5697-85-8

Usage

InChI:InChI=1/C14H15N/c15-14-9-5-4-8-13(14)11-10-12-6-2-1-3-7-12/h1-9H,10-11,15H2

Upstream product

• 52208-62-5 (Z)-2-nitrostilbene 
• 4264-29-3 (E)-2-nitrostilbene 
• 681461-50-7 N-(2-phenethylphenyl)benzamide 
• 62723-78-8 2-methoxymethylaniline 
• 1589-82-8 phenylmagnesium bromide 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 552-89-6 2-nitro-benzaldehyde 
• 4714-25-4 2-nitrostilbene 
• 13066-19-8 2-(2-phenylethenyl)benzenamine 
• 26216-91-1 2-phenyl-2,3-dihydro-1H-indole 
• 109-89-7 diethylamine 
• 164398-51-0 2-(2-Phenylethyl)phenyl azide 
• 27652-35-3 (E)-2-styrylaniline 
• 64-17-5 ethanol 

Downstream Products

• 7294-84-0 2-(2-phenylethyl)phenol 
• 776-35-2 9,10-dihydrophenanthrene 
• 35444-96-3 1-(2-iodophenyl)-2-phenylethane 
• 54888-53-8 2-acetamidobibenzyl 
• 681461-50-7 N-(2-phenethylphenyl)benzamide 
• 54888-58-3 C₂₁H₂₀N₂O₂S 
• 164398-51-0 2-(2-Phenylethyl)phenyl azide 
• 1259938-75-4 C₂₂H₁₆N₂O₄ 
• 1259938-74-3 C₂₂H₁₆N₂O₄ 
• 1174988-05-6 (E)-N-[3-chloro-1-ethylpyridin-4(1H)-ylidene]-2-phenethylaniline trifluoromethanesulfonate 
• 1186335-53-4 4,5,6,7-tetrachloro-N-[2'-(2-phenylethyl)phenyl]phthalimide 
• 84-11-7 9,10-phenanthrenequinone 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI50 of 22 ± 2 and 12 ± 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 μM, and 1.47 μM, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs.

"bulky-Yet-Flexible" α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air

To pursue a highly regioselective and efficient reductive Heck reaction, a series of moisture-and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the"bulky-yet-flexible"palladium complexes allowed highly anti-Markovnikov-selective hydroarylation of alkenes with (hetero)aryl bromides under aerobic conditions. Further synthetic application of the present protocol could provide rapid and straightforward access to functional and biologically active molecules.

Iron-Catalyzed Intramolecular Aminations of C(sp3)?H Bonds in Alkylaryl Azides

The nucleophilic iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of unactivated C(sp3)?H bonds in alkylaryl azides, which results in the formation of substituted indoline and tetrahydroquinoline derivatives.

Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists

Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (24 a), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound 24 a bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound 24 a appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists.

Catalytic, oxidant-free, direct olefination of alcohols using Wittig reagents

Reported here is the catalytic, acceptorless coupling of alcohols with in situ generated, non-stabilized phosphonium ylides to form olefins as major products. The reaction uses low catalyst loadings and does not require added oxidants. Hydrogenation of the product is minimized and the reaction leads to Z (aliphatic) or E (benzylic) stereospecificity.

Discovery and characterization of aryl isonitriles as a new class of compounds versus methicillin- and vancomycin-resistant Staphylococcus aureus

Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) have emerged as a global health concern. A new class of compounds featuring an aryl isonitrile moiety has been discovered that exhibits potent inhibitory activity against several clinically-relevant MRSA and VRSA isolates. Structure-activity relationship studies have been conducted to identify the aryl isonitrile group as the key functional group responsible for the observed antibacterial activity. The most potent antibacterial aryl isonitrile analogs (MIC 2 μM) did not show any toxicity against mammalian cells up to a concentration of 64 μM.

Diverting Hydrogenations with Wilkinson's Catalyst towards Highly Reactive Rhodium(I) Species

The addition of Barton's base has a dramatic effect on the classic rhodium(III)-mediated hydrogenations promoted by Wilkinson′s catalyst. Following the initial oxidative addition, a barrierless reductive elimination of HCl from the traditional rhodium(III) intermediates instantly produces a rhodium(I) monohydride species, which is remarkably reactive in the hydrogenation of several internal alkynes and functionalized trisubstituted alkenes. The direct formation of this species is unprecedented upon addition of molecular hydrogen and its catalytic potential has been hitherto barely explored.

Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles

The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.

Anti-influenza activity of phenethylphenylphthalimide analogs derived from thalidomide

Swine-origin influenza A virus has caused pandemics throughout the world and influenza A is regarded as a serious global health issue. Hence, novel drugs that will target these viruses are very desirable. Influenza A expresses an RNA polymerase essential for its transcription and replication which comprises PA, PB1, and PB2 subunits. We identified potential novel anti-influenza agents from a screen of 34 synthesized phenethylphenylphthalimide analogs derived from thalidomide (PPT analogs). For this screen we used a PA endonuclease inhibition assay, a PB2 pathogenicity-determinant domain-binding assay, and an anti-influenza A virus assay. Three PPT analogs, PPT-65, PPT-66, and PPT-67, were found to both inhibit PA endonuclease activity and retard the growth of influenza A, suggesting a correlation between their activities. PPT-28 was also found to inhibit the growth of influenza A. These four analogs have a 3,4-dihydroxyphenethyl group in common. We also discuss the possibility that 3,4-dihydroxyphenethyl group flexibility may play an important functional role in PA endonuclease inhibition. Another analog harboring a dimethoxyphenethyl group, PPT-62, showed PB2 pathogenicity-determinant domain-binding activity, but did not inhibit the growth of the virus. Our present results indicate the utility of the PA endonuclease assay in the screening of anti-influenza drugs and are therefore useful for future strategies to develop novel anti-influenza A drugs and for mapping the function of the influenza A RNA polymerase subunits.

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.