Synthesis of Aza-brazilin/diarylindan-Based Hybrid

Abstract

Natural products play the most important role in the development of drugs. The design and synthesis of natural products hybrids seem to be a promising approach to increase the number and the diversity of compounds for pharmacological testing and were expected to disclose an avenue toward the development of valuable leads for medicinal applications. In this paper the synthesis of an aza-brazilin/1,3-diarylindan-based hybrid starting from 1,2-dimethoxy-benzene was reported. The synthesis finished in 9 steps including Friedel-Crafts acylation, Claisen condensation, Knoevenagel condensation, Nazarov cyclization, aminolysis of β-keto esters, α-hydroxylation of β-dicarbonyl compounds, reduction of ketone, amide and the intra-molecular Friedel-Crafts cyclization reaction.

Transport and Metabolism Behavior of Brazilein during Its Entrance into Neural Cells

“…Previous researchers have extensively studied the mechanism of COMT methylation process from structural perspective [30] and functional perspective [34] . Docking model in this research displayed the combination between brazilein and COMT complex with SAM and Mg 2+ (PDB code: 1H1D), which was corresponding to the proposed catalytic mechanism [27] , [35] . From molecular level, brazilein bond to the enzyme active site which is near the surface of the enzyme and was close to the methyl donator SAM and cofactor Mg 2+ .…”

“…10-O-methylbrazilein, as a single-substituted derivative, was not reported in the previous studies. Research groups rarely reported single-substituted derivatives of brazilein by chemical reaction [27] , [28] . Thus, the chemical properties and biological activities of this new analogue were yet unknown.…”