A novel acetylenic tricyclic bis-(cyano enone), TBE-31, is a lead compound in a series of tricyclic compounds with enone functionalities in rings A and C. Nanomolar concentrations of this potent multifunctional molecule suppress the induction of the inflammatory protein, inducible nitric oxide synthase, activate phase 2 cytoprotective enzymes in vitro and in vivo, block cell proliferation, and ...

CCG-1423 and related analogues represent a new class of inhibitors of Rho/MKL1/SRF-mediated gene transcription, a pathway that has been implicated in both cancer and fibrosis. The molecular target for these compounds is unknown. To facilitate its identification, a series of tag-free photoaffinity probes was designed and synthesized, each one containing a photoactivatable group and an acetylenic...

During a screening program for new agrochemicals from Chinese medicinal herbs, the ethanol extract of Notopterygium incisum rhizomes was found to possess strong nematicidal activity against the two species of nematodes, Bursaphelenchus xylophilus and Meloidogyne incognita. Based on bioactivity-guided fractionation, the four constituents were isolated from the ethanol extract and identified as c...

Structure-activity relation studies have established that the alkyl side chain in tetrahydrocannabinol (THC) plays a crucial role in the activation of the cannabinoid receptor. Unfortunately, the flexible nature of this side chain has hampered efforts to elucidate the precise nature of the interaction of THC with its receptors. Therefore, a series of analogs with structurally restrained side ch...

Background: Enzymatic kinetic resolution is proved as an efficient strategy of accessing chiral secondary alcohols in organic synthesis. Although several synthetic methods have been developed for the preparation of chiral acetylenic alcohol, biotransformation remains as a direct approach in the synthesis of polyacetylene lipids, which represent an intriguing class of marine natural products fea...

Photochemically, covalent cycloaddition products of flavoquinone and acetylenic enzyme inhibitors have been prepared and elucidated, which appear analogous to flavoprotein-inhibitor complexes (monoamine and lactate oxidase). The additions occur with inhibitors of general type H C = C — C H < at the C (4a )=N(5 ) azomethine grouping of oxidized flavin. The spectral properties of adducts and thei...

Propargyl-linked antifolates that target dihydrofolate reductase are potent inhibitors of several species of pathogenic bacteria and fungi. This novel class of antifolates possesses a relatively uncommon acetylenic linker designed to span a narrow passage in the enzyme active site and join two larger functional domains. Because the use of alkyne functionality in drug molecules is limited, it wa...

The importance of cyclopentanoid natural products continues to inspire the development of methods for the synthesis of 5-membered rings. For example, the Conia–ene reaction provides an atomeconomical synthesis of methylenecyclopentanes by the thermal cyclization of e-acetylenic carbonyl compounds. While the classic thermal reaction is limited to the exocyclic cyclization mode, group 6 metal com...

Acetylenic sulfones attached to solid supports by means of ester linkers were employed in a variety of cyclization and cycloaddition reactions, followed by cleavage of the products from the resin by ester hydrolysis or reductive desulfonylation.