85386-14-7

Usage

Uses

Used in Pharmaceutical Research and Development:
Ethyl 2-phenylpyrimidine-5-carboxylate is utilized as a precursor or intermediate in the synthesis of pharmaceutical drugs. Its pyrimidine backbone provides a versatile chemical structure that can be modified to create a range of active pharmaceutical ingredients, contributing to the development of new medications with specific therapeutic properties.
Used in Drug Synthesis:
In the pharmaceutical industry, ethyl 2-phenylpyrimidine-5-carboxylate is employed as a key component in the synthesis of various drugs. Its unique chemical structure allows for the creation of compounds with targeted therapeutic effects, making it a valuable asset in the development of new treatments for a range of medical conditions.
Used in Medicinal Chemistry:
Ethyl 2-phenylpyrimidine-5-carboxylate is also used in medicinal chemistry for the design and optimization of drug candidates. Its pyrimidine backbone can be modified to explore different chemical entities with potential therapeutic benefits, facilitating the discovery of novel drugs with improved efficacy and safety profiles.

InChI:InChI=1/C13H12N2O2/c1-2-17-13(16)11-8-14-12(15-9-11)10-6-4-3-5-7-10/h3-9H,2H2,1H3

Upstream product

• 97430-37-0 2-(ethoxycarbonyl)-3-hydroxyacrolein 
• 618-39-3 benzamidin 
• 623-47-2 propynoic acid ethyl ester 
• 80370-42-9 ethyl 2-formyl-3-oxopropanoate 
• 1670-14-0 benzamidine monohydrochloride 
• 89793-12-4 ethyl 2-chloropyrimidine-5-carboxylate 
• 98-80-6 phenylboronic acid 
• 122774-00-9 2-phenylpyrimidine-5-carbonyl chloride 
• 122773-97-1 2-phenylpyrimidine-5-carboxylic acid 
• 92385-43-8 ethyl 3-(dimethylamino)-2-formylprop-2-enoate 
• 24755-82-6 ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate 
• 122773-94-8 5-amidino-2-phenylpyrimidine hydrochloride 
• 64-17-5 ethanol 
• 85386-15-8 2-phenylpyrimidine-5-carbonitrile 

Downstream Products

• 1604047-92-8 2-phenylpyrimidine-5-carbohydrazide 
• 1604047-95-1 N′-(4-(dimethylamino)benzylidene)-2-phenylpyrimidine-5-carbohydrazide 
• 7431-45-0 2-phenylpyrimidine 
• 122774-00-9 2-phenylpyrimidine-5-carbonyl chloride 
• 122773-97-1 2-phenylpyrimidine-5-carboxylic acid 

Relevant academic research and scientific papers

cGAS ANTAGONIST COMPOUNDS

Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents

To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for improving the activity against Aspergillus spp. Among these compounds, 2-F substituted analogues 23g and 23h displayed the most remarkable in vitro activity against Candida spp., C. neoformans, A. fumigatus and fluconazole-resistant C.alb. strains, which is superior or comparable to the activity of the reference drugs fluconazole and voriconazole. Notably, the compounds 23g and 23h exhibited low inhibition profiles for various isoforms of human cytochrome P450 and excellent blood plasma stability.

Characterization of amide bond conformers for a novel heterocyclic template of N-acylhydrazone derivatives

Herein we describe NMR experiments and structural modifications of 4-methyl-2-phenylpyrimidine-N-acylhydrazone compounds (aryl-NAH) in order to discover if duplication of some signals in their 1H- and 13C-NMR spectra was related to a mixture of imine double bond stereoisomers (E/Z) or CO-NH bond conformers (syn and anti-periplanar). NMR data from NOEdiff, 2D-NOESY and 1H-NMR spectra at different temperatures, and also the synthesis of isopropylidene hydrazone revealed the nature of duplicated signals of a 4-methyl-2-phenylpyrimidine-N-acylhydrazone derivative as a mixture of two conformers in solution. Further we investigated the stereoelectronic influence of substituents at the ortho position on the pyrimidine ring with respect to the carbonyl group, as well as the electronic effects of pyrimidine by changing it to phenyl. The conformer equilibrium was attributed to the decoplanarization of the aromatic ring and carbonyl group (generated by an ortho-alkyl group) and/or the electron withdrawing character of the pyrimidine ring. Both effects increased the rotational barrier of the C-N amide bond, as verified by the ΔG≠ values calculated from dynamic NMR. As far as we know, it is the first description of aryl-NAH compounds presenting two CO-NH bond-related conformations.

Inhibitors of NF-kappaB and AP-1 gene expression: SAR studies on the pyrimidine portion of 2-chloro-4-trifluoromethylpyrimidine-5-[N-(3', 5'-bis(trifluoromethyl)phenyl)carboxamide].

We investigated the structure-activity relationship studies of N-[3, 5-bis(trifluoromethyl)phenyl][2-chloro-4-(trifluoromethyl)pyrimidin-5 -yl]carboxamide (1), an inhibitor of transcription mediated by both NF-kappaB and AP-1 transcription factors, with the goal of improving its potential oral bioavailability. Compounds were examined for cell-based activity, were fit to Lipinski's rule of 5, and were examined for potential gastrointestinal permeability using the intestinal epithelial cell line, Caco-2. Selected groups were substituted at the 2-, 4-, and 5-positions of the pyrimidine ring using solution-phase combinatorial methodology. The introduction of a fluorine in the place of 2-chlorine of 1 resulted in a compound with comparable activity. However, other substitutions at the 2-position resulted in a loss of activity. The trifluoromethyl group at the 4-position could be replaced with a methyl, ethyl, chlorine, or phenyl without a substantial loss of activity. The carboxamide group at the 5-position is critical for activity. If it was moved to the 6-position, the activity was lost. The 2-methyl analogue of 1 (81) showed comparable in vitro activity and improved Caco-2 permeability compared to 1.

Pyrimidine carboxamides and related compounds and methods for treating inflammatory conditions

Compounds having utility as antinflammatory agents in general and, more specifically, for the prevention and/or treatment of immunoinflammatory and autoimmune diseases are disclosed. The compounds are pyrimidine- or pyrazine-containing compounds and, in one embodiment, are carboxyamides of the same. Methods are also disclosed for preventing and/or treating inflammatory conditions by administering to an animal in need thereof an effective amount of a compound of this invention, preferably in the form of a pharmaceutical composition.

1,3-Diaza-1,3-butadienes. Synthesis and conversion into pyrimidines by [4π + 2π] cycloaddition with electron deficient acetylenes. Synthetic utility of 2-(trichloromethyl)pyrimidines

Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4π ± 2π] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on heating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 26. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the 1H-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by 1H NMR spectroscopy, and which aromatize to pyrimidines 20 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes. These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

SYNTHESIS OF ISOMERIC AMINOPHENYLBIPYRIMIDINES AND STUDY OF THE LIQUID CRYSTALLINE PROPERTIES OF ANILS STRUCTURALLY RELATED TO AMINOPHENYLPYRIMIDINES

5-amino-2,5'-bipyrimidines and bis-(5-aminopyrimidinyl-2)-p-phenylenes have been synthesized as well as isomeric bis-(p-aminophenyl)pyrimidines.From these, substituted benzylidenamino derivatives have been prepared and their liquid crystalline properties studied.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. VIII. Synthesis of Ethyl and Methyl 2,4-Disubstituted 5-Pyrimidinecarboxylates

Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with N-C-N dinucleophiles such as guanidine, acetamidine or benzamidine afforded in high yields the relative esters of 4-substituted 2-amino-, 2-methyl- or 2-phenyl-5-pyrimidinecarboxylic acids, respectively.These esters were hydrolyzed to the corresponding carboxylic acids, which were converted by heating to 4-substituted 2-pyrimidinamines, 2-methyl or 2-phenylpyrimidines, respectively, generally in excellent yields.The 4-unsubstituted ethyl 2-amino-, 2-methyl- and 2-phenyl-5-pyrimidinecarboxylateswere obtained in moderate yields by reaction of the above dinucleophiles with ethyl 2,2-diformylacetate.These esters were hydrolyzed and the corresponding acids (with the exception of the 2-methyl derivative) were decarboxylated to give 2-pyrimidinamine and 2-phenylpyrimidine in satisfactory yields.

SYNTHESIS OF 2,5'-BIPYRIMIDINES FROM SUBSTITUTED 5-CYANOPYRIMIDINES

The Pinner method was applied to substituted 5-cyanopyrimidines to obtain 5-aminopyrimidines, which were condensed with acrolein derivatives to synthesize compounds that contain a 2,5-bipyrimidine fragment.