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Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is used as a building block for the synthesis of various pharmaceutical products due to its potential biological activity and wide range of applications in medicinal chemistry.
Used in Antiviral Applications:
In the pharmaceutical industry, ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is used as a key component in the development of antiviral drugs, contributing to the creation of medications that combat viral infections.
Used in Antifungal Applications:
ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is utilized as a component in the development of antifungal drugs, playing a role in creating medications that treat fungal infections.
Used in Anticancer Applications:
This chemical compound is used in the development of anticancer drugs, where it may contribute to the creation of medications that target and treat cancer cells.
Used in Pesticide Industry:
ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is studied for its potential as an insecticide and herbicide, due to its structural properties that may offer pesticidal effects in controlling pests and unwanted plant growth.
Used as an Intermediate in Organic Synthesis:
In the field of organic chemistry, ETHYL 4-CHLORO-2-PHENYL-5-PYRIMIDINECARBOXYLATE is used as an intermediate in the synthesis of other organic compounds, facilitating the creation of a variety of chemical products.

InChI:InChI=1/C13H11ClN2O2/c1-2-18-13(17)10-8-15-12(16-11(10)14)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 55613-22-4 4-hydroxy-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester 
• 618-39-3 benzamidin 
• 55613-22-4 ethyl 4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carboxylic acid 
• 1670-14-0 benzamidine monohydrochloride 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 34750-39-5 9-(2-dimethylamino-ethyl)-2-phenyl-8,9-dihydro-7H-pyrimido[4,5-e][1,4]oxazepin-5-one 
• 34750-41-9 9-(2-ethoxy-ethyl)-2-phenyl-8,9-dihydro-7H-pyrimido[4,5-e][1,4]oxazepin-5-one 
• 34750-43-1 2-phenyl-9-(3-piperidin-1-yl-propyl)-8,9-dihydro-7H-pyrimido[4,5-e][1,4]oxazepin-5-one 
• 32656-93-2 9-(2-hydroxy-propyl)-7-methyl-2-phenyl-8,9-dihydro-7H-pyrimido[4,5-e][1,4]oxazepin-5-one 
• 97693-08-8 2-phenyl-5H-pyrido<1,2-a>pyrimido<5,4-e>pyrimidin-5-one 
• 97693-09-9 2-phenyl-4-(2-pyridylamino)-5-pyrimidinecarboxylic acid ethyl ester 
• 78494-30-1 4-tert-Butylperoxy-2-phenyl-pyrimidine-5-carboxylic acid ethyl ester 
• 135370-76-2 5-ethoxycarbonyl-4-(1,1-dimethylpropylperoxy)-2-phenylpyrimidin 
• 135370-77-3 5-ethoxycarbonyl-4-(1,1-diethylpropylperoxy)-2-phenylpyrimidin 
• 135370-78-4 5-ethoxycarbonyl-4-(1,1-dimethylpropargylperoxy)-2-phenylpyrimidin 
• 135370-91-1 5-ethoxycarbonyl-4-(1,1-dimethyl-4-phenylbutylperoxy)-2-phenylpyrimidin 
• 135370-87-5 5-ethoxycarbonyl-4-<1,1-dimethyl-3-(4-methylphenyl)-propylperoxy>-2-phenylpyrimidin 
• 135370-86-4 5-ethoxycarbonyl-4-<1,1-dimethyl-3-(2-methylphenyl)-propylperoxy>-2-phenylpyrimidin 
• 135370-85-3 5-ethoxycarbonyl-4-(1,1-dimethyl-3-phenyl-propylperoxy)-2-phenylpyrimidin 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 5-carbamoyl-2-phenylpyrimidine derivatives as novel and potent PDE4 inhibitors

5-Carbamoyl-2-phenylpyrimidine derivative 2 has been identified as a phosphodiesterase 4 (PDE4) inhibitor with moderate PDE4B inhibitory activity (IC50 = 200 nM). Modification of the carboxylic acid moiety of 2 gave N-neopentylacetamide derivative 10f, which had high in vitro PDE4B inhibitory activity (IC50 = 8.3 nM) and in vivo efficacy against lipopolysaccharide (LPS)-induced pulmonary neutrophilia in mice (ID50 = 16 mg/kg, ip). Furthermore, based on the X-ray crystallography of 10f bound to the human PDE4B catalytic domain, we designed 7,8-dihydro-6H-pyrido[4,3-d] pyrimidin-5-one derivative 39 which has a fused bicyclic lactam scaffold. Compound 39 exhibited excellent inhibitory activity against LPS-induced tumor necrosis factor alpha (TNF-α) production in mouse splenocytes (IC 50 = 0.21 nM) and in vivo anti-inflammatory activity against LPS-induced pulmonary neutrophilia in mice (41% inhibition at a dose of 1.0 mg/kg, i.t.).

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.

SUBSTITUTED HETEROCYCLIC COMPOUNDS AND METHODS OF USE

The present invention relates to pyridines, pyrimidines and derivatives thereof, and pharmaceutically acceptable salts thereof. Also included is a method of treatment of inflammation, rheumatoid arthritis, Pagets disease, osteoporosis, multiple myeloma, uveititis, acute or chronic myelogenous leukemia, pancreatic beta cell destruction, osteoarthritis, rheumatoid spondylitis, gouty arthritis, inflammatory bowel disease, adult respiratory distress syndrome (ARDS), psoriasis, Crohn's disease, allergic rhinitis, ulcerative colitis, anaphylaxis, contact dermatitis, asthma, muscle degeneration, cachexia, Reiter's syndrome, type I diabetes, type II diabetes, bone resorption diseases, graft vs. host reaction, Alzheimer's disease, stroke, myocardial infarction, ischemia reperfusion injury, atherosclerosis, brain trauma, multiple sclerosis, cerebral malaria, sepsis, septic shock, toxic shock syndrome, fever, myalgias due to HIV-1, HIV-2, HIV-3, cytomegalovirus (CMV), influenza, adenovirus, the herpes viruses or herpes zoster infection in a mammal comprising administering an effective amount a compound as described above.

PYRIMIDINE CARBOXYLIC ACID DERIVATIVES AND USE THEREOF

The invention relates to pyrimidine carboxylic acid derivatives of formula (I), to methods for the production thereof, to their use for treating and/or preventing diseases, and their use for producing medicaments for treating and/or preventing diseases, p

2-aryl-8-oxodihydropurine derivative, process for the producing the same, medicinal compositions containing the same, and intermediates thereof

2-Aryl-8-oxodihydropurine derivative of the following formula (I): wherein W is H, lower alkyl, halogen, lower alkoxy, amino, mono- or di-lower alkylamino, or substituted or unsubstituted phenyl; X is H, lower alkyl, cycloalkyl-lower alkyl, substituted or unsubstituted phenyl-lower alkyl, lower alkenyl, carbamoyl, di-lower alkylcarbamoyl, or a group of the formula (Q): —CH(R3)CON(R1)(R2); Y is H, lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, lower alkenyl, substituted or unsubstituted phenyl-lower alkyl, or a group of the formula (Q): —CH(R3)CON(R1)(R2); A is substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl; provided that when one of X and Y of the above formula (I) is the group of the formula (Q), then the other is the same groups for X or Y as described above except for the group of the formula (Q), or a pharmaceutically acceptable acid addition salt thereof. These compounds are useful for the prophylaxis or treatment of central nervous disorders such as anxiety-related diseases (neurosis, somatoform disorders, anxiety disorders, and others), depression, epilepsy, etc., or circulatory organs disorders such as angina pectoris, hypertension.

Novel inhibitors of AP-1 and NF-κB mediated gene expression: Structure-activity relationship studies of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate

In an effort to identify novel inhibitors of AP-1 and NF-κB mediated transcriptional activation, several analogues of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate (1) were synthesized and tested in two in vitro assays. The 2-(2'-thienyl) substituted compound (11) was identified as the most potent in this series. (C) 2000 Elsevier Science Ltd. All rights reserved.