Potential antiatherosclerotic agents. 6. Hypocholesterolemic trisubstituted urea analogs

Abstract

The discovery that a series of N,N-dialkyl-N'-arylureas were inhibitors of the ACAT enzyme has led to a structure-activity study involving the systematic modification of three sites of the urea backbone. This study culminated in the selection of N'-(2,4-dimethylphenyl)-N-benzyl-N-n-butylurea (115) for more extensive biological evaluation. ACAT inhibitors are seen as potentially beneficial agents against hypercholesterolemia and atherosclerosis.

One-Pot Synthesis of Novel Dibenzoxanthenes, Diarylbutanes, and Calix[4]resorcinarenes via Consecutive Pyrrolidine Ring-Closure/Ring-Opening Reactions

“…1 H NMR spectra were recorded on a Bruker MSL 400 spectrometer (400 MHz) with respect to the signals of residual protons of deuterated solvent (DMSO-d 6 ). 13 C NMR spectra were recorded on a Bruker Avance 600 (150 MHz) spectrometer relative to signals of residual protons of deuterated solvent (DMSO-d 6 ). MALDI mass-spectra are obtained on a mass spectrometer UltraFlex III TOF/TOF (Bruker Daltonik GmbH, Bremen, Germany) in a linear mode.…”

“…Some compounds of this class exhibit antibacterial properties [7,8]. Additionally, diarylmethane derivatives containing an urea fragment can be used to treat hyperparathyroidism [9][10][11], malaria [12], and atherosclerosis [13] and inhibit lysine-specific demethylase 1 (LSD1) [14], DNA topoisomerase [15], and epoxy hydrolase [16]. e most general approach to these compounds is the acidic media condensation of electron-rich aromatic nucleophiles with aldehydes [17][18][19] or acetals [20][21][22] (Scheme 1(A)).…”

From Regioselective Condensation to Regioselective N‐Alkylation: A Novel and Environmentally Benign Strategy for the Synthesis of N,N′‐Alkyl Aryl Ureas and N,N′‐Dialkyl Ureas

“…1‐Benzyl‐3‐(2,4‐dimethylphenyl)urea ( 3 ma ):33 m.p. 198–199 °C; 1 H NMR (500 MHz, [D 6 ]DMSO): δ =7.65 (s, 1 H, Ar H), 7.63 (br s, 1 H, ArNH), 7.36–7.30 (m, 4 H, Ar H), 7.25 (t, J =6.7 Hz, 1 H, Ar H), 6.93 (s, 1 H, Ar H), 6.90–6.86 (m, 2 H, Ar H, Alkyl NH), 4.29 (d, J =5.6 Hz, 2 H, CH 2 ), 2.20 (s, 3 H, CH 3 ), 2.14 ppm (s, 3 H, CH 3 ); 13 C NMR (125 MHz, [D 6 ]DMSO): δ =155.5, 140.3, 135.5, 130.8, 130.6, 128.3, 127.2, 126.9, 126.7, 126.4, 121.0, 42.8, 20.2, 17.7 ppm.…”

Synthetic Chemistry with an Eye on Future Sustainability

“…Dipropargylamines are important components of biologically active compounds and widely used as synthetic intermediates [111]. However, despite their widespread use, currently reported methods for their synthesis have serious limitations.…”