13278-39-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-BROMO-PHENYLAMINO)-BENZOIC ACID is used as an intermediate in the synthesis of various pharmaceutical drugs for its ability to form versatile organic molecules due to the presence of bromine and amino groups.
It is important to handle 2-(3-BROMO-PHENYLAMINO)-BENZOIC ACID with care, as it may have potential hazards associated with its handling and use.

Upstream product

• 1488-42-2 Diphenyliodonium-2-carboxylate 
• 591-19-5 m-Bromoaniline 
• 134-20-3 2-carbomethoxyaniline 
• 108-36-1 1,3-dibromobenzene 
• 88-67-5 2-Iodobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 16497-87-3 potassium o-bromobenzoate 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 1621107-09-2 C₁₄H₁₄BrNO 
• 1621106-97-5 2-((3-bromophenyl)(methyl)amino)benzaldehyde 
• 1621107-02-5 methyl 2-((3-bromophenyl)(methyl)amino)benzoate 
• 1422034-74-9 1-(N-(2-aminoacetaniline))-10-methylacridone 
• 1370454-63-9 methyl 3-(1-bromoacridin-9-ylthio)benzoate 
• 1370454-58-2 4-(1-bromoacridin-9-ylthio)phenol 
• 1370454-39-9 1-bromo-9-(3-methoxyphenylthio)acridine 
• 1370454-34-4 1-bromo-9-(4-methoxyphenylthio)acridine 
• 1370454-32-2 N-(4-(1-bromoacridin-9-yloxy)phenyl)acetamide 
• 1370454-90-2 methyl 4-(1-bromoacridin-9-ylthio)benzoate 
• 88280-58-4 N-(3-bromo-N-phenylaniline) 

Relevant academic research and scientific papers

Effect of the substituent position on the electrochemical, optical and structural properties of donor-acceptor type acridone derivatives

Three new donor-acceptor (D-A) compounds, positional isomers of phenoxazine-substituted acridone, namely 1-phenoxazine-N-hexylacridone ( o-A ), 2-phenoxazine-N-hexylacridone ( m-A ) and 3-phenoxazine-N-hexylacridone ( p-A ), were synthesized. The synthesized compounds showed interesting, isomerism-dependent electrochemistry. Their oxidation was reversible and their potential (givenvs.Fc/Fc+) changed from 0.21 V for o-A to 0.36 V for p-A . In contrast, their reduction was irreversible, isomerism-independent and occurred at rather low potentials (ca.?2.25 to ?2.28 V). The electrochemical results led to the following values of the ionization potentials (IPs) and electron affinities (EAs): 5.03 eV and ?2.14 eV, 5.15 eV and ?2.20 eV, and 5.20 eV and ?2.28 eV for o-A m-A and p-A , respectively. The experimentally obtained values were in very good agreement with those predicted by DFT calculations. All three isomers readily formed single crystals suitable for their structure determination. o-A and p-A crystallized inP1? andP21/nspace groups, respectively, with one molecule per asymmetric unit, while m-A crystallized in theP21/cspace group with two molecules in the asymmetric unit accompanied by disordered solvent molecules. The UV-vis spectra of the studied compounds were isomerism and solvent independent, yielding absorption maxima in the vicinity of 400 nm. Their photoluminescence spectra, in turn, strongly depended on isomerism and the used solvent showing smaller Stokes shifts for the emission bands registered in toluene as compared to the corresponding bands measured in dichloromethane. The photoluminescence quantum yields (?) were systematically higher for toluene solutions reaching the highest value of 20% for p-A . For all three isomers studied, stationary and time-resolved spectroscopic investigations carried out in toluene at different temperatures revealed spectral features indicating a contribution of thermally activated delayed fluorescence (TADF) to the observed spectroscopic behaviour. The measured photoluminescence quantum yields (?) were higher for solid state films of pure compounds and for their dispersions in solid matrices (zeonex) than those recorded for toluene and dichloromethane solutions of the studied phenoxazine-N-hexylacridone isomers. The obtained experimental spectroscopic and structural data were confronted with theoretical predictions based on DFT calculations.

Design, synthesis and bioactivity evaluation of novel evodiamine derivatives with excellent potency against gastric cancer

Gastric cancer represents a significant health burden worldwide. Previously, inspired by the traditional Chinese medicine Wu-Chu-Yu to treat the spleen and stomach system for thousands of years, we identified N14-phenyl substituted evodiamine derivatives as potential antitumor agents with favorable inhibition on Top1. Herein, structural optimization and structure-activity relationship studies (SARs) led us to discovering a highly active evodiamine derivative compound 6t against gastric cancer. Further anti-tumor mechanism studies revealed that compound 6t played as the inhibition of topoisomerase 1 (Top1), effectively induced apoptosis, obviously arrested the cell cycle at the G2/M phase, and significantly inhibited the migration and invasion of SGC-7901 and MGC-803 cell lines in a dose-dependent manner. Moreover, the compound 6t was low toxicity in vivo and exhibited excellent anti-tumor activity (TGI = 70.12%) in the MGC-803 xenograft models. In summary, compound 6t represents a promising candidate as a potential chemotherapeutic agent against gastric cancer.

Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents

Natural products are important sources for the development of therapeutic medicine, among which evodia fruit has a wide range of medicinal properties in traditional Chinese medicine. Evodiamine, the main active component of evodia fruit, has various anti-cancer effects and has been proved to be a Topo inhibitor. From our previous attempts of modifying evodiamine, we found that the N14 phenyl substituted derivatives had showed great anti-tumor activity, which prompted us to further explore the novel structures and activities of these compounds. Compound 6f, as a N14 3-fluorinated phenyl substituted evodiamine derivative, showed a certain inhibitory activity against Topo I at 200 μM. By studying its anti-tumor effects in vitro, compound 6f could inhibit proliferation and induce apoptosis, as well as arrest the cell cycle of HGC-27 and HT-29 cell lines at G2/M phase in a concentration-dependent manner. Moreover, compound 6f could inhibit the migration and invasion of HGC-27 cell lines. Meanwhile, compound 6f could induce apoptosis of HGC-27 cells by inhibiting PI3K/AKT pathway. Overall, this work demonstrated that the N14 phenyl-substituted evodiamine derivatives had a good inhibitory effect on tumor cells in vitro, providing a promising strategy for developing potential anticancer agents for the treatment of gastrointestinal tumors.

Design, synthesis and biological evaluation of N-anthraniloyl tryptamine derivatives as pleiotropic molecules for the therapy of malignant glioma

COX-2 and STAT3 are two key culprits in the glioma microenvironment. Herein, to inhibit COX-2 and block STAT3 signaling, we disclosed 27 N-anthraniloyl tryptamine compounds based on the combination of melatonin derivatives and N-substituted anthranilic acid derivatives. Among them, NP16 showed the best antiproliferative activity and moderate COX-2 inhibition. Of note, NP16 decreased the level of p-JAK2 and p-STAT3, and blocked the nuclear translocation of STAT3 in GBM cell lines. Moreover, NP16 downregulated the MMP-9 expression of BV2 cells in a co-culture system of BV2 and C6 glioma cells, abrogated the proliferative/invasive/migratory abilities of GBM cells, induced apoptosis by ROS and the Bcl-2-regulated apoptotic pathway, and induced obvious G2/M arrest in glioma cells in vitro. Furthermore, NP16 displayed favorable pharmacokinetic profiles covering long half-life (11.43 ± 0.43 h) and high blood-brain barrier permeability. Finally, NP16 effectively inhibited tumor growth, promoted the survival rate, increased the expression of E-cadherin and reduced overproduction of PGE2, MMP-9, VEGF-A and the level of p-STAT3 in tumor tissue, and improved the anxiety-like behavior in C6 glioma model. All these evidences demonstrated N-anthraniloyl tryptamine derivatives as multifunctional anti-glioma agents with high potency could drain the swamp to beat glioma.

Novel organic compound and organic electroluminescent device comprising novel organic compound

The invention provides an organic compound represented by a following chemical formula A, wherein R to R, L, Ar, Ar, X, m, n and k are defined as in the protection scope of the invention.

THE NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME

Provided is an organic compound represented by the chemical formula a. In the chemical formula a, R_1 to R_3, L, Ar_1, Ar_2, X, m, n and k are the same as defined. One embodiment of the present invention provides a novel organic compound having appropriate energy levels, electrochemical stability, and thermal stability.COPYRIGHT KIPO 2018

Structure-Polymorphism Study of Fenamates: Toward Developing an Understanding of the Polymorphophore

The ability of molecules to adopt more than one unique crystalline structure, polymorphism, is a phenomenon of considerable scientific interest because it challenges the notion that molecules arrange themselves exclusively in the thermodynamically most stable crystal form. The factors influencing this behavior are manifold and have defied simple prediction. To illustrate an approach to elucidating these factors, the solid-state behavior of a series of molecules that are derivatives of tolfenamic acid (TA), a pentamorphic system, was explored. In analogy to the manner in which drugs are discovered through structure-activity relationships and the identification of a pharmacophore, we test here the notion that when a collective ensemble structural motifs, a "polymorphophore," is incorporated into a molecule it renders the compound polymorphic. The structure-polymorphism relationship in six TA analogues, both commercial and newly synthesized, was undertaken with the intention of systematically understanding the factors that influence the polymorphism in the fenamic acid class through a combined computational as well as experimental approach. Ultimately, such studies may be used to experimentally derive the propensity for polymorphic behavior of a given molecular motif and perhaps provide a pathway to engineer molecular compounds with controlled properties in the solid state.

PhI(OAc)2-mediated intramolecular oxidative aryl-aldehyde C sp 2-C sp 2 bond formation: Metal-free synthesis of acridone derivatives

A metal-free protocol for direct aryl-aldehyde Csp2-Csp 2 bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines

A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).

N8, n13 -disubstituted quino[4,3,2-kl]acridinium salts as therapeutic agents

The present invention pertains to certain N8,N13-disubstituted quino[4,3,2-kl]acridinium salts of formula (Q?) which inhibit telomerase wherein: p is an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 4; each RA is —H or a ring substituent; each RB is —H or a ring substituent; each RC is —H or a ring substituent; RN8 is a nitrogen substituent; RN13 is a nitrogen substituent; and, Q is an anion. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell proliferation, and in the treatment of proliferative conditions, such as cancer.