1222-61-3Relevant academic research and scientific papers
Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
supporting information, p. 2019 - 2023 (2021/04/05)
Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
Accelerated Discovery of α-Cyanodiarylethene Photoswitches
Hecht, Stefan,K?nig, Niklas F.,Mutruc, Dragos
supporting information, p. 9162 - 9168 (2021/07/01)
Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.
α-Cyanostilbene based fluorophores: Aggregation-induced enhanced emission, solvatochromism and the pH effect
Palakollu, Veerabhadraiah,Kanvah, Sriram
, p. 5736 - 5746 (2015/02/19)
A series of α-cyanostilbenes substituted with dimethylaniline, diphenylaniline and carbazole was synthesized and their optical spectroscopic properties in homogeneous solvents, the dioxane-water binary mixture and the solid state were investigated. Stilbe
Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents
Alam, Mohammad Sayed,Nam, Young-Joo,Lee, Dong-Ung
, p. 790 - 797 (2013/10/22)
In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.
(Z)-2-(2-bromophenyl)-3-{[4-(1-methyl-piperazine)amino]phenyl}acrylonitrile (DG172): An orally bioavailable PPARβ/δ-selective ligand with inverse agonistic properties
Lieber, Sonja,Scheer, Frithjof,Meissner, Wolfgang,Naruhn, Simone,Adhikary, Till,Müller-Brüsselbach, Sabine,Diederich, Wibke E.,Müller, Rolf
supporting information; experimental part, p. 2858 - 2868 (2012/06/15)
The ligand-regulated nuclear receptor peroxisome proliferator-activated receptor β/δ (PPARβ/δ) is a potential pharmacological target due to its role in disease-related biological processes. We used TR-FRET-based competitive ligand binding and coregulator
Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases
D'Sa, Bosco A.,Kisanga, Philip,Verkade, John G.
, p. 3961 - 3967 (2007/10/03)
We report herein the use of 3-30 mol % of a new class of tricyclic strong nonionic Lewis bases P(MeNCH2CH2)3N and P(HNCH2CH2)(i-PrNCH2CH2) 2N for the direct catalytic synthesis of a variety of functionalized α,β-unsaturated nitriles in high yields from aldehydes and acetonitrile or benzyl cyanide at 40-50°C. Evidence for a novel mechanistic pathway proposed for this reaction in a polar protic solvent such as methanol, and a nonpolar aprotic solvent such as benzene is also presented. Under these conditions, primary and secondary aliphatic aldehydes do not condense satisfactorily with acetonitrile to give the α,β-unsaturated nitrile, and ketones do not condense with either benzyl cyanide or acetonitrile.
On the validity of the constants of ionic substituents. Substituent effects on the cyano stretching frequencies and intensities of trans-α-phenyl-β-arylacrylonitriles
Binev, Ivan,Velcheva, Evelina,Juchnovski, Ivan
, p. 1871 - 1878 (2007/10/02)
Fourier-transform IR frequencies υ(CN) and integrated intensities A(CN) of the cyano groups of a series of trans-α-phenyl-β-arylacrylonitriles (51 compounds) have been measured.Both υ(CN) and the square roots of A(C) of the neutral m- and p-su
