54950-20-8

Usage

Chemical Properties

white to pink-brownish crystalline powder

InChI:InChI=1/C9H9NO3/c1-13-9(12)5-8(11)7-3-2-4-10-6-7/h2-4,6H,5H2,1H3

Upstream product

• 350-03-8 methyl-3-pyridylketone 
• 616-38-6 carbonic acid dimethyl ester 
• 59-67-6 nicotinic acid 
• 38330-80-2 monomethyl monopotassium malonate 
• 75399-10-9 (Z)-3-Hydroxy-3-pyridin-3-yl-acrylic acid methyl ester 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 1268849-82-6 2-(3-(benzyloxy)phenyl)-6-(pyridin-3-yl)pyrimidin-4-ol 
• 56775-88-3 Zimelidine 
• 56775-89-4 (E)-3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine 
• 77470-73-6 (Z)-3-(4-bromophenyl)-3-(3-pyridinyl)prop-2-en-1-ol 
• 91671-06-6 (E)-3-(4-bromophenyl)-3-(3-pyridinyl)prop-2-en-1-ol 
• 70263-44-4 (Z)-3-(4-bromophenyl)-3-(3-pyridyl) allyl chloride 
• 1426444-75-8 methyl 2-phenyl-5-(pyridin-3-yl)oxazole-4-carboxylate 
• 1426444-78-1 2-(2-phenyl-5-(pyridin-3-yl)oxazol-4-yl)acetonitrile 
• 1426444-77-0 4-(chloromethyl)-2-phenyl-5-(pyridin-3-yl)oxazole 
• 1426444-76-9 (2-phenyl-5-(pyridin-3-yl)oxazol-4-yl)methanol 
• 1361236-13-6 1-methyl-2-phenyl-5-(pyridin-3-yl)-1,2-dihydropyrazol-3-one 
• 1361236-22-7 1-methyl-3-oxo-2-phenyl-5-(pyridin-3-yl)-2,3-dihydro-1H-pyrazole-4-carbaldehyde 
• 1361236-30-7 1-methyl-3-oxo-2-phenyl-5-(pyridin-3-yl)-2,3-dihydro-1H-pyrazole-4-carboxylic acid 

Relevant academic research and scientific papers

An Alternate Synthesis of Deethylvincadifformine

A synthesis of 20-deethylvincadifformine from methyl nicotinylacetate is described.The reaction scheme involved a fast construction of the pentacyclic nucleus of the Aspidosperma alkaloids and the early incorporation of the 16-carbomethoxy group common to these bases.

PHOSPHORUS-CONTAINING PRODRUGS OF GEMCITABINE

This invention relates to phosphorus-containing prodrugs of gemcitabine and their use in the treatment of cancer and viral infectious diseases. Compared with the parent drug (i.e., Gemcitabine), the prodrugs of present invention show a significant overall

NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS

The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.

Quinone-Fused Pyrazoles through 1,3-Dipolar Cycloadditions: Synthesis of Tricyclic Scaffolds and in vitro Cytotoxic Activity Evaluation on Glioblastoma Cancer Cells

A novel and straightforward synthesis of highly substituted isoquinoline-5,8-dione fused tricyclic pyrazoles is reported. The key step of the synthetic sequence is a regioselective, Ag2CO3 promoted, 1,3-dipolar cycloaddition of C-heteroaryl-N-aryl nitrilimines and substituted isoquinoline-5,8-diones. The broad functional group tolerability and mild reaction conditions were found to be suitable for the preparation of a small library of compounds. These scaffolds were designed to interact with multiple biological residues, and two of them, after brief synthetic elaborations, were analyzed by molecular docking studies as potential anticancer drugs. In vitro studies confirmed the potent anticancer effects, showing promising IC50 values as low as 2.5 μm against three different glioblastoma cell lines. Their cytotoxic activity was finally positively correlated to their ability to inhibit PI3K/mTOR kinases, which are responsible for the regulation of diverse cellular processes in human cancer cells.

The guareschi pyridine scaffold as a valuable platform for the identification of selective PI3K inhibitors

A novel series of 4-aryl-3-cyano-2-(3-hydroxyphenyl)-6-morpholino-pyridines have been designed as potential phosphatidylinositol-3-kinase (PI3K) inhibitors. The compounds have been synthesized using the Guareschi reaction to prepare the key 4-aryl- 3-cyano-2,6-dihydroxypyridine intermediate. A different selectivity according to the nature of the aryl group has been observed. Compound 9b is a selective inhibitor against the PI3Kα isoform, maintaining a good inhibitory activity. Docking studies were also performed in order to rationalize its profile of selectivity.

Structure-based design of novel class II c-Met inhibitors: 2. SAR and kinase selectivity profiles of the pyrazolone series

As part of our effort toward developing an effective therapeutic agent for c-Met-dependent tumors, a pyrazolone-based class II c-Met inhibitor, N-(4-((6,7-dimethoxyquinolin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-pyrazole-4-c

Preparation and evaluation of trisubstituted pyrimidines as phosphatidylinositol 3-kinase inhibitors. 3-Hydroxyphenol analogues and bioisosteric replacements

Two classes of trisubstituted pyrimidines related to PI-103 1 have been prepared and their inhibitory activities against phosphatidylinositol 3-kinase (PI3K) p110α were determined. From those with direct 6-aryl substitution compound 11a was the most potent inhibitor with an IC50 value of 62 nM, and showed similar activity against other class 1a PI3K isoforms tested, p110β and p110γ. When a linking chain was introduced, as in the second exemplified class, compound 15f inhibited p110α with IC 50 142 nM, and showed greater selectivity towards p110α. Compounds of both classes showed promising inhibition of cellular proliferation in IGROV-1 ovarian cancer cells. Among compounds designed to replace the 3-phenolic motif with structural isosteres, analogues incorporating a 4-indazolyl group possessed enzyme and cellular activities comparable to the parent phenols.

Highly enantioselective synthesis of β-amino acid derivatives by the lewis base catalyzed hydrosilylation of β-enamino esters

A study was conducted to demonstrate highly enantioselective synthesis of β-amino acid derivatives by the Lewis base catalyzed hydrosilylation of βenamino esters. It was found that these catalyst and its analogue displayed excellent activities and enantioselectivities in promoting hydrosilylation of N-aryl β-enamino esters. N-picolinoylpyrrolidine derivatives and N-picolioylephedrine were also evaluated in hydrosilylation of (Z)-methyl 3-phenyl-3-(phenylamino)acrylate. The generality of the Lewis base organocatalyzed hydrosilylation of various β-enamino esters were examined under the optimized conditions. It was observed that the catalytic system exhibited a high sensitivity to the N-substituents, while all the N-aryl β-enamino esters underwent the hydrosilylation smoothly to give corresponding β-amino esters.

FUSED AZOLE-PYRIMIDINE DERIVATIVES

The present invention relates to hovel fused azolepyrimidine derivatives, processes for preparing them and pharmaceutical preparations containing them. The fused azolepyrimidine derivatives of the present invention exhibit enhanced potency for phosphotidy

Synthesis and muscarinic activities of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives

A series of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives (B) was synthesized and tested for muscarinic activity in receptor binding assays using [3H]-oxotremorine-M (3H-OXO-M) and [3H]-pirenzepine (3H-PZ) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies measuring their potencies to inhibit the binding of 3H-OXO-M and 3H-PZ. Preferential inhibition of 3H-OXO-M binding was used as an indicator for potential muscarinic agonistic properties; this potential was confirmed in functional studies on isolated organs. All compounds with agonistic properties showed 3H-PZ/3H-OXO-M potency ratios in excess of 20. In contrast, for antagonists this ratio was found to be close to unity. Mono-halogenation resulted in compounds (4b and 4d) with M3 agonistic properties as shown by their atropine sensitive stimulant properties in the guinea pig ileum, but with very little or no M1 activity. Some minor in vivo effects were observed for both these compounds, with the iodinated compound 4d inducing salivation. Compound 4d also showed some positive mnemonic properties in rats where spatial short-term memory had been compromised by temporary cholinergic depletion. These data indicate that some M3 agonism may be desired in therapeutic agents aimed at the treatment of the cognitive deficits of Alzheimer's disease patients.