21857-41-0Relevant articles and documents
Total Synthesis of 4,5-Didehydroguadiscine: A Potent Melanogenesis Inhibitor from the Brazilian Medicinal Herb, Hornschuchia obliqua
Tanabe, Genzoh,Sugano, Youta,Shirato, Miki,Sonoda, Naoki,Tsutsui, Nozomi,Morikawa, Toshio,Ninomiya, Kiyofumi,Yoshikawa, Masayuki,Muraoka, Osamu
, p. 1536 - 1542 (2015/08/03)
The first total synthesis of the 7,7-dimethylaporphinoid, 4,5-didehydroguadiscine (6), originally isolated from the stems and roots of Hornschuchia oblique (Annonaceae), was achieved by the condensation of homopiperonylamine (7) with an α,α-dimethylphenylacetic acid derivative (8) and subsequent Pschorr reaction of the resulting benzylisoquinoline intermediate (22). The reported 13C NMR data were partially revised on the basis of the analysis of HMBC spectra measured under different conditions. The melanogenesis inhibitory activity (IC50 = 4.7 μM) of 6 was 40 times stronger than that of arbutin (174 μM), which was used as reference standard. Furthermore, 6 was the most potent natural melanogenesis inhibitor within this class of compounds. (Chemical Equation Presented).
A direct synthesis of 2-arylpropenoic acid esters having nitro groups in the aromatic ring: A short synthesis of (±)-coerulescine and (±)-horsfiline
Selvakumar,Azhagan, A.Malar,Srinivas,Krishna, G.Gopi
, p. 9175 - 9178 (2007/10/03)
A short synthesis of 2-arylpropenoic acid esters that possess nitro groups in their phenyl ring using common and less expensive reagents is described. The usefulness of this methodology is substantiated by the efficient total syntheses of (±)-coerulescine and (±)-horsfiline from the 2-arylpropenoic acid esters obtained.
