91-42-9

Usage

Organic compound

It is an organic compound because it is primarily composed of carbon atoms along with hydrogen, nitrogen, and oxygen atoms.

Benzene ring structure

The compound has a benzene ring as its core structure, which is a six-membered aromatic ring with alternating single and double bonds.

Methoxy group

A methoxy group (-OCH3) is attached to the benzene ring, which consists of an oxygen atom bonded to a methyl group (-CH3).

Amino group

An amino group (-NH2) is also attached to the benzene ring, which is a nitrogen atom bonded to two hydrogen atoms.

Nitro group

A nitro group (-NO2) is another substituent on the benzene ring, consisting of an oxygen atom double-bonded to a nitrogen atom.

Potential biological activity

2-(4-Methoxy-phenylamino)-4-nitro-benzoic acid has potential biological activity, meaning it may interact with biological systems and have pharmacological effects.

Medicinal properties

The compound may possess medicinal properties, making it a candidate for use in the development of new drugs or therapies.

Building block for other chemical compounds

Due to its unique structure and functional groups, 2-(4-Methoxy-phenylamino)-4-nitro-benzoic acid can be used as a building block or intermediate in the synthesis of other chemical compounds.

Valuable tool in organic chemistry research

The compound's properties and behavior in various chemical reactions make it a valuable tool for researchers in the field of organic chemistry, aiding in the development of new synthetic methods and the study of reaction mechanisms.

InChI:InChI=1/C14H12N2O5/c1-21-11-5-2-9(3-6-11)15-13-8-10(16(19)20)4-7-12(13)14(17)18/h2-8,15H,1H3,(H,17,18)

Upstream product

• 99-60-5 2-chloro-4-nitrobenzoic acid 
• 104-94-9 4-methoxy-aniline 
• 16426-64-5 2-bromo-4-nitrobenzoic acid 
• 100959-22-6 methyl 2-bromo-4-nitrobenzoate 
• 118210-83-6 C₁₅H₁₄N₂O₅ 

Downstream Products

• 195370-43-5 C₁₅H₁₅N₅O₄S 
• 15463-20-4 (2-methoxy-6-nitro-acridin-9-yl)-(4-methoxy-phenyl)-amine 

Relevant academic research and scientific papers

A highly acidic acridine for efficient site-selective activation of RNA leading to an eminent ribozyme mimic

9-Amino-2-methoxy-6-nitroacridine (1a) is conjugated with oligonucleotide for site-selective RNA hydrolysis. When this conjugate forms a duplex with complementary RNA, the phosphodiester linkage of the RNA in front of 1a is activated and selectively hydro

Development of WNK signaling inhibitors as a new class of antihypertensive drugs

Pseudohypoaldosteronism type II (PHAII) is characterized by hyperkalemia and hypertension despite a normal glomerular filtration rate. Abnormal activation of the signal cascade of with-no-lysine kinase (WNK) with OSR1 (oxidative stress-responsive kinase 1)/SPAK (STE20/SPS1-related proline/alanine-rich kinase) and NCC (NaCl cotransporter) results in characteristic salt-sensitive hypertension. Thus, inhibitors of the WNK-OSR1/SPAK-NCC cascade are candidates for a new class of antihypertensive drugs. In this study, we developed novel inhibitors of this signal cascade from the 9-aminoacridine lead compound 1, one of the hit compounds obtained by screening our chemical library for WNK-SPAK binding inhibitors. Among the synthesized acridine derivatives, several acridine-3-amide and 3-urea derivatives, such as 10 (IC50: 6.9?μM), 13 (IC50: 2.6?μM), and 20 (IC50: 4.8?μM), showed more potent inhibitory activity than the lead compound 1 (IC50: 15.4?μM). Compounds 10 and 20 were confirmed to inhibit phosphorylation of NCC in vivo.

Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment

Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 μM, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors.

A rapid, chromatography-free route to substituted acridine-isoalloxazine conjugates under microwave irradiation

Microwave irradiation was applied to a sequence of condensation reactions from readily available 9-chloroacridines to provide a range of novel acridine-isoalloxazine conjugates. The combination of these two moieties, both of biological interest, was achieved by a chromatography-free route.

Monna, a potent and selective blocker for transmembrane protein with unknown function 16/anoctamin-1

Transmembrane protein with unknown function 16/anoctamin-1 (ANO1) is a protein widely expressed in mammalian tissues, and it has the properties of the classic calcium-activated chloride channel (CaCC). This protein has been implicated in numerous major physiological functions. However, the lack of effective and selective blockers has hindered a detailed study of the physiological functions of this channel. In this study, we have developed a potent and selective blocker for endogenous ANO1 in Xenopus laevis oocytes (xANO1) using a drug screening method we previously established (Oh et al., 2008). We have synthesized a number of anthranilic acid derivatives and have determined the correlation between biological activity and the nature and position of substituents in these derived compounds. A structure-activity relationship revealed novel chemical classes of xANO1 blockers. The derivatives contain a-NO2 group on position 5 of a naphthyl group-substituted anthranilic acid, and they fully blocked xANO1 chloride currents with an IC 5050 of 0.08 μM for xANO1. Selectivity tests revealed that other chloride channels such as bestrophin-1, chloride channel protein 2, and cystic fibrosis transmembrane conductance regulator were not appreciably blocked by 10～30 μM MONNA. The potent and selective blockers for ANO1 identified here should permit pharmacological dissection of ANO1/CaCC function and serve as potential candidates for drug therapy of related diseases such as hypertension, cystic fibrosis, bronchitis, asthma, and hyperalgesia.

Regioselective copper-catalyzed amination of chlorobenzoic acids: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives

A chemo- and regioselective copper-catalyzed cross-coupling reaction for effective amination of 2-chlorobenzoic acids with aniline derivatives has been developed. The method eliminates the need for acid protection and produces a wide range of N-aryl anthranilic acid derivatives in up to 99% yield. The amination was found to proceed with both electron-rich and electron-deficient aryl chlorides and anilines and also utilizes sterically hindered anilines such as 2,6-dimethylaniline and 2-tert-butylaniline. The conformational isomerism of appropriately substituted N-aryl anthranilic acids has been investigated in the solid state. Crystallographic analysis of seven anthranilic acid derivatives showed formation of two distinct supramolecular architectures exhibiting trans-anti and unprecedented trans-syn dimeric structures.

Fast synthesis of substituted N-phenylanthranilic acids using Ullmann condensation under microwave irradiation in dry media

Substituted N-phenylanthranilic acids using the Ullmann condensation under microwave irradiation in dry media were obtained in good yield and short reaction times. Copyright Taylor & Francis LLC.

Microwave-assisted synthesis of N-phenylanthranilic acids in water

N-Phenylanthranilic acid derivatives were synthesised using the Ullmann condensation of 2-chlorobenzoic acid with aniline derivatives under microwave irradiation in aqueous media. The method offers better yields in shorter reaction times compared to classical heating approaches using water as solvent.

Convenient access to substituted acridines by a Buchwald-Hartwig amination

A convenient, high yield procedure for the synthesis of anthranilic acids carrying a variety of different substituents as well as their straightforward transformation into the corresponding 9-chloroacridines could be established by using modified Buchwald-Hartwig amination conditions.

Synthesis and antitumor activity of 9-anilino, phenylhydrazino, and sulphonamido analogs of 2- or 4-methoxy-6-nitroacridines

Synthesis of several new 9-anilino, phenylhydrazino, and sulphonamido analogs of 2- or 4-methoxy-6-nitroacridine derivatives is described. The prepared compounds were tested for their in vitro antitumor activity against 60 human tumor cell lines by the National Cancer Institute (NCI) and showed a potential anticancer activity. Compounds 9-(phenylhydrazino)-2-methoxy-6-nitroacridine (8a) and 9-(4-chlorophenylhydrazino)-4-methoxy-6-nitroacridine (9b) exhibited a broad spectrum antitumor activity with full panel (MG-MID) median growth inhibition(GI50), of 16.1 and 10.9 μM and total growth inhibition (TGI) of 66.7 and 37.9 μM, respectively. Meanwhile, compounds 15a and 15b showed moderate selectivity toward leukemia cell lines. As a trial to explore the mode of action of their antitumor activity, the 6-nitroacridine analogs were evaluated for their inhibitory effect on major cell cycle control proteins cdc2 kinase and cdc25 phosphatase as possible molecular targets that may account for antimitotic potency. None of the tested compounds proved to exert their activity via this antimitotic mode of action.