16313-65-8

Basic information

• Product Name: 5-NitroanthranilaMide
• Synonyms: 5-NitroanthranilaMide;2-CarbaMoyl-4-nitroaniline;NSC 142033
• CAS NO: 16313-65-8
• Molecular Formula: C₇H₇N₃O₃
• Molecular Weight: 181
• Product Categories: Amines;Aromatics;Intermediates
• Mol File: 16313-65-8.mol

Chemical Properties

• Melting Point: 236.4-237.0 °C
• Boiling Point: 358.8°Cat760mmHg
• Flash Point: 170.8°C
• Appearance: /
• Density: 1.481g/cm³
• Vapor Pressure: 2.48E-05mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO
• PKA: 14.63±0.50(Predicted)
• CAS DataBase Reference: 5-NitroanthranilaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NitroanthranilaMide(16313-65-8)
• EPA Substance Registry System: 5-NitroanthranilaMide(16313-65-8)

Safety Data

• Hazardous Substances Data: 16313-65-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-NitroanthranilaMide is used as an intermediate in the synthesis of nitro substituted quinazolones, which are important compounds in the pharmaceutical industry. These quinazolones have been found to possess a range of biological activities, including anti-cancer, anti-bacterial, and anti-viral properties. The use of 5-NitroanthranilaMide in the preparation of these quinazolones allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
5-NitroanthranilaMide is also used as a research compound in various chemical studies. Its unique chemical properties make it an ideal candidate for investigating the reactivity of nitroaniline derivatives and their potential applications in the synthesis of other organic compounds. Researchers can use 5-NitroanthranilaMide to explore new reaction pathways and develop innovative synthetic methods for the preparation of complex molecules.
Used in Dye Manufacturing:
Due to its yellow color, 5-NitroanthranilaMide can be used as a starting material in the production of various dyes and pigments. The nitro group in its structure can be reduced to form amino groups, which can then be used to synthesize a range of colored compounds. This makes 5-NitroanthranilaMide a valuable intermediate in the dye manufacturing industry, where it can be used to produce a variety of colors for use in textiles, plastics, and other applications.
Used in Analytical Chemistry:
5-NitroanthranilaMide can also be employed as a reagent in analytical chemistry for the detection and quantification of various substances. Its unique chemical properties allow it to form complexes with specific analytes, enabling the development of selective and sensitive analytical methods. This can be particularly useful in the detection of metal ions, organic compounds, and other substances in environmental, pharmaceutical, and industrial samples.

InChI:InChI=1/C7H7N3O3/c8-6-2-1-4(10(12)13)3-5(6)7(9)11/h1-3H,8H2,(H2,9,11)

Upstream product

• 41052-26-0 2-bromo-5-nitrobenzamide 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 17420-30-3 5-nitroanthranilonitrile 
• 616-79-5 2-amino-5-nitro-benzoic acid 
• 80887-01-0 2-bromo-5-nitrobenzoyl chloride 
• 943-14-6 2-bromo-5-nitrobenzoic acid 
• 4693-02-1 6-nitroisatoic anhydride 
• 118-48-9 isatoic anhydride 

Downstream Products

• 54166-78-8 ethyl {[2-(aminocarbonyl)-4-nitrophenyl]amino}(oxo)acetate 
• 24688-36-6 2-methyl-6-nitroquinazolin-4(3H)-one 
• 6943-17-5 6-nitroquinazolone 
• 344455-05-6 N⁴-[2-(4-chloro-phenyl)-ethyl]-quinazoline-4,6-diamine 
• 344455-02-3 EVP₁₄₈₀₉ 
• 691385-29-2 (6-nitro-quinazolin-4-yl)-phenethyl-amine 
• 663597-07-7 [2-(4-methoxy-phenyl)-ethyl]-(6-nitro-quinazolin-4-yl)-amine 
• 545380-34-5 NF-kB Activation Inhibitor 
• 545380-35-6 6-nitro-4-(4-phenoxyphenylethylamino)quinazoline 
• 157864-30-7 5-nitro-2-[N-(pyridin-3-ylcarbonyl)amino]benzamide 
• 1044872-27-6 2-(4-hydroxy-3,5-dimethyl-phenyl)-6-nitro-3H-quinazolin-4-one 
• 13324-84-0 6-nitro-2-phenyl-1,2-dihydroquinazolin-4(3H)-one 
• 24688-34-4 2-benzoyl-6-nitroquinazolin-4(3H)-one 

Relevant articles and documents

Synthesis, crystal structure, spectroscopic and photophysical studies of novel fluorinated quinazoline derivatives

A novel small library of seven fluorinated quinazoline derivatives was synthesized and for four of them, the crystal structures were solved by single X-ray diffractometer and compared the confirmation of molecules in solution-phase using 2D NOESY experiments. Taking advantage of the series prepared, we were able to describe the influence of various substituents on the core scaffold (fluorinated quinazoline) on its molecular conformations’ intermolecular interactions and on the photoluminescent properties. The Hirshfeld surfaces were used to investigate the structure-directing effects of functional groups in controlling their solid-state behavior. Theoretical DFT calculations were carried out for getting additional knowledge on crystal-state interactions as compared to a gas phase. The photo-physical (UV and fluorescence) properties of all compounds have been studied. among the series, five compounds exhibited excellent photoluminescent properties.

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L?1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L?1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.

Fluorescent biaryl uracils with C5-dihydro- And quinazolinone heterocyclic appendages in PNA

There has been much effort to exploit fluorescence techniques in the detection of nucleic acids. Canonical nucleic acids are essentially nonfluorescent; however, the modification of the nucleobase has proved to be a fruitful way to engender fluorescence. Much of the chemistry used to prepare modified nucleobases relies on expensive transition metal catalysts. In this work, we describe the synthesis of biaryl quinazolinone-uracil nucleobase analogs prepared by the condensation of anthranilamide derivatives and 5-formyluracil using inexpensive copper salts. A selection of modified nucleobases were prepared, and the effect of methoxy- or nitro- group substitution on the photophysical properties was examined. Both the dihydroquinazolinone and quinazolinone modified uracils have much larger molar absorptivity (~4-8×) than natural uracil and produce modest blue fluorescence. The quinazolinone-modified uracils display higher quantum yields than the corresponding dihydroquinazolinones and also show temperature and viscosity dependent emission consistent with molecular rotor behavior. Peptide nucleic acid (PNA) monomers possessing quinazolinone modified uracils were prepared and incorporated into oligomers. In the sequence context examined, the nitro-substituted, methoxy-substituted and unmodified quinazolinone inserts resulted in a stabilization (?Tm = +4.0/insert; +2.0/insert; +1.0/insert, respectively) relative to control PNA sequence upon hybridization to complementary DNA. All three derivatives responded to hybridization by the “turn-on” of fluorescence intensity by ca. 3-to-4 fold and may find use as probes for complementary DNA sequences.

A solvent- And catalyst-free tandem reaction: Synthesis, and photophysical and biological applications of isoindoloquinazolinones

An easy green synthetic approach for fused isoindoloquinazolinones has been developed under neat reaction (yields up to 91%) conditions. This new one-pot tandem methodology involves condensation of readily available anthranilamide with 3-(2-formylcycloalk

2 - Benzoyl -6 - amino -4 (3 H) - quinazolinone derivatives and their synthesis and use

The invention the invention relates to a 2 - benzoyl - 6 - amino - 4 (3 H) - quinazolinone derivative and its synthetic method and use, which belongs to the technical field of medicament, relates to the general formula (I), R1 , R2 ,

Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker against Meloidogyne incognita

To explore new skeleton with nematicidal activity, a series of novel 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker were synthesized and varied fragments were also introduced to increase structure diversity of the new skeleton. Their inhibitory activities in vivo were evaluated against Meloidogyne incognita. The newly prepared compounds A6, A8, A21, A28 and A38 exhibited more than 50% inhibition at the concentration of 20 mg/L. Especially compound A6 displayed 71.4% inhibition against Meloidogyne incognita at the concentration of 20 mg/L. The nematicidal activities varied significantly depending on the types and positions of the substituents, which provided guidance for further structure modification.

Chiral Phosphoric Acids in Metal–Organic Frameworks with Enhanced Acidity and Tunable Catalytic Selectivity

Chiral phosphoric acids are incorporated into indium-based metal–organic frameworks (In-MOFs) by sterically preventing them from coordination. This concept leads to the synthesis of three chiral porous 3D In-MOFs with different network topologies constructed from three enantiopure 1,1′-biphenol-phosphoric acid derived tetracarboxylate linkers. More importantly, all the uncoordinated phosphoric acid groups are periodically aligned within the channels and display significantly enhanced acidity compared to the non-immobilized acids. This facilitates the Br?nsted acid catalysis of asymmetric condensation/amine addition and imine reduction. The enantioselectivities can be tuned (up to '99 % ee) by varying the substituents to achieve a nearly linear correlation with the concentrations of steric bulky groups in the MOFs. DFT calculations suggest that the framework provides a chiral confined microenvironment that dictates both selectivity and reactivity of chiral MOFs.

2,4,6-Substituted Quinazolines with Extraordinary Inhibitory Potency toward ABCG2

Several members of the ABC transporter superfamily play a decisive role in the development of multidrug resistance (MDR) in cancer. One of these MDR associated efflux transporters is ABCG2. One way to overcome this MDR is the coadministration of potent in

Structure–activity relationships for inhibitors of Pseudomonas aeruginosa exoenzyme S ADP-ribosyltransferase activity

During infection, the Gram-negative opportunistic pathogen Pseudomonas aeruginosa employs its type III secretion system to translocate the toxin exoenzyme S (ExoS) into the eukaryotic host cell cytoplasm. ExoS is an essential in vivo virulence factor that enables P. aeruginosa to avoid phagocytosis and eventually kill the host cell. ExoS elicits its pathogenicity mainly via ADP-ribosyltransferase (ADPRT) activity. We recently identified a new class of ExoS ADPRT inhibitors with in vitro IC50 of around 20 μM in an enzymatic assay using a recombinant ExoS ADPRT domain. Herein, we report structure–activity relationships of this compound class by comparing a total of 51 compounds based on a thieno [2,3-d]pyrimidin-4(3H)-one and 4-oxo-3,4-dihydroquinazoline scaffolds. Improved inhibitors with in vitro IC50 values of 6 μM were identified. Importantly, we demonstrated that the most potent inhibitors block ADPRT activity of native full-length ExoS secreted by viable P. aeruginosa with an IC50 value of 1.3 μM in an enzymatic assay. This compound class holds promise as starting point for development of novel antibacterial agents.