25634-94-0

Upstream product

• 1914-65-4 tetralin-1-carboxylic acid 
• 201801-48-1 1,2,3,4-tetrahydro-1-(methoxymethylene)naphthalene 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 93340-32-0 3,4-dihydro-1-naphthalenecarboxaldehyde 
• 155566-54-4 1,2,3,4-tetrahydro-1-naphthalenecarbaldehyde 
• 113967-23-0 methyl 1-methyl-1,2,3,4-tetrahydronaphthalene-1-carboxylate 
• 17502-86-2 Methyl 1,2,3,4-tetrahydronaphthalene-1-carboxylate 

Relevant academic research and scientific papers

New Monocyclic, Bicyclic, and Tricyclic Ethynylcyanodienones as Activators of the Keap1/Nrf2/ARE Pathway and Inhibitors of Inducible Nitric Oxide Synthase

A monocyclic compound 3 (3-ethynyl-3-methyl-6-oxocyclohexa-1,4-dienecarbonitrile) is a highly reactive Michael acceptor leading to reversible adducts with nucleophiles, which displays equal or greater potency than the pentacyclic triterpenoid CDDO in inflammation and carcinogenesis related assays. Recently, reversible covalent drugs, which bind with protein targets but not permanently, have been gaining attention because of their unique features. To explore such reversible covalent drugs, we have synthesized monocyclic, bicyclic, and tricyclic compounds containing 3 as an electrophilic fragment and evaluated them as activators of the Keap1/Nrf2/ARE pathway and inhibitors of iNOS. Notably, these compounds maintain the unique features of the chemical reactivity and biological potency of 3. Among them, a monocyclic compound 5 is the most potent in these assays while a tricyclic compound 14 displays a more robust and specific activation profile compared to 5. In conclusion, we demonstrate that 3 is a useful electrophilic fragment for exploring reversible covalent drugs. (Chemical Equation Presented).

Synthesis and biological activity of both enantiomers of kujigamberol isolated from 85-million-years-old Kuji amber

The full-structure of a norlabdane terpenoid, kujigamberol (1) was determined by total synthesis. Key features of the total synthesis are (1) installation of isopentyl group through an o-lithiation of benzamide, (2) construction of tetralone by the RCM reaction, and (3) optical resolution of (±)-1 using chromatographical separation of the corresponding camphanates. X-ray crystallographical analysis of p-bromobenzoate obtained from the more polar camphanate that was identical with a natural derivative, revealed natural kujigamberol to have an S-configuration. Both the natural enantiomer and its (R)-antipode showed the same inhibitory activity toward the mutant yeast and HL-60 cells, while simple analogs without alkyl groups at the C-8 and 9 positions of (±)-1 had no such activity.