable results were obtained by conformational trapping in D₂SO₄/D₂O and anal. by ¹H and ¹³C NMR. In an apolar solvent, the conformation with an axial group always predominates (69%). In aqueous acid solution of pH 5 the same conformation predominates (56%); in aqueous base of pH âˆ?1 the axial-OH conformer accounted for only 43% of the mols. The results were compared with those obtained by other methods, e.g. IR.

Organic Magnetic Resonance 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 C19H17N2NaO4S, Product Details of C7H15NO.

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

Kuehl, Nikos published the artcileBeyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture, Quality Control of 39546-32-2, the publication is Journal of Medicinal Chemistry (2021), 64(8), 4567-4587, database is CAplus and MEDLINE.

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The mol. recognition preferences of the protease favor basic, pos. charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-mol. inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC₅₀ 0.24μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclin. development.

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, Quality Control of 39546-32-2.

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

Ji, Qinggang published the artcileDesign, synthesis and biological evaluation of novel diazaspirodecanone derivatives containing piperidine-4-carboxamide as chitin synthase inhibitors and antifungal agents, Name: Piperidine-4-carboxamide, the publication is Bioorganic Chemistry (2021), 105108, database is CAplus and MEDLINE.

A series of novel 2-oxo-(1-oxo-2,8-diazaspiro[4.5]decane-8-yl)ethylpiperidine carboxamide derivatives were designed, synthesized and characterized by 1H NMR, 13C NMR and HRMS spectroscopy. All eighteen newly prepared compounds were evaluated for their inhibition against chitin synthase (CHS) and antifungal activities in vitro. The enzyme assay revealed that compound 5h showed excellent inhibitory activity against CHS with IC50 value of 0.10 mM, and the compounds 5b, 5d and 5q showed good inhibition against chitin synthase with IC50 values of 0.13 mM, 0.18 mM and 0.15 mM, resp., while IC50 value of ployoxin B was 0.08 mM. Meanwhile, the others of these compounds exhibited moderate inhibition potency against chitin synthase. The antifungal assay showed compound 5h had excellent antifungal activity compared with the control drugs fluconazole and polyoxin B against these tested strains including C. albicans, A. fumigatus, C. neoformans and A. flavus. Its excellent antifungal activity was consistent with its excellent chitin synthase inhibition. Compound 5k and 5l against C. albicans were comparable with fluconazole, and they showed strong antifungal potency against A. flavus with MIC values of 0.07 mmol/L and 0.13 mmol/L resp. Compound 5m had similar MIC value against A. fumigatus to fluconazole. The phenomenon that compounds 5b, 5d and 5q that showed good enzymic inhibition didnt exert good antifungal activity, while compounds 5k, 5l and 5m that showed moderate chitin synthase inhibition exhibited excellent antifungal activity was discussed. Furthermore, the trial of drug combination showed that compounds had synergistic effects or additive effects with fluconazole against tested fungi which also verified that these designed compounds targeted different targets from that of fluconazole. Addnl., the antibacterial trial showed that all synthesized compounds had little potency against tested bacteria strains. These results indicated that the designed compounds were potential chitin synthase inhibitors and had selectively antifungal activities.

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 C6H12N2O, Name: Piperidine-4-carboxamide.

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

Kosak, Urban published the artcileN-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: Potential multifunctional anti-Alzheimer’s agents, Name: Piperidine-4-carboxamide, the publication is Bioorganic & Medicinal Chemistry (2017), 25(2), 633-645, database is CAplus and MEDLINE.

In the brains of patients with Alzheimer’s disease, the enzymic activities of butyrylcholinesterase (BChE) and monoamine oxidase B (MAO-B) are increased. While BChE is a viable therapeutic target for alleviation of symptoms caused by cholinergic hypofunction, MAO-B is a potential therapeutic target for prevention of neurodegeneration in Alzheimer’s disease. Starting with piperidine-based selective human (h)BChE inhibitors and propargylamine-based MAO inhibitors, the authors have designed, synthesized and biochem. evaluated a series of N-propargylpiperidines. All of these compounds inhibited hBChE with good selectivity over the related enzyme, acetylcholinesterase, and crossed the blood-brain barrier in a parallel artificial membrane permeation assay. The crystal structure of one of the inhibitors (compound 3) in complex with hBChE revealed its binding mode. Three compounds (4, 5, and 6) showed concomitant inhibition of MAO-B. Addnl., the most potent hBChE inhibitor 7 and dual BChE and MAO-B inhibitor 6 were non-cytotoxic and protected neuronal SH-SY5Y cells from toxic amyloid β-peptide species.

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, Name: Piperidine-4-carboxamide.

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

Kuroda, Shoichi published the artcileSynthesis and structure-activity relationship of C-phenyl D-glucitol (TP0454614) derivatives as selective sodium-dependent glucose cotransporter 1 (SGLT1) inhibitors, Recommanded Product: Piperidine-4-carboxamide, the publication is Chemical & Pharmaceutical Bulletin (2020), 68(7), 635-652, database is CAplus and MEDLINE.

Sodium-glucose cotransporter 1 (SGLT1) is the primary transporter for glucose absorption from the gastrointestinal tract. While C-Ph d-glucitol derivative SGL5213 has been reported to be a potent intestinal SGLT1 inhibitor for use in the treatment of type 2 diabetes, no SGLT1 selectivity was found in vitro (IC50 29 nM for hSGLT1 and 20 nM for hSGLT2). In this study we found a new method of synthesizing key intermediates 12 by a one-pot three-component condensation reaction and discovered C-Ph d-glucitol 41j (TP0454614), which has >40-fold SGLT1 selectivity in vitro (IC₅₀ 26 nM for hSGLT1 and 1101 nM for hSGLT2). The results of our study have provided new insights into the structure-activity relationships (SARs) of the SGLT1 selectivity of C-glucitol derivatives

Chemical & Pharmaceutical Bulletin 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

Savych, Olena published the artcileOne-Pot Parallel Synthesis of 5-(Dialkylamino)tetrazoles, COA of Formula: C6H12N2O, the publication is ACS Combinatorial Science (2019), 21(9), 635-642, database is CAplus and MEDLINE.

Two protocols for the combinatorial synthesis of 5-(dialkylamino)tetrazoles were developed. The best success rate (67%) was shown by the method that used primary and secondary amines, 2,2,2-trifluoroethylthiocarbamate, and sodium azide as the starting reagents. The key steps included the formation of unsym. thiourea, subsequent alkylation with 1,3-propane sultone and cyclization with azide anion. A 559-member aminotetrazole library was synthesized by this approach; the overall readily accessible (REAL) chem. space covered by the method exceeded 7 million feasible compounds

ACS Combinatorial Science 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

Bohlmann, Ferdinand published the artcileLupine alkaloids. XXVII. The effect of amino groups on the rate of solvolysis of esters, Recommanded Product: 1-Ethylpiperidin-3-ol, the publication is Chemische Berichte (1964), 97(6), 1619-24, database is CAplus.

cf. CA 61, 31542. The rates of solvolysis of a series of aminoalkyl azobenzenecarboxylates were investigated. The equatorial esters were always solvolyzed faster than the axial ones. The strong acceleration of the reaction by more remotely located amino and lactam groups is noteworthy. The rates of the solvolysis were determined for the azobenzenecarboxylates of the following alcs. (m.p., of ester, k × 10^-3 and k × 10^-4 of the hydrolysis at 19° with 0.2 and 0.02N KOH, resp., in 3:2 dioxane- H₂O, and k × 10^-3 and k × 10^-4 of the methanolysis at 19° with 0.2 and 0.02N NaOMe in MeOH given): Me₂NCH₂CH₂OH, 72.5°, -, 5.25, -, 9.30; iso-AmOH, 63°, -, 0.80, -, 1.40; CHC(CH₂)₃OH, -, -, 1.78, -, -; 6-piperidino-4-hexyn-1-ol, 60, 1.45, 1.40, -, 4.65; 6-piperidinopentanol, -, -, 0.90, -, 1.90; I, 81, 1.71, 1.12, -, 0.65; II, 106°, 1.40, 0.9, -, 1.11; III, 153°, -, 9.0, -, -; cyclohexanol, -, 0.15, -, -, 0.17; 1-methyl-4-piperidinol, -, 0.90, -, -, 1.28; 1-ethyl-3piperidinol, 69.5°, 1.83, -, -, 2.30; trans-2-dimethylaminocyclohexanol, 69°, 0.14, -, -, 0.20; 3-piperidinocyclohexanol, 124°, 0.50, -, -, 0.98; 4-dimethylaminocyclohexanol, 95-6°, 0.48, -, -, 0.98; IV, 145°, 0.73, -, 1.00, -; V, 137°, 0.042, -, 0.05, -; VI, 63°, 0.14, -, 0.013, -; VII, 110°, 0.092, -, â‰?.005, -; VIII, -, 0.74 -, 2.3, -; IX, 147°, 0.12, -, 0.2, -; X, -, 0.58, -, 0.17, -; XI, -, 0.27, -, 0.37, -; XII, -, 0.52, -, 1.8, -; XIII, 125-6°, 2.81, -, 4.4, -; XIV, 142°, 0.67, -, 0.09, -; 13a-hydroxylupinane, -, -, 0.12, -; 13a-hydroxysparteine (XV), -, -, -, 0.11, -, 17-oxo derivative of XV, -, -, -, 0.88, -; 13e-hydroxy-α-isolupinane, -, -, -, 0.77, -; 13e-hydroxy-17-oxolupinane, -, -, -, 10.0, -, 13e-hydroxylupinane, -, -, -, 1.6, -; 13e-hydroxysparteine, -, -, -, 1.5, -.

Chemische Berichte 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

Yadav, Nisha published the artcileTricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can specifically target bacterial DNA ligases and can distinguish them from human DNA ligase I, Name: Piperidine-4-carboxamide, the publication is Organic & Biomolecular Chemistry (2015), 13(19), 5475-5487, database is CAplus and MEDLINE.

DNA ligases are critical components for DNA metabolism in all organisms. NAD⁺-dependent DNA ligases (LigA) found exclusively in bacteria and certain entomopoxviruses are drawing increasing attention as therapeutic targets as they differ in their cofactor requirement from ATP-dependent eukaryotic homologs. Due to the similarities in the cofactor binding sites of the two classes of DNA ligases, it is necessary to find determinants that can distinguish between them for the exploitation of LigA as an anti-bacterial target. In the present endeavor, we have synthesized and evaluated a series of tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives, e.g. I [X = S, O, CH₂; R = 1-piperidinyl,, 4-hydroxy-1-piperidinyl, 1-pyrrolidinyl, etc.], for their ability to distinguish between bacterial and human DNA ligases. The in vivo inhibition assays that employed LigA deficient E. coli GR501 and S. typhimurium LT2 bacterial strains, rescued by ATP-dependent T4 DNA ligase or Mycobacterium tuberculosis NAD⁺-dependent DNA ligase (Mtb LigA), resp., showed that the compounds can specifically inhibit bacterial LigA. The in vitro enzyme inhibition assays using purified MtbLigA, human DNA ligase I & T4 DNA ligase showed specific inhibition of MtbLigA at low micromolar range. Our results demonstrate that tricyclic dihydrobenzoxazepine and tetracyclic indole derivatives can distinguish between bacterial and human DNA ligases by ∼5-folds. In silico docking and enzyme inhibition assays identified that the compounds bind to the cofactor binding site and compete with the cofactor. Ethidium bromide displacement and gel-shift assays showed that the inhibitors do not exhibit any unwanted general interactions with the substrate DNA. These results set the stage for the detailed exploration of this compound class for development as antibacterials.

Organic & Biomolecular 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 C10H14O2, Name: Piperidine-4-carboxamide.

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