Category: 33402-75-4

Sugimori, Akira; Tobita, Etsuo; Kumagai, Yasuyuki; Sato, Gen P. published the artcile< Multiple paths for photo-alkylation and -alkoxylation of 3-pyridinecarboxylic ester in alcohol. Simultaneous contribution of several kinds of excited states>, Electric Literature of 33402-75-4, the main research area is photochem alkylation alkoxylation pyridinecarboxylate.

UV irradiation of Me 3-pyridinecarboxylate (I) in acidic alc. solutions causes alkoxylation and alkylation at the pyridine ring. Photoalkylation occurs via several paths: 1) initiated by the triplet π-π* state; 2) initiated by the triplet n-π* state of the carbonyl moiety of the ester group; 3) initiated by an exciplex between a free-base form of I and a pyridinium form of I; and 4) promoted by Cl- ions. Photoalkoxylation originates from a singlet excited state of I. In the photoreactions of I in strongly acidic MeOH solutions acidified with H2SO4, 3 kinds of excited states (2 kinds of triplet states for alkylation and a singlet state for alkoxylation) contribute simultaneously.

Bulletin of the Chemical Society of Japan published new progress about Photochemical alkylation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Electric Literature of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dunn, A. D. published the artcile< Synthesis of new thiopyranopyridines>, Quality Control of 33402-75-4, the main research area is thiopyranopyridinecarboxylate; photochem bromination pyridinecarboxylate; bromomethylpyridinecarboxylate preparation substitution thioglycolate.

Thiopyranopyridinecarboxylates I and II (X, Y = CH, N; R = OH, NH2) are prepared from pyridine esters (e.g., III; R1 = Me, R2 = CO2Me; R1 = CO2Me, R2 = Me) and nitriles (e.g., III; R1 = Me, R2 = CN) by photochem. bromination, followed by substitution reaction of the resulting bromomethyl derivative with HSCH2CO2Me, and then base-induced intramol. cyclocondensation.

Journal fuer Praktische Chemie (Leipzig) published new progress about Cyclocondensation reaction, intramolecular. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Quality Control of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dolby, Jorgen; Dahlbom, Richard; Hasselgren, Karl H.; Nilsson, J. L. G. published the artcile< Bicyclic enamines. I. Rearrangement of a quaternary quinuclidine-3-carboxylic acid ester and total synthesis of gentianadine>, COA of Formula: C8H9NO2, the main research area is quinuclidinecarboxylic rearrangement; gentianadine alkaloid preparation; nicotinic lactone; enamines bicyclic.

Me 2,3-didehydroquinuclidine-3-carboxylate methiodide loses MeI and is rearranged to 4-(2-hydroxyethyl)-1-methyl-1,4,5,6-tetrahydronicotinic acid lactone when heated without solvent to its m.p. The structure of the lactone was confirmed by an independent synthesis which also involved the total synthesis of the alkaloid gentianadine.

Acta Chemica Scandinavica (1947-1973) published new progress about Rearrangement. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, COA of Formula: C8H9NO2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tresadern, Gary; Velter, Ingrid; Trabanco, Andres A.; Van den Keybus, Frans; Macdonald, Gregor J.; Somers, Marijke V. F.; Vanhoof, Greet; Leonard, Philip M.; Lamers, Marieke B. A. C.; Van Roosbroeck, Yves E. M.; Buijnsters, Peter J. J. A. published the artcile< [1,2,4]Triazolo[1,5-a]pyrimidine Phosphodiesterase 2A Inhibitors: Structure and Free-Energy Perturbation-Guided Exploration>, Formula: C8H9NO2, the main research area is triazolopyrimidine preparation selective PDE2A inhibitor; structure triazolopyrimidine inhibition phosphodiesterase selectivity; pharmacokinetics CYP inhibition BBB permeability triazolopyrimidine; free energy perturbation optimization triazolopyrimidine substituent phosphodiesterase inhibitor; crystal structure triazolopyrimidine complex phosphodiesterase 2A.

We describe the hit-to-lead exploration of a [1,2,4]triazolo[1,5-a]pyrimidine phosphodiesterase 2A (PDE2A) inhibitor arising from high-throughput screening. X-ray crystallog. enabled structure-guided design, leading to the identification of preferred substructural components. Further rounds of optimization used relative binding free-energy calculations to prioritize different substituents from the large accessible chem. space. The free-energy perturbation (FEP) calculations were performed for 265 putative PDE2A inhibitors, and 100 compounds were synthesized representing a relatively large prospective application providing unexpectedly active mols. with IC50’s from 2340 to 0.89 nM. Lead compound 46 originating from the FEP calculations showed PDE2A inhibition IC50 of 1.3 ± 0.39 nM, ~100-fold selectivity vs. other PDE enzymes, clean cytochrome P 450 profile, in vivo target occupancy, and promise for further lead optimization.

Journal of Medicinal Chemistry published new progress about Biological permeation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Formula: C8H9NO2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Wenkert, Ernest; Chang, Ching-Jer; Chawla, H. P. S.; Cochran, David W.; Hagaman, Edward W.; King, James C.; Orito, Kazuhiko published the artcile< General methods of synthesis of indole alkaloids. 14. Short routes of construction of yohimboid and ajmalicinoid alkaloid systems and their carbon-13 nuclear magnetic resonance spectral analysis>, Computed Properties of 33402-75-4, the main research area is akuammigine synthesis; alstonine tetrahydro synthesis; pseudoyohimbone synthesis; ajmalicine synthesis; indole alkaloid synthesis; configuration indole alkaloid; NMR carbon 13 alkaloid; yohimboid synthesis; ajmalicinoid synthesis.

Conceptually new schemes of synthesis of indole alkaloids are introduced. The yohimboid ring system is constructed by the sequential treatment of 1-tryptophyl-3-(β-oxobutyl)pyridinium bromide with base and acid. Hydrogenation of the product yields (±)-pseudoyohimbone (I). The ajmalicinoid ring system is formed by the exposure of 1-tryptophyl-3-acetylpyridinium bromide to NaCH(CO2Et)2 and then to acid, followed by hydrogenation. Subsequent reduction of dehydration of the products gives the racemates of the alkaloids tetrahydroalstonine (3α,20α-II), akuammigine (3β,20α-II) and isomers of ajmalicine (3α,20β-II). Complete C shift analyses of yohimboid and ajmalicinoid alkaloids of normal, pseudo, allo, and epiallo configuration were executed. Shifts of specific C are of stereochem. diagnostic value. A general shielding γ effect is observed for the interaction of C-H bonds with spatially rigid and directed electron pair orbitals.

Journal of the American Chemical Society published new progress about Alkaloids. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Computed Properties of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dolby, Jorgen; Dahlbom, Richard; Hasselgren, Karl H.; Nilsson, J. L. G. published the artcile< Bicyclic enamines. I. Rearrangement of a quaternary quinuclidine-3-carboxylic acid ester and total synthesis of gentianadine>, COA of Formula: C8H9NO2, the main research area is quinuclidinecarboxylic rearrangement; gentianadine alkaloid preparation; nicotinic lactone; enamines bicyclic.

Me 2,3-didehydroquinuclidine-3-carboxylate methiodide loses MeI and is rearranged to 4-(2-hydroxyethyl)-1-methyl-1,4,5,6-tetrahydronicotinic acid lactone when heated without solvent to its m.p. The structure of the lactone was confirmed by an independent synthesis which also involved the total synthesis of the alkaloid gentianadine.

Acta Chemica Scandinavica (1947-1973) published new progress about Rearrangement. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, COA of Formula: C8H9NO2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tresadern, Gary; Velter, Ingrid; Trabanco, Andres A.; Van den Keybus, Frans; Macdonald, Gregor J.; Somers, Marijke V. F.; Vanhoof, Greet; Leonard, Philip M.; Lamers, Marieke B. A. C.; Van Roosbroeck, Yves E. M.; Buijnsters, Peter J. J. A. published the artcile< [1,2,4]Triazolo[1,5-a]pyrimidine Phosphodiesterase 2A Inhibitors: Structure and Free-Energy Perturbation-Guided Exploration>, Formula: C8H9NO2, the main research area is triazolopyrimidine preparation selective PDE2A inhibitor; structure triazolopyrimidine inhibition phosphodiesterase selectivity; pharmacokinetics CYP inhibition BBB permeability triazolopyrimidine; free energy perturbation optimization triazolopyrimidine substituent phosphodiesterase inhibitor; crystal structure triazolopyrimidine complex phosphodiesterase 2A.

We describe the hit-to-lead exploration of a [1,2,4]triazolo[1,5-a]pyrimidine phosphodiesterase 2A (PDE2A) inhibitor arising from high-throughput screening. X-ray crystallog. enabled structure-guided design, leading to the identification of preferred substructural components. Further rounds of optimization used relative binding free-energy calculations to prioritize different substituents from the large accessible chem. space. The free-energy perturbation (FEP) calculations were performed for 265 putative PDE2A inhibitors, and 100 compounds were synthesized representing a relatively large prospective application providing unexpectedly active mols. with IC50’s from 2340 to 0.89 nM. Lead compound 46 originating from the FEP calculations showed PDE2A inhibition IC50 of 1.3 ± 0.39 nM, ~100-fold selectivity vs. other PDE enzymes, clean cytochrome P 450 profile, in vivo target occupancy, and promise for further lead optimization.

Journal of Medicinal Chemistry published new progress about Biological permeation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Formula: C8H9NO2.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Wenkert, Ernest; Chang, Ching-Jer; Chawla, H. P. S.; Cochran, David W.; Hagaman, Edward W.; King, James C.; Orito, Kazuhiko published the artcile< General methods of synthesis of indole alkaloids. 14. Short routes of construction of yohimboid and ajmalicinoid alkaloid systems and their carbon-13 nuclear magnetic resonance spectral analysis>, Computed Properties of 33402-75-4, the main research area is akuammigine synthesis; alstonine tetrahydro synthesis; pseudoyohimbone synthesis; ajmalicine synthesis; indole alkaloid synthesis; configuration indole alkaloid; NMR carbon 13 alkaloid; yohimboid synthesis; ajmalicinoid synthesis.

Conceptually new schemes of synthesis of indole alkaloids are introduced. The yohimboid ring system is constructed by the sequential treatment of 1-tryptophyl-3-(β-oxobutyl)pyridinium bromide with base and acid. Hydrogenation of the product yields (±)-pseudoyohimbone (I). The ajmalicinoid ring system is formed by the exposure of 1-tryptophyl-3-acetylpyridinium bromide to NaCH(CO2Et)2 and then to acid, followed by hydrogenation. Subsequent reduction of dehydration of the products gives the racemates of the alkaloids tetrahydroalstonine (3α,20α-II), akuammigine (3β,20α-II) and isomers of ajmalicine (3α,20β-II). Complete C shift analyses of yohimboid and ajmalicinoid alkaloids of normal, pseudo, allo, and epiallo configuration were executed. Shifts of specific C are of stereochem. diagnostic value. A general shielding γ effect is observed for the interaction of C-H bonds with spatially rigid and directed electron pair orbitals.

Journal of the American Chemical Society published new progress about Alkaloids. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Computed Properties of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics