99232-57-2

Upstream product

• 612-23-7 2-nitrobenzyl chloride 
• 108-95-2 phenol 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 612-25-9 2-Nitrobenzyl alcohol 

Downstream Products

• 103200-10-8 C₁₅H₁₁⁽²⁾H₆NO 
• 321534-84-3 4-hydroxy-2-methyl-quinoline-6-carboxylic acid (2-phenoxymethyl-phenyl)-amide 
• 321534-85-4 4-methoxyquinoline-6-carboxamide 
• 78584-41-5 (o-Aminobenzyl)-phenyl-ether 

Relevant academic research and scientific papers

Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition

Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.

Synthesis of substituted 6H-benzo[c]chromenes: A palladium promoted ring closure of diazonium tetrafluoroborates

A highly efficient palladium-catalysed phenyl diazonium tetrafluoroborate participation of C-H activation ring closure protocol has been developed. A series of 6H-benzo[c]chromenes have been synthesized by intramolecular cyclization of ortho diazonium sal

Highly activatable and environment-insensitive optical highlighters for selective spatiotemporal imaging of target proteins

Optical highlighters are photoactivatable fluorescent molecules that exhibit pronounced changes in their spectral properties in response to irradiation with light of a specific wavelength and intensity. Here, we present a novel design strategy for a new class of caged BODIPY (4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene) fluorophores, based on the use of photoremovable protecting groups (PRPGs) with high reduction potentials that serve as both a photosensitive unit and a fluorescence quencher via photoinduced electron transfer (PeT). 2,6-Dinitrobenzyl (DNB)-caged BODIPY was efficiently photoactivated, with activation ratios exceeding 600-fold in aqueous solutions. We then combined this photoactivatable fluorophore with a SNAP (mutant of O 6-alkylguanine DNA alkyltransferase) ligand to obtain a small-molecule-based optical highlighter for visualization of protein dynamics, using the well-established SNAP tag technology. As proof of concept, we demonstrate spatiotemporal imaging of the fusion protein of epidermal growth factor receptor (EGFR) with SNAP tag in living cells. We also demonstrate highlighting of cells of interest in live zebrafish embryos, using the fusion protein of histone 2A with SNAP tag.

4-Aminoquinolines: Novel nociceptin antagonists with analgesic activity

Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure - Activity relationships eventually led to the optimum compounds. One of these compounds, N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from μ-opioid agonists.

Nitrobenzyl esters as potential conjugated alkylating and differentiation promoting agents: Antitumor effect in vivo

A series of ortho and para-nitrobenzyl esters of short chain fatty acids (C2 to C5) and of the lipophilic aminoacid, L-valine, and some other o-nitrobenzylated products were prepared. Bioreductive or hydrolytic cleavages of these compounds could release both differentiation promoting agents such as butyric acid and electrophilic moieties able to alkylate DNA. The antitumor effects of these compounds, either alone and/or associated with an immunostimulating agent (corynebacterium parvum, CP) or interferon (IFN) treatment, was studied using the 180 TG Crocker Sarcoma grafted onto Swiss mice. Based on the mean survival time and the final survival rate, the most active compounds used alone were the o-nitrobenzyl acetate and the 0-nitrobenzyl butyrate. Previous stimulation of the immune competent cells by CP before antitumor treatment increased the efficiency of most of the nitrobenzylated derivatives studied. The association with IFN did not significantly improve the antitumor effect.

Gas Phase Generation and Reactions of o-Dialkylaminobenyzl and o-Dialkylaminophenoxyl Radicals

Generation of the title radicals was effected by flash vacuum pyrolysis of benzyl phenyl ethers, and O-allyl ethers, respectively.The major products are formed by a multi-step sequence involving (i) intramolecular hydrogen transfer from the alkylamino group to the initial radical cemtre, (ii) rearrangement of the resulting aminoalkyl radical, (iii) expulsion of the nitrogen residue to give a bezyl radical which leads to products.