5470-24-6

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General Description

6-Chloro-9-phenyl-9H-purine is a chemical compound with the molecular formula C11H7ClN4. It is a derivative of purine, a heterocyclic organic compound. 6-Chloro-9-phenyl-9H-purine has a chloro group at the 6th position and a phenyl group at the 9th position of the purine ring. It has potential applications in the pharmaceutical industry, particularly in the development of new drugs. Its structure and properties make it suitable for further chemical modifications to create novel compounds with potential therapeutic properties. Research on 6-Chloro-9-phenyl-9H-purine and its analogs may lead to the development of new medications for various medical conditions.

InChI:InChI=1/C14H16N2O3/c1-9-10(16-17)8-11(12-4-2-6-18-12)15-14(9)13-5-3-7-19-13/h2-7,9,11,14-15,17H,8H2,1H3/b16-10-

Upstream product

• 6334-42-5 1,9-dihydro-9-phenyl-6H-purin-6-one 
• 87-42-3 6-chloropurine 
• 98-80-6 phenylboronic acid 
• 64995-55-7 1-phenyl-5-aminoimidazole-4-carboxamide 
• 62-53-3 aniline 
• 1483-72-3 diphenyliodonium chloride 
• 41259-65-8 6-chloro-N₄-phenylpyrimidine-4,5-diamine 
• 3724-43-4 Vilsmeier reagent 
• 885619-01-2 ethyl 5-amino-1-phenyl-1H-imidazole-4-carboxylate 

Downstream Products

• 108990-53-0 dimethyl-(9-phenyl-9H-purin-6-yl)-amine 
• 21314-09-0 1,9-dihydro-9-phenyl-6H-purine-6-thione 
• 122625-37-0 methyl-(9-phenyl-9H-purin-6-yl)-amine 
• 135426-10-7 N⁶-(1-phenyl-2(S)-propyl)-9-phenyladenine 
• 135394-15-9 N⁶-(1-phenyl-2(R)-propyl)-9-phenyladenine 
• 62196-39-8 9-phenyl-9H-purine-6-carbonitrile 
• 119980-67-5 9-phenyl-6-phenylethynyl-9H-purine 
• 70386-27-5 N-phenyl-N-(9-phenyl-9H-purin-6-yl)amine 
• 119980-68-6 6-(1-hexynyl)-9-phenyl-9H-purine 
• 135394-13-7 Cyclopentyl-(9-phenyl-9H-purin-6-yl)-amine 
• 119980-70-0 9-phenyl-6-<2-(trimethylsilyl)ethynyl>-9H-purine 
• 20145-09-9 SQ 22517 
• 119980-74-4 6-iodo-9-phenyl-9H-purine 
• 85107-09-1 phenyl(9-phenyl-9H-purin-6-yl)methanone 

Relevant academic research and scientific papers

METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES

The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functi

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

GLUCOSE TRANSPORT INHIBITORS

The present invention relates to chemical compounds of general formula (I): in which RA, RB, RC, RD, m, and n are as given in the description and in the claims, and which effectively and selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, as well as to intermediate compounds useful in the preparation of said compounds.

CuBr catalyzed C-N cross coupling reaction of purines and diaryliodonium salts to 9-arylpurines

CuBr was found to be an efficient catalyst for the C-N cross coupling reaction of purine and diaryliodonium salts. 9-Arylpurines were synthesized in excellent yields with short reaction times (2.5 h). The method represents an alternative to the synthesis of 9-arylpurines via Cu(ii) catalyzed C-N coupling reaction with arylboronic acids as arylating agents. The Royal Society of Chemistry 2011.

Enhanced selectivity for inhibition of analog-sensitive protein kinases through scaffold optimization

The ability to inhibit any protein kinase of interest with a small molecule is enabled by a combination of genetics and chemistry. Genetics is used to modify the active site of a single kinase to render it distinct from all naturally occurring kinases. Next, organic synthesis is used to develop a small molecule, which does not bind to wild-type kinases but is a potent inhibitor of the engineered kinase. This approach, termed chemical genetics, has been used to generate highly potent mutant kinase-specific inhibitors based on a pyrazolopyrimidine scaffold. Here, we asked if the selectivity of the resulting pyrazolopyrimidines could be improved, as they inhibit several wild-type kinases with low-micromolar IC50 values. Our approach to improve the selectivity of allele-specific inhibitors was to explore a second kinase inhibitor scaffold. A series of 6,9-disubstituted purines was designed, synthesized, and evaluated for inhibitory activity against several kinases in vitro and in vivo. Several purines proved to be potent inhibitors against the analog-sensitive kinases and exhibited greater selectivity than the existing pyrazolopyrimidines.

Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II)

9-Arylpurines are efficiently formed with complete regioselectivity when purines are treated with arylboronic acids in the presence of copper(II) acetate. A variety of substituents on both coupling partners are well tolerated.

ETHYL CHLOROFORMATE/DMF IN ORGANIC SYNTHESIS. I. A NOVEL REAGENT FOR RING CLOSURE OF 5-AMINO-1-ARYL-4-IMIDAZOLECARBOXAMIDES TO THEIR HYPOXANTHINE DERIVATIVES

Ethyl chloroformate/dimethylformamide mixture is used as a new reagent for adding a carbon (C-2 in the purine nucleus) at the formic acid oxidation level during ring closure of 5-amino-1-aryl-4-imidazolecarboxamides leading to the formation of the corresp