4835-39-6

Usage

Chemical Properties

Bright yellow crystalline powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 2431, 1985 DOI: 10.1021/jo00214a006

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 100-01-6 4-nitro-aniline 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1694-31-1 tert-butyl acetoacetate 
• 2537-98-6 C₁₆H₁₄N₄O₅ 
• 100-25-4 para-dinitrobenzene 
• 7647-01-0 hydrogenchloride 
• 2537-98-6 3-(4-nitro-anilino)-crotonic acid-(4-nitro-anilide) 
• 102-01-2 N-phenylacetoacetamide 

Downstream Products

• 2537-98-6 3-(4-nitro-anilino)-crotonic acid-(4-nitro-anilide) 
• 93010-04-9 (2-Hydroxy-5-sulfamoyl-phenylazo)-4-nitro-acetoacetanilid 
• 1373441-69-0 1,2,3,4-tetrahydro-6-methyl-N-(4-nitrophenyl)-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxamide 
• 1373441-68-9 1,2,3,4-tetrahydro-6-methyl-N-(4-nitrophenyl)-2-oxo-4-(1,3-diphenyl-1H-pyrazol-4-yl)pyrimidine-5-carboxamide 
• 1590368-29-8 5-methyl-N-(4-nitrophenyl)-1-[2-(phenylselanyl)phenyl]-1H-1,2,3-triazole-4-carboxamide 
• 1608483-66-4 8-bromo-4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 1608483-70-0 8-chloro-4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 
• 1608483-63-1 4-methyl-2-(4-nitrophenyl)-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione 

Relevant academic research and scientific papers

Synthesis and biological evaluation of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives

Two new series of thiazolo and imidazo N-(4-nitrophenyl)-7-methyl-5-aryl-pyrimidine-6 carboxamide derivatives were synthesized. All the synthesized compounds were evaluated for their antimicrobial activity against Gram-positive bacteria: Staphylococcus aureus MTCC 3160, Bacillus subtilis MTCC 441, Gram-negative bacterium: Escherichia coli MTCC 443 and antifungal activity against Candida albicans MTCC 227 and Aspergillus Niger MTCC 281 and free radical scavenging activity. Compound 7e was found the most active antimicrobial comparable to standards taken. Compounds 7a, 7c, 9a, and 9d also showed significant antibacterial and antifungal activity. Further, compounds 7f, 9d, and 9h showed significant antioxidant activity with IC50 comparable with the standard compound. The synthesized compounds were confirmed for their structure by means of various spectrometric techniques like IR, 1H NMR, mass, and elemental analysis.

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.

Novel 5-oxo-hexahydroquinoline derivatives: Design, synthesis, in vitro P-glycoprotein-mediated multidrug resistance reversal profile and molecular dynamics simulation study

Overexpression of the efflux pump P-glycoprotein (P-gp) is one of the important mechanisms of multidrug resistance (MDR) in many tumor cells. In this study, 26 novel 5-oxo-hexahydroquinoline derivatives containing different nitrophenyl moieties at C4 and various carboxamide substituents at C3 were designed, synthesized and evaluated for their ability to inhibit P-gp by measuring the amount of rhodamine 123 (Rh123) accumulation in uterine sarcoma cells that overexpress P-gp (MES-SA/Dx5) using flow cytometry. The effect of compounds with highest MDR reversal activities was further evaluated by measuring the alterations of MES-SA/Dx5 cells’ sensitivity to doxorubicin (DXR) using MTT assay. The results of both biological assays indicated that compounds bearing 2-nitrophenyl at C4 position and compounds with 4-chlorophenyl carboxamide at C3 demonstrated the highest activities in resistant cells, while they were devoid of any effect in parental nonresistant MES-SA cells. One of the active derivatives, 5c, significantly increased intracellular Rh123 at 100 μM, and it also significantly reduced the IC50 of DXR by 70.1% and 88.7% at 10 and 25 μM, respectively, in MES-SA/Dx5 cells. The toxicity of synthesized compounds against HEK293 as a noncancer cell line was also investigated. All tested derivatives except for 2c compound showed no cytotoxicity. A molecular dynamics simulation study was also performed to investigate the possible binding site of 5c in complex with human P-gp, which showed that this compound formed 11 average H-bonds with Ser909, Thr911, Arg547, Arg543 and Ser474 residues of P-gp. A good agreement was found between the results of the computational and experimental studies. The findings of this study show that some 5-oxo-hexahydroquinoline derivatives could serve as promising candidates for the discovery of new agents for P-gp-mediated MDR reversal.

Effective microwave synthesis of bioactive thieno[2,3-d]pyrimidines

A series of novel 2-Amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, 1H NMR and 13C NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.

Design, Multicomponent Synthesis and Characterization of Diversely Substituted Pyrazolo[1,5-a] Pyrimidine Derivatives

The synthesis of various heterocyclic compounds using acetoacetanilide[AAA], we have demonstrated that acetoactanilide are versatile intermediate for the synthesis of pyrazolopyrimidine derivatives. Thus, to explore further, we sought that the reaction of various acetoactanilide, an appropriate aldehyde and 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide in the presence of base in isopropyl alcohol could be an effective strategy to furnish the novel pyrazolopyrimidine derivatives. Here we describe the novel synthetic methodology for the fused pyrazolopyrimidines.

Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold

Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug-resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC-207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach - recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E-state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure-activity relationships that will guide the design of more potent inhibitors. This paper reports the second molecule after TMC-207, with the ability to inhibit tuberculosis bacilli in its dormant phase. The paper reports molecules with a novel Pyrimidone Scaffold, the synthesis of which was accomplished with a modified multi-component Biginelli reaction. A classification model was generated using recursive partitioning (RP) technique to identify structural characteristics of the molecules with their varying activities.

Dye compound, the compound containing a pigment dispersant, pigment composition, pigment dispersion and toner

PROBLEM TO BE SOLVED: To provide a pigment compound which improves the dispersibility of an azo pigment in a non-water-soluble solvent.SOLUTION: The pigment compound is represented by general formula (1), wherein Rrepresents 1-6C alkyl or phenyl; Rto Rrepresent H, LRor LRR(Lrepresents a divalent linking group; Lrepresents a trivalent linking group; and Rto Rrepresent ≥8C alkyl or ≥8C alkenyl), provided that at least one of Rto Ris LRor LRR; and Rto Rrepresent H, COORor CONRR(Rto Rrepresent H or 1-3C alkyl), provided that at least one of Rto Ris COORor CONRR.

Vinyl polymerizations of norbornene catalyzed by nickel complexes with acetoacetamide ligands

On the basis of a remote effect, a series of acetoacetamide ligands and corresponding nickel complexes N-(R-phenyl) acetoacetamide Ni(CH2Ph) (PMe3) (R = H, 1; R = 2-methyl, 2; R = 2,6-dimethyl, 3; R = 2,6-diisopropyl, 4; R = 4-NO2, 5) were synthesized and characterized. The solid structure of complex 3 was confirmed by X-ray single-crystal analysis to be of cis form. 1H and 31P NMR spectroscopy confirmed that cis and trans isomers of nickel complexes were present in solution. Norbornene polymerizations with acetoacetamide nickel complexes activated with modified methylaluminoxane (MMAO) were investigated in detail. Remote steric and electronic effects of acetoacetamide ligand on catalytic activity and molecular weight of polynorbornenes (PNBs) were observed. Characterizations of the obtained PNBs show that the obtained polymer products are non-crystalline vinylic-addition polynorbornenes. Copyright

NOVEL COMPOUND HAVING BISAZO DYE SKELETON, PIGMENT COMPOSITION CONTAINING THE SAME, PIGMENT DISPERSION, INK, AND COLOR FILTER RESIST COMPOSITION

The present invention provides a pigment dispersant that can improve the dispersion of an azo pigment in a water-insoluble solvent. The present invention relates to a compound having a bisazo moiety and a polyester moiety.

AZO COMPOUND, AND PIGMENT DISPERSANT, PIGMENT COMPOSITION, PIGMENT DISPERSION AND TONER COMPRISING AZO COMPOUND

There is provided a colorant compound improved in the dispersibility of an azo pigment into a water-insoluble solvent. The colorant compound is represented by the following general formula (1). R1 denotes an alkyl group having 1 to 6 carbon atoms, or a phenyl group; R2 to R6 each denote a hydrogen atom, or a substituent represented by the following general formula (2); R7 to R11 each denote a hydrogen atom, a COOR12 group, or a CONR13R14 group; and R12 to R14 each denote a hydrogen atom, or an alkyl group having 1 to 3 carbon atoms; and P1 denotes a polymeric component; L1 denotes an alkylene group having 1 to 3 carbon atoms or an arylene group having 6 to 10 carbon atoms; and * denotes a binding site.