Tag: M.W=100-150

Gaonkar, Supreet published the artcileExploring the potential of newly synthesized 4-methyl-6-morpholino-pyrimidine derivatives as antiproliferative agents, Recommanded Product: Piperidine-4-carboxamide, the publication is New Journal of Chemistry (2018), 42(4), 2790-2803, database is CAplus.

In view of exploring the potential of pyrimidine derivatives as anticancer agents, a series of 4-methyl-6-morpholinopyrimidine derivatives was synthesized and characterised by NMR (¹H & ¹³C), SC-XRD and mass spectral anal. The in vitro anticancer activity of these compounds was investigated using different human cancer cell lines, namely HeLa (cervix), NCI-H460 (lung), MCF-7 (breast), HepG2 (liver) and IMR-32 (brain). Compounds 4c and 5h exhibited potent anticancer activity in a dose-dependent manner as compared to other derivatives, with IC₅₀ values of 5.88 ± 1.22 and 6.11 ± 2.12 μM on HeLa and NCI-H460, cells resp. The inhibitory effect of 4c and 5h on cancer cell proliferation was shown to be a consequence of reactive oxygen species (ROS) generation and subsequent induction of cellular apoptosis, as evidenced by an increase in hypodiploid (subG1) population, early apoptotic cell population, caspase-3/7 activity, loss of mitochondrial membrane potential and degradation of nuclear DNA. Furthermore, mol. docking studies revealed that 4c and 5h compounds bind to the ATP binding pocket of the mammalian target of rapamycin (mTOR). Based on our results, we conclude that 4-methyl-6-morpholinopyrimidine derivatives prevent cancer cell proliferation by inducing apoptosis and thus have potential to be further explored for anticancer properties.

New Journal of 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

Galvez, Alberto Osuna published the artcileChemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions, SDS of cas: 39546-32-2, the publication is Journal of the American Chemical Society (2017), 139(5), 1826-1829, database is CAplus and MEDLINE.

Amides, imides, acylguanidines, an acylcarbamate, an acylsulfonamide, and acylureas were prepared chemoselectively by reaction of aroyltrifluoroborates with primary amines using dichlorodimethylhydantoin or with primary amides, tert-Bu carbamate, guanidines, ureas, or methanesulfonamide using trichlorocyanuric acid (TCA) in buffered aqueous THF at pH 3; chemoselective acylation of primary amines and amides occurred in the presence of alcs., carboxylic acids, and even secondary amines. Streptomycin, gentamicin C₁, and polymyxin B were chemoselectively acylated using the method, showing its potential utility in later-stage functionalization reactions.

Journal of the American 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, SDS of cas: 39546-32-2.

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

Kennedy, Nicole M. published the artcileOptimization of a Series of Mu Opioid Receptor (MOR) Agonists with High G Protein Signaling Bias, Category: piperidines, the publication is Journal of Medicinal Chemistry (2018), 61(19), 8895-8907, database is CAplus and MEDLINE.

While mu opioid receptor (MOR) agonists are especially effective as broad-spectrum pain relievers, it has been exceptionally difficult to achieve a clear separation of analgesia from many problematic side effects. Recently, MOR agonists that induce minimal βarrestin-mediated signaling were extensively investigated because MOR agonist-treated βarrestin2 knockout mice were found to display enhanced antinociceptive effects with significantly less respiratory depression and tachyphylaxis. Substantial data now exists to support the premise that G protein signaling biased MOR agonists can be effective analgesic agents. It was recently shown that, within a chem. series, the degree of bias correlates linearly with the magnitude of the respiratory safety index. Herein, the synthesis and optimization of (piperidinyl)benzimidazolone MOR agonists I (R¹ = H, 4-Cl, 5-Me, 5-CN, 5,6-Cl₂, etc.; R² = H, Me; R³ = Ph, 2-ClC₆H₄, 2-F-4-BrC₆H₃, etc.) and analogs that display a wide range of bias (G/βarr2) is described. The structural features affecting potency and maximizing bias were identified and many compounds were shown to have desirable properties, such as long half-lives and high brain penetration.

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, Category: piperidines.

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

Fujimoto, James M. published the artcileBarbiturate metabolism as affected by certain agents acting on the liver, Name: 1-Ethylpiperidin-3-ol, the publication is Journal of Pharmacology and Experimental Therapeutics (1960), 139-43, database is CAplus and MEDLINE.

cf. Federation Proc. 17, 369(1958). N-Ethyl-3-piperidyl diphenylacetate (Dactil, JB-305) and benzilate (JB-371), N-methyl-3-piperidyl diphenylcarbamate (JB-371) (I), and β-phenylisopropylhydrazine (Catron, JB-516) (II) prolonged the sleeping time for certain barbiturates in mice, the effect varying with the particular barbiturate selected. Studies employing the whole-body concentration of hexobarbital, isolated rat liver perfusions, and measurements of bromsulfalein-retention point to effects of the prolonging agents on drug metabolites as a major factor in explaining the observed effects. In comparing the inhibitory spectrum of activity of these agents on drug metabolism I was found relatively most specific and II least specific.

Journal of Pharmacology and Experimental Therapeutics 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, Name: 1-Ethylpiperidin-3-ol.

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

Karicherla, Venumanikanta published the artcileA Simple and Commercially Viable Process for Improved Yields of Metopimazine, a Dopamine D₂-Receptor Antagonist, Category: piperidines, the publication is Organic Process Research & Development (2017), 21(5), 720-731, database is CAplus.

An efficient, practical, and com. viable manufacturing process was developed with ≥99.7% purity and 31% overall yield (including four chem. reactions and one recrystallization) for an active pharmaceutical ingredient, called Metopimazine I, an antiemetic drug used to prevent emesis during chemotherapy. The development of two in situ, one-pot methods in the present synthetic route helped to improve the overall yield of I (31%) compared with earlier reports (<15%). For the first time, characterization data of API I, intermediates, and also possible impurities are presented. The key process issues and challenges were addressed effectively and achieved successfully.

Organic Process Research & Development 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, Category: piperidines.

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

Pasqualetto, Gaia published the artcileLigand-based rational design, synthesis and evaluation of novel potential chemical chaperones for opsin, COA of Formula: C6H12N2O, the publication is European Journal of Medicinal Chemistry (2021), 113841, database is CAplus and MEDLINE.

Inherited blinding diseases retinitis pigmentosa (RP) and a subset of Leber’s congenital amaurosis (LCA) are caused by the misfolding and mistrafficking of rhodopsin mols., which aggregate and accumulate in the endoplasmic reticulum (ER), leading to photoreceptor cell death. One potential therapeutic strategy to prevent the loss of photoreceptors in these conditions is to identify opsin-binding compounds that act as chem. chaperones for opsin, aiding its proper folding and trafficking to the outer cell membrane. Aiming to identify novel compounds with such effect, a rational ligand-based approach was applied to the structure of the visual pigment chromophore, 11-cis-retinal, and its locked analog 11-cis-6mr-retinal. Following mol. docking studies on the main chromophore binding site of rhodopsin, 49 novel compounds, e.g., I, were synthesized according to optimized one-to seven-step synthetic routes. These agents were evaluated for their ability to compete for the chromophore binding site of opsin, and their capacity to increase the trafficking of the P23H opsin mutant from the ER to the cell membrane. Different new mols. displayed an effect in at least one assay, acting either as chem. chaperones or as stabilizers of the 9-cis-retinal-rhodopsin complex. These compounds could provide the basis to develop novel therapeutics for RP and LCA.

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 C6H12N2O, COA of Formula: C6H12N2O.

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

Dalacroix, A. published the artcileUse of experience plans associated with direct methods for optimization in chemometry, Name: 1-Ethylpiperidin-3-ol, the publication is Analusis (1996), 24(1), M22-M25, database is CAplus.

Experience plans are discussed in connection with chemometry for statistical optimization of anal. methods and reaction processes, including methods for colorimetric dosing of ergotamine, the process of chlorination of ethyl-1-hydroxy-3-piperidine, generally spectrophotometric methods of anal., the process of urethane prepolymer synthesis, and the process of n-thymol synthesis by m-cresol alkylation.

Analusis 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, Name: 1-Ethylpiperidin-3-ol.

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

Wohl, A. published the artcileArecolone and N-methyl-ω-amina-β-pipecoline, Recommanded Product: (1-Methylpiperidin-3-yl)methanamine, the publication is Justus Liebigs Annalen der Chemie (1924), 139-49, database is CAplus.

Condensation of (EtO)₂CHCH₂CH₂NH₂ and HCHO gives an anhydro-base, [CH₂:NCH₂CH₂CH(OEt)₂]_n, oil which decomposes on distilling in vacuo and reduces Fehling solution and NH₄OH-AgNO₃. A modification of Blaise and Maire’s method for CH₂:CHAc (C. A. 2, 1824) is given, the yields being 25-35%. The residue, treated with AcCl, gives the compound, C₉H₁₄O₅, m. 85°. CH₂: CHAc does not appear to condense with (EtO)₂CHCH₂NH₂ to give a definite compound With (EtO)₂CHCH₂CH₂NHMe, there results the compound, (EtO)₂CHCH₂CH₂NMeCH₂CH₂Ac, light yellow oil, which cannot be distd, in vacuum but with concentrated HCl in a cooling mixture it yields 40-60% of the HCl salt, m. 204°, of arecolone (N-methyl-Δ³-tetrahydropyridine β-Me ketone), light yellow oil, b_0.01 80-2°, reduces acid KMnO₄ in the cold. HBr salt, m. 223°. Semicarbazone, m. 219° (decomposition); HCl salt, m. 233°. Arecaidine aldehyde oxime, m. 130°. Reduction with Na-Hg gives 50% of N-methyl-ω-amino-β-pipecoline, b₁₂ 116-8°; Bz derivative, m. 161-2°.

Justus Liebigs Annalen der Chemie 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 C18H35NO, Recommanded Product: (1-Methylpiperidin-3-yl)methanamine.

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

Li, Jingjing published the artcileFe/HZSM-5 catalyzed liquefaction of cellulose assisted by glycerol, Safety of Piperidine-4-carboxamide, the publication is Catalysis Communications (2021), 106268, database is CAplus.

Fe/HZSM-5 catalyst was prepared by the impregnation method and employed for the liquefaction of cellulose at 350°C for 30 min. Iron changed the surface acidity of HZSM-5 and provided stronger acid sites. Fe/HZSM-5 improved the yield of bio-oil, and the coke formation was inhibited compared to HZSM-5 alone. The presence of glycerol and Fe/HZSM-5 promoted both the hydrodeoxygenation (HDO) and aromatization reactions. Ketones yields decreased from 29% to 7%, and the content of aromatics and furans increased significantly. The possible hydrogen supply mechanism of glycerol and the route of cellulose liquefaction were proposed.

Catalysis 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, Safety of Piperidine-4-carboxamide.

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

Poehner, Ina published the artcileMultitarget, Selective Compound Design Yields Potent Inhibitors of a Kinetoplastid Pteridine Reductase 1, Recommanded Product: Piperidine-4-carboxamide, the publication is Journal of Medicinal Chemistry (2022), 65(13), 9011-9033, database is CAplus and MEDLINE.

The optimization of compounds with multiple targets is a difficult multidimensional problem in the drug discovery cycle. Here, we present a systematic, multidisciplinary approach to the development of selective antiparasitic compounds Computational fragment-based design of novel pteridine derivatives along with iterations of crystallog. structure determination allowed for the derivation of a structure-activity relationship for multitarget inhibition. The approach yielded compounds showing apparent picomolar inhibition of T. brucei pteridine reductase 1 (PTR1), nanomolar inhibition of L. major PTR1, and selective submicromolar inhibition of parasite dihydrofolate reductase (DHFR) vs. human DHFR. Moreover, by combining design for polypharmacol. with a property-based on-parasite optimization, we found three compounds that exhibited micromolar EC₅₀ values against T. brucei brucei while retaining their target inhibition. Our results provide a basis for the further development of pteridine-based compounds, and we expect our multitarget approach to be generally applicable to the design and optimization of anti-infective agents.

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, Recommanded Product: Piperidine-4-carboxamide.

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