2415-85-2

Usage

Chemical Properties

Grey white flake crystalline powder

InChI:InChI=1/C11H13NO2/c1-8-3-5-10(6-4-8)12-11(14)7-9(2)13/h3-6H,7H2,1-2H3,(H,12,14)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 106-49-0 p-toluidine 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 103677-62-9 N-(1-p-tolylcarbamoyl-2-propylidene)benzamide oxime 
• 85322-34-5 (Z)-5-(p-methylphenylcarbamoyl)-methylene-3-phenyl-5,6-dihydro-4H-1,2,4-oxadiazine 
• 1694-31-1 tert-butyl acetoacetate 
• 31009-91-3 2-chloro-3-oxo-N-(ptolyl)butanamide 
• 5396-89-4 benzyl acetoacetate 
• 105-45-3 acetoacetic acid methyl ester 
• 542-08-5 isopropyl acetoacetate 
• 1118-84-9 allyl acetoacetate 

Downstream Products

• 115080-99-4 2-xanthen-9-yl-acetoacetic acid p-toluidide 
• 23947-37-7 2-hydroxy-6-methyllepidine 
• 34797-70-1 acetoacetic acid-(4-methyl-2-nitro-anilide) 
• 103677-64-1 N-(p-Tolyl)-3-hydroxybutanamide 
• 55213-71-3 2-iodo-acetoacetic acid p-toluidide 
• 31009-91-3 2-chloro-3-oxo-N-(ptolyl)butanamide 
• 51903-75-4 Acetoacet-p-toluidid-2,3-dioxim 
• 13663-91-7 2-Anilinothiocarbonyl-acetessigsaeure-(4-methyl-anilid) 
• 94711-62-3 (2-Hydroxy-5-sulfamoyl-phenylazo)-4-methyl-acetoacetanilid 
• 112697-64-0 2-Methyl-[1,8]naphthyridine-3-carboxylic acid p-tolylamide 
• 139050-57-0 4-(4-methylphenylcarbamoyl)-3-methyl-6,6-diphenyl-1,2-dioxan-3-ol 
• 130087-96-6 (3-Methyl-5-p-tolylamino-pyrazol-1-yl)-pyridin-4-yl-methanone 
• 138201-43-1 N'-[1-Methyl-2-p-tolylcarbamoyl-eth-(E)-ylidene]-phosphorohydrazidic acid diphenyl ester 
• 139050-81-0 6,6-bis(4-methylphenyl)-4-(4-methylphenylcarbamoyl)-3-methyl-1,2-dioxan-3-ol 

Relevant academic research and scientific papers

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives

Abstract: A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.

Synthesis and anticonvulsant activity of some 1,4-dihydropyridine derivatives

A series of asymmetrical 4-alkyl/aryl-2,6-dimethyl-3-N-(aryl/heteroaryl)-carbamoyl-5-ethoxycarbonyl-1, 4-dihydropyridines 3a-d and symmetrical 4-alkyl/aryl-2,6-dimethyl-3,5-bis-(ethoxycarbonyl)-1,4-dihydropyridines 4a and 4b have been prepared by the condensation of various benzaldehydes, ethylacetoacetate, 2-aminopyridine or p-toludine in ethanol (Hantzch method). The structures of all the synthesized 1,4-dihydropyridine derivatives have been confirmed by spectral data (IR,1H NMR) and elemental analysis. Compounds 3a-c, 4a and 4b (10 mg/kg) have been evaluated for their anticonvulsant effect against pentylenetetrazole- induced convulsions with phenytoin (4 mg/kg) as the standard. The anticonvulsant potential of the newly synthesized compounds have been assessed on the basis of increase in latency (onset time) to induce convulsions; decrease in number of convulsions and increase in latency of death compared to control and standard.

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst

A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.

Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators

Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 μM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 μM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

2- Amino -3,4-dihydropyran -3- formamide analogue as well as preparation method and application thereof

The invention relates to a preparation method 2 - of a compound containing, amino - 333384-dihydropyran - 3 3, which comprises the following step :1) of linking diketene with R. 2 NH2 The reaction is stirred in a solvent to complete. ;2) Is added R. 3 NH2 , R1 CHO And a of Compound, and adding elemental iodine to reaction solution to complete curing, and drying the filter cake to obtain compound 2 - containing. amino - 3333,4-dihydropyran - 3 3-carboxamide compound, according to the present invention as well as its use. without isolation of intermediate, in a simple.

5-Aminothiophene-2,4-dicarboxamide analogues as hepatitis B virus capsid assembly effectors

Chronic hepatitis B virus (HBV) infection represents a major health threat. Current FDA-approved drugs do not cure HBV. Targeting HBV core protein (Cp) provides an attractive approach toward HBV inhibition and possibly infection cure. We have previously identified and characterized a 5-amino-3-methylthiophene-2,4-dicarboxamide (ATDC) compound as a structurally novel hit for capsid assembly effectors (CAEs). We report herein hit validation through studies on absorption, distribution, metabolism and excretion (ADME) properties and pharmacokinetics (PK), and hit optimization via analogue synthesis aiming to probe the structure-activity relationship (SAR) and structure-property relationship (SPR). In the end, these medicinal chemistry efforts led to the identification of multiple analogues strongly binding to Cp, potently inhibiting HBV replication in nanomolar range without cytotoxicity, and exhibiting good oral bioavailability (F). Two of our analogues, 19o (EC50 = 0.11 μM, CC50 > 100 μM, F = 25%) and 19k (EC50 = 0.31 μM, CC50 > 100 μM, F = 46%), displayed overall lead profiles superior to reported CAEs 7–10 used in our studies.

Synthesis of β-Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities

Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in?vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

Compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds

The invention provides 7-substituted-5-methyl-1,2,4-triazolo[4,3-a] quinoline and 7-substituted-5-ethoxy-[1,2,4]-triazolo[4,3-a] quinoline compounds having anticonvulsion activity, preparing methods thereof and applications of the compounds in the field of preparing anticonvulsion medicines.