352303-65-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,6-DIFLUORO-BENZYL)-6-METHYL-1H-PYRIMIDINE-2,4-DIONE is used as a chemical intermediate for the development of pharmaceutical drugs. Its unique structural features, including the presence of a benzyl group with two fluorine atoms and a methyl substituent, make it a promising candidate for the creation of new medications with potential therapeutic benefits.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1-(2,6-DIFLUORO-BENZYL)-6-METHYL-1H-PYRIMIDINE-2,4-DIONE serves as a valuable compound for research and development. Its structural properties allow scientists to explore its potential interactions with biological targets, which could lead to the discovery of new drugs with improved efficacy and safety profiles.

InChI:InChI=1/C12H10F2N2O2/c1-7-5-11(17)15-12(18)16(7)6-8-9(13)3-2-4-10(8)14/h2-5H,6H2,1H3,(H,15,17,18)

Upstream product

• 618914-13-9 1-(2,6-difluorobenzyl)-3-(3-oxobutyryl)urea 
• 674-82-8 4-methyleneoxetan-2-one 
• 17751-24-5 N-(2,6-difluorobenzyl) urea 
• 69385-30-4 2,6-difluorobenzylamine 

Downstream Products

• 352292-05-8 1-(2,6-difluoro-benzyl)-3-[2-(3-isobutoxy-propylamino)-propyl]-5-(3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 352291-93-1 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-[2-(2-pyridin-2-yl-ethylamino)-propyl]-1H-pyrimidine-2,4-dione 
• 352293-98-2 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-{2-[(pyridin-2-ylmethyl)-amino]-propyl}-1H-pyrimidine-2,4-dione 
• 352291-90-8 3-(2-benzylamino-propyl)-1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 352292-25-2 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-pyrrolidin-2-ylmethyl-1H-pyrimidine-2,4-dione 
• 618914-15-1 1-(2,6-difluoro-benzyl)-5-(3-methoxy-phenyl)-6-methyl-3-(2-oxo-propyl)-1H-pyrimidine-2,4-dione 
• 618914-14-0 5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-3-(2-methyl-allyl)-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

5-Aryluracils as potent GnRH antagonists-Characterization of atropisomers

Optimization of a series of uracils bearing a 2-fluoro- or 2-chloro-3-methoxyphenyl group at the 5-position resulted in compounds such as 3d and 3f with subnanomolar binding affinity at the human GnRH receptor. While the 2-fluoro-3-methoxyphenyl compound 3a was characterized as a mixture of interchangeable atropisomers, the diastereoisomers of 2-chloro-3-methoxyphenyl analogs were separated. It was found that the aR-atropisomer was much more potent than the aS-isomer based on the X-ray crystal structure of 3h-II.

Discovery of sodium R-(+)-4-{2-[5-(2-Fluoro-3-methoxyphenyl)-3-(2-fluoro-6- [trifluoromethyl]-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl] -1-phenylethylamino}butyrate (elagolix), a potent and orally available nonpeptide antagonist of the human gonadotropin-releasing hormone receptor

The discovery of novel uracil phenylethylamines bearing a butyric acid as potent human gonadotropin-releasing hormone receptor (hGnRH-R) antagonists is described. A major focus of this optimization was to improve the CYP3A4 inhibition liability of these uracils while maintaining their GnRH-R potency. R-4-{2-[5-(2-Fluoro-3-methoxyphenyl)-3-(2-fluoro-6-[trifluoromethyl]benzyl) -4-methyl-2,6-dioxo-3,6-dihy-dro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyric acid sodium salt, 10b (elagolix), was identified as a potent and selective hGnRH-R antagonist. Oral administration of 10b suppressed luteinizing hormone in castrated macaques. These efforts led to the identification of 10b as a clinical compound for the treatment of endometriosis.

Synthesis and Structure-Activity Relationships of 1-Arylmethyl-5-aryl-6-methyluracils as Potent Gonadotropin-Releasing Hormone Receptor Antagonists

Based on the SAR from bicyclic gonadotropin-releasing hormone (GnRH) antagonists such as 6-aminomethyl-7-aryl-pyrrolo [1,2-a] pyrimid-4-ones (5) and 2-aryl-3-aminomethyl-imidazolo-[1,2-a]pyrimid-5-ones (6a,b), a series of novel uracil compounds (8) were d

Synthesis and structure-activity relationships of uracil derived human GnRH receptor antagonists: (R)-3-[2-(2-amino)phenethyl]-1-(2,6-difluorobenzyl)-6- methyluracils containing a substituted thiophene or thiazole at C-5

The design and synthesis of a number of 5-thiazolyl and 5-thienyl substituted uracils is described and results from SAR studies are summarized. The best compound showed Ki = 2 nM. The synthesis of a series of (R)-3-[2-(2-amino)phenethyl]-1-(2,6

Synthesis and structure-activity relationships of 1-arylmethyl-3-(2-aminopropyl)-5-aryl-6-methyluracils as potent GnRH receptor antagonists

The novel synthesis and SAR studies of 6-methyluracils as human GnRH receptor antagonists are discussed. Introduction of a small methyl substituent at the β-position from N3 of the uracil improved the GnRH binding potency by 5- to 10-fold. The best compou

Gonadotropin-releasing hormone receptor antagonists and methods relating thereto

GnRH receptor antagonists are disclosed which have utility in the treatment of a variety of sex-hormone related conditions in both men and women. The compounds of this invention have the structure: wherein A, Q, R1, R2, R3a, R3b, R4, R5, R6 and n are as defined herein, including stereoisomers, prodrugs and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound of this invention in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for antagonizing gonadotropin-releasing hormone in a subject in need thereof.