3435-29-8

Usage

Uses

6-PHENYLPYRIMIDIN-4-AMINE is a useful research chemical.

InChI:InChI=1/C10H9N3/c11-10-6-9(12-7-13-10)8-4-2-1-3-5-8/h1-7H,(H2,11,12,13)

Upstream product

• 1823-99-0 3-amino-3-phenylacrylonitrile 
• 77287-34-4 formamide 
• 143407-66-3 2-(thiazolin-2-yl)-1-phenyl-1-ethenamine 
• 122-51-0 orthoformic acid triethyl ester 
• 5305-59-9 4-amino-6-chloropyrimidine 
• 98-80-6 phenylboronic acid 
• 3438-48-0 4-phenylpyrimidine 

Downstream Products

• 4891-69-4 4-phenyl-6(1H)-pyrimidinone 
• 111677-67-9 6-Amino-4-phenylpyrimidine 1-Oxide 
• 1192807-65-0 (R)-N-(6-phenylpyrimidin-4-yl)-4H-1'-azaspiro[oxazole-5,3'-bicyclo[2.2.2]octan]-2-amine 
• 1313547-56-6 4-nitro-N-(6-phenylpyrimidin-4-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Discovery of coumarin derivatives as potent and selective cyclin-dependent kinase 9 (CDK9) inhibitors with high antitumour activity

Specific inhibition of CDK9 is considered a promising strategy for developing effective anticancer therapeutics. However, most of the reported CDK9 inhibitors are still at an early stage of development and lack selectivity against other CDKs. Herein, we discovered coumarin derivative 30i as a potent CDK9 inhibitor with high selectivity (8300-fold over CDK7). Binding mode analysis illustrated that the substituent coumarin moiety is a critical group for CDK9 selectivity by occupying a flexible hinge/αD region, which is sterically hindered in other CDKs. Compound 30i showed excellent cellular antiproliferative activity, moderate pharmacokinetic property and low hERG inhibition. Moreover, 30i significantly induced tumour growth inhibition in a dose-dependent manner without causing an obvious loss of body weight in an MV4-11 xenograft mice model. Altogether, these results suggest that 30i may serve as a potential acute myeloid leukaemia (AML) therapeutics by selectively targeting CDK9.

BMS-933043, a Selective α7 nAChR Partial Agonist for the Treatment of Cognitive Deficits Associated with Schizophrenia

The therapeutic treatment of negative symptoms and cognitive dysfunction associated with schizophrenia is a significant unmet medical need. Preclinical literature indicates that α7 neuronal nicotinic acetylcholine (nACh) receptor agonists may provide an effective approach to treating cognitive dysfunction in schizophrenia. We report herein the discovery and evaluation of 1c (BMS-933043), a novel and potent α7 nACh receptor partial agonist with high selectivity against other nicotinic acetylcholine receptor subtypes (>100-fold) and the 5-HT3A receptor (>300-fold). In vivo activity was demonstrated in a preclinical model of cognitive impairment, mouse novel object recognition. BMS-933043 has completed Phase I clinical trials.

Design and synthesis of a novel series of 4-heteroarylamino-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octanes as α7 nicotinic receptor agonists 2. Development of 4-heteroaryl SAR

Quinuclidine-containing spirooxazolines, as described in the previous report in this series, were demonstrated to have utility as α7 nicotinic acetylcholine receptor (α7 nAChR) partial agonists. In this work, the SAR of this chemotype was expanded to include an array of diazine heterocyclic substitutions. Many of the heterocyclic analogs were potent partial agonists of the α7 receptor, selective against other nicotinic receptors and the serotinergic 5HT3A receptor. (1′S,3′R,4′S)-N-(6-phenylpyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine, a potent and selective α7 nAChR partial agonist, was demonstrated to improve cognition in the mouse novel object recognition (NOR) model of episodic memory.

Α 7 as intranuclear hydroxynicotinic acetylcholine receptor quinuclidines compd.

PROBLEM TO BE SOLVED: To provide ligands for the nicotinic α-7 receptor used for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.SOLUTION: The disclosure provides compounds of the specified formula I, including their salts, and compositions and methods using the compounds.

QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS

The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the nicotinic 7 receptor and may be useful for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.

An unprecedented approach to 4,5-disubstituted pyrimidine derivatives by a ZnCl2-catalyzed three-component coupling reaction

We have developed a ZnCI2-catalyzed three-component coupling reaction involving a variety of functionalized enamines, triethyl orthoformate, and ammonium acetate, which leads to the production of 4,5-disubstituted pyrimidine derivatives in a single step. The procedure can be successfully applied to the efficient synthesis of mono- and disubstituted pyrimidine derivatives, using methyl ketone derivatives instead of enamines.

QUINUCLIDINE COMPOUNDS AS ALPHA-7 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS

The disclosure provides compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds are ligands for the nicotinic α7 receptor and may be useful for the treatment of various disorders of the central nervous system, especially affective and neurodegenerative disorders.

The Chichibabin amination of 4-phenyl- and 4-tert-butyl-pyrimidine

During a study on the amination of 4-phenylpyrimidine in potassium amide/liquid ammonia it was found that the extent to which the SN(ANRORC) mechanism operates in the amination largely depends upon whether an ammonium salt is used in quenching the reaction.The composition of the ?-adduct mixture, the structure of the open-chain intermediates, the inhibition of the SN(ANRORC) mechanism and the course of the amination in apolar solvents have been investigated.In addition, it has been found that, in the amination of 4-tert-butylpyrimidine, the SN(ANRORC) mechanism occurs to only a very limited extent.