6953-81-7

Usage

InChI:InChI=1/C12H12N2O2/c1-13(2)9-3-5-10(6-4-9)14-11(15)7-8-12(14)16/h3-8H,1-2H3

Upstream product

• 19392-50-8 N-(p-Dimethylaminophenyl)-9,10-dihydro-9,10-ethanoanthracen-11,12-dicarboximid 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 6957-55-7 N-(4-dimethylamino-phenyl)-maleamic acid 

Downstream Products

• 70650-06-5 5-(4-dimethylamino-phenyl)-2,3ξ-diphenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-59-4 3ξ-(4-bromo-phenyl)-5-(4-dimethylamino-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-62-9 5-(4-dimethylamino-phenyl)-3ξ-(4-nitro-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 70464-60-7 3ξ,5-bis-(4-dimethylamino-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 76085-75-1 C₄₃H₃₄N₂O₅ 
• 76085-94-4 C₄₁H₂₈Cl₂N₂O₃ 
• 76085-84-2 C₄₃H₃₄N₂O₃ 
• 70464-61-8 5-(4-dimethylamino-phenyl)-3ξ-(4-methoxy-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 

Relevant academic research and scientific papers

Identification of two arylimides as cholinesterase inhibitors and testing of propranolol addition on impaired rat memory

Alzheimer's disease (AD) is clearly linked to the decline of acetylcholine (ACh) effects in the brain. These effects are regulated by the hydrolytic action of acetylcholinesterase (AChE). Therefore, a central palliative treatment of AD is the administration of AChE inhibitors although additional mechanisms are currently described and tested for generating advantageous therapeutic strategies. In this work, we tested new arylamides and arylimides as potential inhibitors of AChE using in silico tools. Then, these compounds were tested in vitro, and two selected compounds, C7 and C8, as well as propranolol showed inhibition of AChE. In addition, they demonstrated an advantageous acute toxicity profile compared to that of galantamine as a reference AChE inhibitor. in vivo evaluation of memory performance enhancement was performed in an animal model of cognitive disturbance with each of these compounds and propranolol individually as well as each compound combined with propranolol. Memory improvement was observed in each case, but without a significant additive effect with the combinations.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.

Photoactivatable anthracenes

Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.