Compounds with activity at serotonin (5-hydroxytryptamine) 5-HT and α adrenergic receptors have potential for the treatment of central nervous system disorders, drug addiction or overdose. Isolaureline, dicentrine and glaucine enantiomers were synthesized, and their in vitro functional activities at human 5-HT and adrenergic α receptor subtypes were evaluated. The enantiomers of isolaureline and dicentrine acted as antagonists at 5-HT and α receptors with (R)-isolaureline showing the greatest potency (pK = 8.14 at the 5-HT receptor). Both (R)- and (S)-glaucine also antagonized α receptors, but they behaved very differently to the other compounds at 5-HT receptors: (S)-glaucine acted as a partial agonist at all three 5-HT receptor subtypes, whereas (R)-glaucine appeared to act as a positive allosteric modulator at the 5-HT receptor.

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This chapter describes the biosynthesis and biomimetic synthesis of naturally occurring flavonoid Diels-Alder adducts found either from the family Moraceae or Zingiberaceae. The main topics addressed are biosynthetic studies by employing Morus alba L. cell cultures through feeding experiments of various exogenous substrates and putative precursors, as well as a various biomimetic approach for the chemical syntheses of flavonoid Diels-Alder natural products.

A series of C4-substituted tertiary nitrogen-bearing 2 0-hydroxychalcones were designed and synthesised based on a previous mixed type acetylcholinesterase inhibitor. Majority of the 2 0-hydroxychalcone analogues displayed a better inhibition against acetylcholinesterase (AChE) than butyrylcholinesterase (BuChE). Among them, compound 4c was identified as the most potent AChE inhibitor (IC 50 : 3.3 mM) and showed the highest selectivity for AChE over BuChE (ratio >30:1). Molecular docking studies suggested that compound 4c interacts with both the peripheral anionic site (PAS) and catalytic anionic site (CAS) regions of AChE. ADMET analysis confirmed the therapeutic potential of compound 4c based on its blood-brain barrier penetrating. Overall, the results suggest that this 2 0-hydroxychalcone deserves further investigation into the therapeutic lead for Alzheimer's disease (AD).

The asymmetric unit of the title compound, [Cu2(C16H31O2)4(C10H8N2)2]·2CH3OH, contains one half-mol­ecule of the metal complex solvated by a methanol mol­ecule. In the complex, two of the metal atoms are doubly bridged by two monodentate bridging hexa­deca­noate ligands around a center of inversion. The square-pyramidal geometry around each CuII ion is completed by a terminal hexa­deca­noate O atom and two N atoms from a 2,2′-bipyridine ligand. The alkyl chains of the carboxyl­ate ligands are arranged in a parallel manner with an all-trans conformation. In the crystal, a π–π inter­action formed by the bipyridine rings [centroid–centroid separation = 3.7723 (17) Å] and inter­molecular C—H⋯O hydrogen bonds link the complex mol­ecules into infinite chains along the b axis. An O—H⋯O interaction between the methanol solvate and one of the carboxylate O atoms is also observed.