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Organic Letters Oct 2006[structure: see text] Owing to the electronic nature of the bridging nitrogen atoms which can adopt different hybridizations and form various conjugations with the...
[structure: see text] Owing to the electronic nature of the bridging nitrogen atoms which can adopt different hybridizations and form various conjugations with the adjacent pyridine(s), methylazacalix[4]pyridine underwent conformation and cavity preorganization to highly selectively bind the Zn(2+) ion. Rigidification and coplanarity of the macrocyclic ring led to a great enhancement of fluorescence of the intrinsic fluorescent host molecule.
Topics: Fluorescence; Organometallic Compounds; Pyridines; Zinc
PubMed: 17020330
DOI: 10.1021/ol061928k -
Molecules (Basel, Switzerland) May 2004Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2- (benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2-...
Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2- (benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2- carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Work toward extending this methodology to the preparation of pyridine-fused selenium analogues of antioxidants is described.
Topics: Antioxidants; Free Radicals; Models, Chemical; Molecular Structure; Organoselenium Compounds; Photolysis; Pyridines; Reactive Oxygen Species; Selenium
PubMed: 18007447
DOI: 10.3390/90600472 -
Organic & Biomolecular Chemistry Jun 20154-(Dimethylamino)pyridine functioned as an excellent catalyst for iodolactonisation reactions of γ,δ-unsaturated carboxylic acids, affording γ-lactones, δ-lactones,...
4-(Dimethylamino)pyridine functioned as an excellent catalyst for iodolactonisation reactions of γ,δ-unsaturated carboxylic acids, affording γ-lactones, δ-lactones, or both under neutral conditions at room temperature. The effects of substrate structures on the iodolactonisation were investigated, and a catalytic mechanism is proposed.
Topics: Carboxylic Acids; Catalysis; Cyclization; Halogenation; Lactones; Methylamines; Pyridines
PubMed: 26009007
DOI: 10.1039/c5ob00806a -
European Journal of Medicinal Chemistry Jan 2010A series of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidines derivatives were synthesized using a convenient synthetic route. We evaluate the...
A series of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidines derivatives were synthesized using a convenient synthetic route. We evaluate the isosteric replacement of methyl groups in 4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-p-tolylpyrimidin-2-amine (compound 1) by trifluoromethyl groups and the isosteric substitution of the 2-methylimidazo[1,2-a]pyridin-3-yl scaffold by quinolin-4-yl or quinolin-3-yl moieties. The replacement of hydrogen by fluorine does not affect notably the cytotoxic activity and CDK inhibitor activity in this series. Quinolin-4-yl-substituted compound, 8, presents cytotoxic activity and is most effective and selective against CDK1/CycA than against CDK2/CycB. Compound 11, which has a quinolin-3-yl moiety is CDK inhibitor but presents null cytotoxic activity. Quinolin-4-yl-substituted compounds constitute a new lead of cytotoxic and CDK inhibitor compounds from which more compelling and selective inhibitors can be designed.
Topics: Antineoplastic Agents; Apoptosis; Cell Cycle; Cell Line, Tumor; Cyclin-Dependent Kinases; Humans; Inhibitory Concentration 50; Pyridines; Pyrimidines; Quinolines
PubMed: 19879023
DOI: 10.1016/j.ejmech.2009.10.002 -
Chemical Communications (Cambridge,... Aug 2013A facile and efficient protocol for palladium-catalyzed ortho-acylation of 2-aryl pyridines was developed. Note that this acylation utilized arylmethyl amines as new,...
A facile and efficient protocol for palladium-catalyzed ortho-acylation of 2-aryl pyridines was developed. Note that this acylation utilized arylmethyl amines as new, cheap and readily available acylation reagents and exhibited high regioselectivity for 2-aryl pyridines bearing a meta-substituent in the aryl ring moiety.
Topics: Acylation; Amines; Catalysis; Crystallography, X-Ray; Models, Molecular; Molecular Structure; Organometallic Compounds; Palladium; Pyridines
PubMed: 23629481
DOI: 10.1039/c3cc42106f -
Bioorganic & Medicinal Chemistry Letters Apr 2008A lead benzamide, bearing a cyanopyridyl moiety (3), was identified as a potent and low molecular weight histone deacetylase (HDAC) inhibitor. Various replacements of...
A lead benzamide, bearing a cyanopyridyl moiety (3), was identified as a potent and low molecular weight histone deacetylase (HDAC) inhibitor. Various replacements of the cyano group were explored at the C3-position, along with the exploration of solubility-enhancing groups at the C5-position. It was determined that cyano substitution at the C3-position of the pyridyl core, along with a methylazetidinyl substituent at the C5-position yielded optimal HDAC1 inhibition and anti-proliferative activity in HCT-116 cells.
Topics: Animals; Drug Design; Enzyme Inhibitors; Histone Deacetylase Inhibitors; Histone Deacetylases; Humans; Molecular Structure; Pyridines; Rats; Structure-Activity Relationship
PubMed: 18378451
DOI: 10.1016/j.bmcl.2008.03.058 -
European Journal of Medicinal Chemistry Sep 2017Acarbose, miglitol, and voglibose are the inhibitors of α-glucosidase enzyme and being clinically used for the management of type-II diabetes mellitus. However, many...
Acarbose, miglitol, and voglibose are the inhibitors of α-glucosidase enzyme and being clinically used for the management of type-II diabetes mellitus. However, many adverse effects are also associated with them. So, the development of new therapeutic agents is an utmost interest in medicinal chemistry research. Current study is based on the identification of new α-glucosidase inhibitors. For that purpose, hydrazinyl arylthiazole based pyridine derivatives 1-39 were synthesized via two step reaction and fully characterized by spectroscopic techniques EI-MS, HREI-MS, H-, and C NMR. However, stereochemistry of the iminic bond was confirmed by NOESY. All compounds were subjected to in vitro α-glucosidase inhibitory activity and found many folds active (IC = 1.40 ± 0.01-236.10 ± 2.20 μM) as compared to the standard acarbose having IC value of 856.45 ± 5.60 μM. A limited structure-activity relationship was carried out in order to make a presumption about the substituent's effect on inhibitory activity which predicted that substituents of more negative inductive effect played important role in the activity as compared to the substituents of less negative inductive effect. However, in order to have a good understanding of ligand enzyme interactions, molecular docking study was also conducted. In silico study was confirmed that substituents like halogens (Cl) and nitro (NO) which have negative inductive effect were found to make important interactions with active site residues.
Topics: Dose-Response Relationship, Drug; Glycoside Hydrolase Inhibitors; Molecular Docking Simulation; Molecular Structure; Pyridines; Saccharomyces cerevisiae; Structure-Activity Relationship; Thiazoles; alpha-Glucosidases
PubMed: 28672278
DOI: 10.1016/j.ejmech.2017.06.041 -
Journal of Fluorescence Mar 2015A two new compounds with potential biologically active were synthesized: ethyl 4-(2H-4,6-dimethyl-3-oxo-2,3-dihydroisothiazolo [5,4-b] pyridin-2-yl) butanoate and ethyl...
A two new compounds with potential biologically active were synthesized: ethyl 4-(2H-4,6-dimethyl-3-oxo-2,3-dihydroisothiazolo [5,4-b] pyridin-2-yl) butanoate and ethyl 4-(2H-4,6-dimethyl-2,3-dihydroisothiazolo [5,4-b] pyridin-3-yloxy) butanoate. The structures of all of the newly formed compounds were identified by elemental analysis, FTIR and (1)H NMR. Their optical properties were studied in ethanol and n-hexane by UV-Vis absorption and fluorescence spectroscopy. The ground-state and excited-state properties were investigated using the density functional theory (DFT) and the time-dependent density functional theory (TDDFT) methods. The results showed differences between emission spectra in ethanol and n-hexane solution (solvatochromism) for both new compounds.
Topics: Chemistry Techniques, Synthetic; Esters; Pyridines; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Thiazoles
PubMed: 25612854
DOI: 10.1007/s10895-015-1504-6 -
Organic Letters Dec 2013A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with...
A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with ketone oxime esters.
Topics: Catalysis; Copper; Cyclization; Esters; Hydrogenation; Molecular Structure; Oximes; Pyridines
PubMed: 24261576
DOI: 10.1021/ol403105p -
Journal of Combinatorial Chemistry Jul 2010A simple and efficient method for the combinatorial synthesis of highly substituted thiopyrano[3,4-b]pyridin-5(4H)-one, thiopyrano[3,4-b]quinoline-4,6(3H,5H)-dione,...
A simple and efficient method for the combinatorial synthesis of highly substituted thiopyrano[3,4-b]pyridin-5(4H)-one, thiopyrano[3,4-b]quinoline-4,6(3H,5H)-dione, dithiopyrano[3,4-b:4',3'-e]pyridine-4,6(1H,3H)-dione, and pyrazolo[3,4-b]thiopyrano[4,3-e]pyridin-5(1H)-one derivatives has been developed. The synthesis was achieved via one-pot multicomponent reaction of aromatic aldehyde, 2H-thiopyran-3,5(4H,6H)-dione and enamine (such as the derivatives of amine and 1,3-dicarbonyl compounds and 3-methyl-1-phenyl-1H-pyrazol-5-amine) in glacial acetic acid. This procedure features short reaction time, generally good to excellent yields, easily available starting materials, and operational simplicity. This chemistry provides an efficient and promising synthetic strategy to diversity-oriented construction of the thiopyrano[3,4-b]pyridine skeleton.
Topics: Combinatorial Chemistry Techniques; Crystallography, X-Ray; Models, Molecular; Molecular Structure; Pyrans; Pyridines; Pyridones; Small Molecule Libraries
PubMed: 20443618
DOI: 10.1021/cc100017f