A novel Diels-Alder (DA) reaction with 4-nitro-1(2H)-isoquinolones acting as the dienophile afforded 5(6H)-phenanthridone derivatives. The DA reaction of 4-nitro-1(2H)-isoquinolone with 1-methoxy-1,3-butadiene gave biologically active 5(6H)-phenanthridone possessing in a high yield. Regioselectivity of 4-nitro-1(2H)-isoquinolones with 1-methoxy-3-silyloxy-1,3-butadiene was calculated using molecular orbital (MO) calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1248/cpb.54.209 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Total Syntheses of Diepoxy-Kaurane Diterpenoids Enabled by a Bridgehead-Enone-Initiated Intramolecular Cycloaddition.
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Here, we report the enantioselective total syntheses of four diepoxy--kaurane diterpenoids including (-)-Macrocalin B, (-)-Acetyl-macrocalin B, and (-)-Isoadenolin A and the revised structure of (-)-Phyllostacin I, which hinges on the strategic design of a regioselective and stereospecific trapping of a highly reactive [3.2.1]-bridgehead enone intermediate via a tethered intramolecular Diels-Alder reaction.
View Article and Find Full Text PDFOrvinol-based opioid receptor antagonist fluorinated at C(20)-pharmacophore.
Eur J Med Chem
December 2024
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, bld. 1, Moscow, 119334, Russia. Electronic address:
Thevinols and their 3-O-demethylated relatives, orvinols, are derivatives of the Diels-Alder adduct of natural alkaloid thebaine with methyl vinyl ketone. Taken together, thevinols and orvinols constitute an important family of opioid receptor (OR) ligands playing an important role in both the OR mediated antinociception and OR antagonism. Herein, we disclose for the first time the antagonist activity of the N-allyl substituted orvinol derivative fluorinated within the pharmacophore associated with C(20) and its surrounding.
View Article and Find Full Text PDFMechanochemical Release of 9,10-Diphenylanthracene via Flex-Activation of Its 1,4-Diels-Alder Adduct.
ACS Macro Lett
December 2024
School of Materials Science and Engineering, Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Sun Yat-Sen University, Guangzhou 510006, China.
Flex-activated mechanophores capable of releasing small molecules utilize bond bending to facilitate their mechanochemical activation without compromising the overall macromolecular architecture, which have great potential in various applications. However, the development of such mechanophores remains underexplored. Here we report a novel flex-activated mechanophore based on the 1,4-Diels-Alder (DA) adduct of 9,10-diphenylanthracene (DPA) with acetylenedicarboxylate (ADC).
View Article and Find Full Text PDFA Catch-Release Strategy for the Genomics-Driven Discovery of Antiproliferative Furan-Functionalized Peptides.
Angew Chem Int Ed Engl
December 2024
Leibniz Institute for Natural Product Research and Infection Biology, HKI, Department of Biomolecular Chemistry, Beutenbergstr. 11a, 07745, Jena, GERMANY.
Furan-functionalized peptides are of significant pharmacological interest due to their pronounced bioactivities and unique potential for orthogonal bioconjugation and derivatization. However, naturally occurring peptides with furyl side chains are exceedingly rare. This study presents a streamlined method to predict and assess the microbial production of peptides incorporating 3-furylalanine (Fua) moieties.
View Article and Find Full Text PDFEnantioselective Synthesis of Atropisomeric Tri-Axis Naphthalenes via Diels-Alder Reaction and Dehydrative Aromatization of Isobenzofurans.
Angew Chem Int Ed Engl
December 2024
Department of Chemistry, Fudan University, 220 Handan Rd., Shanghai, 200433, China.
Atropisomers with multiple stereogenic axes have attracted much attention due to their increasing significance in the fields of natural products, chiral materials, and drug discoveries. However, the catalytic stereoselective construction of axially chiral ring scaffolds with more than two axes on a single benzene ring remains a challenging task. Herein, we present an efficient method for synthesizing triaxially chiral polysubstituted naphthalene scaffolds via sequential Ni(II)-catalyzed Diels-Alder reaction of isobenzofurans and TfOH-promoted dehydrative aromatization reaction.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!