Category: 71255-09-9

Roy, Patrick J. published the artcileThe Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles, HPLC of Formula: 71255-09-9, the main research area is pyrrolo pyridine azaindole preparation cyclization thermolysis pyridinyl azido propenoate; azido pyridine acrylate preparation thermal cyclization Hemetsberger Knittel; Hemetsberger Knittel synthesis azaindole thermolysis cyclization template.

A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a min. temperature The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chem. diversity.

Synthesis published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, HPLC of Formula: 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trecourt, Francois published the artcileSynthesis of diazaxanthones: 5H-pyrano[2,3b:6,5-b’]dipyridin-5-one and 5H-thiopyrano[2,3-b:6,5-b’]dipyridin-5-one, Computed Properties of 71255-09-9, the main research area is pyranodipyridinone; thiopyranodipyridinone; formylation bromopyridine; pyridinecarboxaldehyde conformation.

The title compds (I; X = O, S, resp.) were prepared in 5 and 6 steps, resp., from 3-bromo-2-chloropyridine; yields were excellent. The CO bridge of the diazaxanthones was formed by coupling the aldehydes II (X = O) with 3-lithio-2-methoxypyridine and II (X = S) with 3-lithio-2-(methylthio)pyridine followed by oxidation of the resulting benzylic alc. The other bridge was formed by coupling the 2 ether or sulfide functions with pyridinium-HCl at ∼220°. The conformations of II (X = O, S) are discussed. II (X = O, S) were prepared by treatment of the 3-bromo analogs with BuLi and HCO2Et. I are the 1st reported xanthone-like heterocycles with 2 pyridine rings condensed to the 4-pyrone or -thiopyrone ring.

Journal of Chemical Research, Synopses published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Computed Properties of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Roy, Patrick J. published the artcileThe Hemetsberger-Knittel synthesis of substituted 5-, 6-, and 7-azaindoles, HPLC of Formula: 71255-09-9, the main research area is pyrrolo pyridine azaindole preparation cyclization thermolysis pyridinyl azido propenoate; azido pyridine acrylate preparation thermal cyclization Hemetsberger Knittel; Hemetsberger Knittel synthesis azaindole thermolysis cyclization template.

A series of substituted 5-, 6-, and 7-azaindoles were prepared via the Hemetsberger-Knittel reaction. In general, better yields were obtained at higher temperatures and shorter reaction times than required for the formation of the analogous indoles, and in some cases, only decomposition occurred below a min. temperature The resulting templates offer up to five sites for subsequent functionalization to allow a wide range of chem. diversity.

Synthesis published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, HPLC of Formula: 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trecourt, Francois published the artcileSynthesis of diazaxanthones: 5H-pyrano[2,3b:6,5-b’]dipyridin-5-one and 5H-thiopyrano[2,3-b:6,5-b’]dipyridin-5-one, Computed Properties of 71255-09-9, the main research area is pyranodipyridinone; thiopyranodipyridinone; formylation bromopyridine; pyridinecarboxaldehyde conformation.

The title compds (I; X = O, S, resp.) were prepared in 5 and 6 steps, resp., from 3-bromo-2-chloropyridine; yields were excellent. The CO bridge of the diazaxanthones was formed by coupling the aldehydes II (X = O) with 3-lithio-2-methoxypyridine and II (X = S) with 3-lithio-2-(methylthio)pyridine followed by oxidation of the resulting benzylic alc. The other bridge was formed by coupling the 2 ether or sulfide functions with pyridinium-HCl at ∼220°. The conformations of II (X = O, S) are discussed. II (X = O, S) were prepared by treatment of the 3-bromo analogs with BuLi and HCO2Et. I are the 1st reported xanthone-like heterocycles with 2 pyridine rings condensed to the 4-pyrone or -thiopyrone ring.

Journal of Chemical Research, Synopses published new progress about Cyclization. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Computed Properties of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sidhu, Preetpal S. published the artcileDevelopment of Novel Vitamin D Receptor-Coactivator Inhibitors, Safety of 2-Methoxynicotinaldehyde, the main research area is novel vitamin D receptor coactivator inhibitor; 3-indolylmethanamines; CAMP; CYP24A1; HL60; VDR; Vitamin D receptor; apoptosis; fluorescence polarization; high throughput screening; steroid receptor coactivator.

Nuclear receptor coregulators are master regulators of transcription and selectively interact with the vitamin D receptor (VDR) to modulate cell differentiation, cell proliferation, and calcium homeostasis. Herein, we report the syntheses and evaluation of highly potent and selective VDR-coactivator inhibitors based on a recently identified 3-indolylmethanamine scaffold. The most active compound, PS121912, selectively inhibited VDR-mediated transcription among eight other nuclear receptors tested. PS121912 is also selectively disrupting the binding between VDR and the third nuclear receptor interaction domain of the coactivator SRC2. Genetic studies revealed that PS121912 behaves like a VDR antagonist by repressing 1,25-(OH)2D3 activated gene transcription. In addition, PS121912 induced apoptosis in HL-60.

ACS Medicinal Chemistry Letters published new progress about Homo sapiens. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Safety of 2-Methoxynicotinaldehyde.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pagano, Nicholas published the artcileAn integrated chemical biology approach reveals the mechanism of action of HIV replication inhibitors, Computed Properties of 71255-09-9, the main research area is dihydropyrimidinone derivative preparation antiviral HIV replication reverse transcriptase inhibitor; Dihydropyrimidinone; Flow chemistry; HIV; Microreactors; Multistep synthesis; NNRTI; Resistant virus activity.

Continuous flow (microfluidic) chem. was employed to prepare a small focused library of dihydropyrimidinone (DHPM) derivatives Compounds in this class have been reported to exhibit activity against the human immunodeficiency virus (HIV), but their mol. target had not been identified. The authors tested the initial set of DHPMs in phenotypic assays providing a hit (4-(2-(4-(3-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)thiazol-4-yl)benzonitrile (1i)) that inhibited the replication of the human immunodeficiency virus HIV in cells. Flow chem.-driven optimization of 1i led to the identification of HIV replication inhibitors such as (4-(2-(4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)thiazol-4-yl)benzonitrile (1l)) with cellular potency comparable with the clin. drug nevirapine (NVP). Mechanism of action (MOA) studies using cellular and biochem. assays coupled with 3D fingerprinting and in silico modeling demonstrated that these drug-like probe compounds exert their effects by inhibiting the viral reverse transcriptase polymerase (RT). This led to the design and synthesis of the novel DHPM (3-methyl-4-(2-(6-methyl-4-(1-methyl-1H-indol-2-yl)-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)thiazol-4-yl)benzonitrile (1at)) that inhibits the replication of drug resistant strains of HIV. The authors’ work demonstrates that combining flow chem.-driven analog refinement with phenotypic assays, in silico modeling and MOA studies is a highly effective strategy for hit-to-lead optimization applicable to the discovery of future therapeutic agents.

Bioorganic & Medicinal Chemistry published new progress about AIDS (disease). 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Computed Properties of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wells, Jeffrey L. published the artcileOn the electrophilic reactivities of α-carbonyl heterocycles and arenes, Quality Control of 71255-09-9, the main research area is heterocyclic aldehyde hemi acetal formation electrophilic reactivity LUMO.

A series of heterocyclic aldehydes and substituted benzaldehydes were studied for their tendencies to form hemiacetal products with methanol. The equilibrium ratios were compared with DFT calculated MO levels and the hemi-acetal content was found to correlate roughly to the energy level of the lowest unoccupied MOs (LUMOs). Hemi-acetal formation is enhanced by intramol. hydrogen bonds and diminished by steric effects.

Pharma Chemica published new progress about Acid catalysis. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Quality Control of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hansen, Martin published the artcileSynthesis and pharmacological evaluation of N-benzyl substituted 4-bromo-2,5-dimethoxyphenethylamines as 5-HT2A/2C partial agonists, Computed Properties of 71255-09-9, the main research area is bromodimethoxy phenethyl amine preparation 5HT2A 5HT2C agonist; 5-HT(2A) agonists; N-Benzyl phenethylamines; Selectivity; Serotonin; Structure activity relations.

N-Benzyl substitution of phenethylamine 5-HT2A receptor agonists has dramatic effects on binding affinity, receptor selectivity and agonist activity. In this paper we examine how affinity for the 5-HT2A/2C receptors are influenced by N-benzyl substitution of 4-bromo-2,5-dimethoxyphenethylamine derivatives Special attention is given to the 2′ and 3′-position of the N-benzyl as such compounds are known to be very potent. We found that substitutions in these positions are generally well tolerated. The 2′-position was further examined using a range of substituents to probe the hydrogen bonding requirements for optimal affinity and selectivity, and it was found that small changes in the ligands in this area had a profound effect on their affinities. Furthermore, two ligands that lack a 2′-benzyl substituent were also found to have high affinity contradicting previous held notions. Several high-affinity ligands were identified and assayed for functional activity at the 5-HT2A and 5-HT2C receptor, and they were generally found to be less efficacious agonists than previously reported N-benzyl phenethylamines.

Bioorganic & Medicinal Chemistry published new progress about 5-HT2A agonists. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Computed Properties of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Radix, Sylvie published the artcileA Journey through Hemetsberger-Knittel, Leimgruber-Batcho and Bartoli Reactions: Access to Several Hydroxy 5- and 6-Azaindoles, Application In Synthesis of 71255-09-9, the main research area is azaindole preparation Hemetsberger Knittel Bartoli Leimgruber Batcho reaction.

The preparation of various 5- and 6-azaindoles, heterocyclic structures e.g., I that are frequently part of mols. in clin. development, and their monohydroxy analogs were described. Different strategies, relying on the de novo pyrrole ring formation, were investigated and, Hemetsberger-Knittel, Bartoli and Leimgruber-Batcho approaches, 4- and 7-monohydroxy 5- and 6-azaindoles e.g., I were obtained. The crucial introduction of the oxygen atom was carried out from halogen derivatives, using nucleophilic substitution reactions under basic conditions with or without a copper catalyst. Some preliminary oxidation reactions have shown that it was yet not possible to synthesize the azaquinone indole structure from monohydroxy azaindole, using mol. oxygen in the presence of salcomine as a catalyst.

Helvetica Chimica Acta published new progress about Bartoli reaction. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Application In Synthesis of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Zhang, Guiping published the artcileDiscovery of N-substituted (2-phenylcyclopropyl)methylamines as functionally selective serotonin 2C receptor agonists for potential use as antipsychotic medications, Application In Synthesis of 71255-09-9, the main research area is phenylcyclopropylmethylamine preparation serotonin 2C receptor agonist antipsychotic.

A series of N-substituted (2-phenylcyclopropyl)methylamines were designed and synthesized, with the aim of finding serotonin 2C (5-HT2C)-selective agonists with a preference for Gq signaling. A number of these compounds exhibit 5-HT2C selectivity with a preference for Gq-mediated signaling compared with β-arrestin recruitment. Furthermore, the N-Me compound I•HCl, which displayed an EC50 of 23 nM in the calcium flux assay while showing no β-arrestin recruitment activity, is the most functionally selective 5-HT2C agonist reported to date. The N-benzyl compound II•HCl, which showed an EC50 of 24 nM at the 5-HT2C receptor, is fully selective over the 5-HT2B receptor. In an amphetamine-induced hyperactivity model, compound II showed significant antipsychotic-drug-like activity. These compounds shed light on the role of functional selectivity at the 5-HT2C receptor with respect to antipsychotic activity.

Journal of Medicinal Chemistry published new progress about 5-HT2C agonists. 71255-09-9 belongs to class pyridine-derivatives, name is 2-Methoxynicotinaldehyde, and the molecular formula is C7H7NO2, Application In Synthesis of 71255-09-9.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem