cas 55613-22-4, ETHYL 6-OXO-2-PHENYL-1,6-DIHYDRO-5-PYRIMIDINECARBOXYLATE

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Design and synthesis of phenoxypyridyl acetamide or aryl-oxodihydropurine derivatives for the development of novel pet ligands targeting the translocator protein 18 kDa (TSPO)
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Lee, Jihye,Jung, Jae Ho,Lee, Byung Chul,Lee, Sang-Yoon
supporting information
p. 1874 - 1877
(2016/11/17)

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.).
Goto, Taiji,Shiina, Akiko,Yoshino, Toshiharu,Mizukami, Kiyoshi,Hirahara, Kazuki,Suzuki, Osamu,Sogawa, Yoshitaka,Takahashi, Tomoko,Mikkaichi, Tsuyoshi,Nakao, Naoki,Takahashi, Mizuki,Hasegawa, Masashi,Sasaki, Shigeki
p. 7025 - 7037
(2013/11/06)

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.
Lopes, Alexandra Basilio,Miguez, Eduardo,Kuemmerle, Arthur Eugen,Rumjanek, Victor Marcos,Fraga, Carlos Alberto Manssour,Barreiro, Eliezer J.
p. 11683 - 11704
(2013/11/06)

Desulfitative cross-coupling of protecting group-free 2-thiouracil derivatives with organostannanes
We here report a unique and efficient copper bromide mediated pallado-catalyzed coupling of protecting group-free 2-thiouracil derivatives with organostannanes. The nature of the copper appears to be crucial for successful cross coupling.
Sun, Qi,Suzenet, Franck,Guillaumet, Gerald
supporting information; experimental part
p. 3473 - 3476
(2010/08/06)

AMIDE COMPOUNDS AND USE OF THE SAME
A renin inhibitor comprising a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension and the like
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Page/Page column 79

(2012/02/06)

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
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Page/Page column 33

(2010/11/23)

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.
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Page/Page column 33

(2010/10/20)

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.
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(2008/06/13)

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.
Palanki, Moorthy S.S.,Erdman, Paul E.,Manning, Anthony M.,Ow, Arnold,Ransone, Lynn J.,Spooner, Cheryl,Suto, Carla,Suto, Mark
p. 1645 - 1648
(2007/10/03)

Tricyclic Heteroaromatic Systems Containing a Bridgehead Nitrogen Atom. Part 3. Triazolopyrazolopyrimidines, Tetrazolopyrazolopyrimidines and Pyrimidopyrazolotriazines
6-Phenyl-1H-pyrazolopyrimidin-3(2H)-one 16 has been prepared and converted into its 3-chloro 6, 3-thioxo 17 and 3-methylthio derivatives 9.Each of these could be converted into the 3-hydrazino derivative 3, cyclisation of which with carbon disulfide or triethyl orthoformate generated the fused 1,2,4-triazoles 23 and 20, respectively.Alternatively, the hydrazino derivative 3 gave a substituted hydrazide 26 or thiosemicarbazide 25, from which the 1,2,4-triazoles 21 and 22 respectively were obtained.The equilibrium between 3-azido-6-phenyl-1H-pyrazolopyrimidine 5 and 2-phenyl-9H-tetrazolopyrazolopyrimidine 27 was studied. 3-Diazo-4-methyl-6-phenyl-1H-pyrazolopyrimidine 29 was prepared by diazotisation of the corresponding amine 1 and converted into the 3-azido compound 4, which could not be cyclised to form a tetrazole.Finally, the diazo compound 29 readily formed the pyrimidopyrazolotriazine derivatives 32 and 33, when treated with pentane-2,4-dione and ethyl acetoacetate respectively.
Golec, Julian M. C.,Scrowston, Richard M.,Dunleavy, Michael
p. 239 - 244
(2007/10/02)

Antiallergy agents. I. 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylic acids and esters
The synthesis of some 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylic acids and esters with potent oral and intravenous antiallergic activity against passive cutaneous anaphylaxis in the rat is described. Requirements for high activity include a free NH group in the pyrimidinone nucleus and a small to medium size ortho alkoxy or alkenyloxy group on the phenyl ring. It is suggested that in the case of the highly active compounds hydrogen bonding occurs between a nitrogen of the pyrimidine ring and the ethereal oxygen. The nature of this bonding and its possible contribution to an optimum configuration for the molecules is discussed.
Juby,Hudyma,Brown,et al.
p. 263 - 269
(2007/10/08)

Bis(4-[4'-hydroxy-5'-carboxy-2'-pyrimidinyl]phenoxy)alkanes
5-Carboxypyrimidine derivatives and their pharmaceutically acceptable basic salts, and their use as antiallergy agents.
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(2008/06/13)