4439-55-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-furylmethyl)-N-(2-phenylethyl)amine is used as a key intermediate in the synthesis of carboxamido-isoindolinone derivatives, which are selective PARP-1 inhibitors. These inhibitors play a crucial role in the development of targeted therapies for cancer treatment, as they can modulate the activity of poly(ADP-ribose) polymerase-1 (PARP-1), an enzyme involved in DNA repair and cell survival pathways. By inhibiting PARP-1, these derivatives can enhance the effectiveness of DNA-damaging agents and improve the outcomes for patients with certain types of cancer.

InChI:InChI=1/C13H15NO/c1-2-5-12(6-3-1)8-9-14-11-13-7-4-10-15-13/h1-7,10,14H,8-9,11H2

Upstream product

• 69819-53-0 furfural-phenethylimine 
• 617-89-0 furan-2-ylmethanamine 
• 103-63-9 1-phenyl-2-bromoethane 
• 69819-53-0 N-(2-furylmethylidene)-2-phenylethylamine 
• 98-01-1 furfural 
• 64-04-0 phenethylamine 

Downstream Products

• 77960-22-6 4-oxo-3-phenethyl-10-oxa-3-azatricyclo[5.2.1.0^1,5]dec-8-ene-6-carboxylic acid 
• 77960-22-6 C₁₇H₁₇NO₄ 
• 1429934-24-6 C₂₈H₂₈N₂O₂S₄Zn 
• 1429934-27-9 C₃₈H₃₆N₄O₂S₄Zn 
• 1403502-02-2 bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S')lead(II) 
• 943251-45-4 3-oxo-2-phenethyl-2,3-dihydro-1H-isoindole-5-carboxylic acid 

Relevant academic research and scientific papers

Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations

Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.

Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy

The nuclear protein poly(ADP-ribose) polymerase-1 (PARP-1) has a well-established role in the signaling and repair of DNA and is a prominent target in oncology, as testified by the number of candidates in clinical testing that unselectively target both PARP-1 and its closest isoform PARP-2. The goal of our program was to find a PARP-1 selective inhibitor that would potentially mitigate toxicities arising from cross-inhibition of PARP-2. Thus, an HTS campaign on the proprietary Nerviano Medical Sciences (NMS) chemical collection, followed by SAR optimization, allowed us to discover 2-[1-(4,4-difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118, 20by). NMS-P118 proved to be a potent, orally available, and highly selective PARP-1 inhibitor endowed with excellent ADME and pharmacokinetic profiles and high efficacy in vivo both as a single agent and in combination with Temozolomide in MDA-MB-436 and Capan-1 xenograft models, respectively. Cocrystal structures of 20by with both PARP-1 and PARP-2 catalytic domain proteins allowed rationalization of the observed selectivity.

Synthesis, spectral and X-ray structural studies on Hg(II) dithiocarbamate complexes: A new precursor for HgS nanoparticles

Bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S′)mercury(II) (1), bis((furan-2-yl)methyl(2-(thiophen-2-yl)ethyl)dithiocarbamato-S,S′)mercury(II) (2), bis(N-benzyl-N-(2-(thiophen-2-yl)ethyl)dithiocarbamato-S,S′)mercury(II) (3) and bis(N-furfuryl-N-prop

Development and optimization of piperidyl-1,2,3-triazole ureas as selective chemical probes of endocannabinoid biosynthesis

We have previously shown that 1,2,3-triazole ureas (1,2,3-TUs) act as versatile class of irreversible serine hydrolase inhibitors that can be tuned to create selective probes for diverse members of this large enzyme class, including diacylglycerol lipase-β (DAGLβ), a principal biosynthetic enzyme for the endocannabinoid 2-arachidonoylglycerol (2-AG). Here, we provide a detailed account of the discovery, synthesis, and structure-activity relationship (SAR) of (2-substituted)-piperidyl-1,2,3-TUs that selectively inactivate DAGLβ in living systems. Key to success was the use of activity-based protein profiling (ABPP) with broad-spectrum and tailored activity-based probes to guide our medicinal chemistry efforts. We also describe an expanded repertoire of DAGL-tailored activity-based probes that includes biotinylated and alkyne agents for enzyme enrichment coupled with mass spectrometry-based proteomics and assessment of proteome-wide selectivity. Our findings highlight the broad utility of 1,2,3-TUs for serine hydrolase inhibitor development and their application to create selective probes of endocannabinoid biosynthetic pathways.

Synthesis, characterization, cytotoxicity and antimicrobial studies on bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S')zinc(II) and its nitrogen donor adducts

[Zn(fpedtc)2] (1), [Zn(fpedtc)2(py)] (2), [Zn(fpedtc)2(1,10-phen)] (3) and [Zn(fpedtc)2(2,2′- bipy)] (4) (where fpedtc = N-furfuryl-N-(2-phenylethyl)dithiocarbamate, py = pyridine, 1,10-phen = 1,10-phenanthrolin

Synthesis and spectral studies on Pb(II) dithiocarbamate complexes containing benzyl and furfuryl groups and their use as precursors for PbS nanoparticles

Nine lead bis(dithiocarbamate) complexes based on benzyl and furfuryl groups have been prepared. The complexes were characterized using IR and NMR spectroscopy. All the complexes showed the expected signals in 1H and 13C NMR spectra associated with the dithiocarbamate ligands. IR and 13C NMR spectral studies indicate that the S2CN double bond character increases with increase in length of alkyl chain bonded to nitrogen atom. Bis(N-benzyl-N-(2-phenylethyl)dithiocarbamato-S,S′)lead(II) (3) and bis(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S′)lead(II) (4) have been used as single source precursors for the synthesis of ethylenediamine capped PbS nanoparticles. Powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), FTIR, UV-vis and fluorescence spectroscopy have been used to characterize the as-prepared lead sulfide nanoparticles. The PXRD measurements suggest that PbS nanoparticles are single phase with face-centered-cubic structure.

Synthesis of advanced intermediates of lennoxamine analogues

A simple and convenient method for synthesis of advanced isoindolone intermediates of lennoxamine and analogues is described in this paper. The intramolecular Diels-Alder reaction of furan is used as a key step in this synthesis. Georg Thieme Verlag Stuttgart.

SYNTHETIC BIOREGULATORS OF POLY-CIS CAROTENOID BIOSYNTHESIS

Seventeen new bioregulators were synthesized and tested for their ability to induce the biosynthesis of poly-cis carotenes in the flavedo of Marsh white seedless grapefruit.The effects of these new bioregulators are the same as that of the previously reported dibenzylamines, but several of the new compounds are more effective and cause the accumulation of up to 162 μg/g dry wt of poly-cis carotenes in the flavedo as compared to the maximum of 74 μg/g dry wt observed previously.The compounds tested were substituted N-benzyl furfurylamines, N-benzyl, N-methyl furfurylamines and N-alkyl , N-methyl benzylamines.They demonstrate the ability of tertiary as well as secondary amines to stimulate the formation of poly-cis carotenes.The interaction of N-(4-bromobenzyl) furfurylamine, one of the more effctive of the new compounds, with lycopene and β-carotene inducers is also reported.Key Word Index - Citrus paradisi; Rutaceae; Marsh white seedles grapefruit; carotenoid biosynthesis; bioregulators; secondary amines; poly-cis carotenoids; prolycopene.