A series of quinolinyl and isoquinolinyl phenyl ketones was synthesized and their CB(2) receptor-dependent G-protein activities were determined using the [(35)S]GTPgammaS binding assay. Both quinoline and isoquinoline derivatives exhibited similar CB(2) receptor agonist activity, the most potent ligands being the 2-(Me(2)N)-phenyl substituted derivatives, which were also full agonists at the CB(2)-receptor.
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http://dx.doi.org/10.1016/j.bmc.2009.05.013 | DOI Listing |
J Org Chem
March 2023
School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 205 Luoshi Road, Wuhan, 430070, P. R. China.
A [3 + 2] cycloaddition reaction of -aminopyridines, -aminoquinolines, and -aminoisoquinolines with 1-bromoethene-1-sulfonyl fluoride (BESF) was performed to obtain optimum yields of various useful pyrazolo[1,5-]pyridinyl, pyrazolo[1,5-]quinolinyl, and pyrazolo[5,1-]isoquinolinyl sulfonyl fluorides (43-90% yield). The transformation process showed broad substrate specificity, mild reaction conditions, and operational simplicity. Therefore, the reaction has great applicable value in the field of medicinal chemistry and other disciplines.
View Article and Find Full Text PDFChemistry
September 2021
Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas, 77842-3012, USA.
Reactions of Li [(η -C H )Re(NO)(PPh )] with 2- and 4-chloroquinoline or 1-chloroisoquinoline give the corresponding σ quinolinyl and isoquinolinyl complexes 3, 6, and 8. With 3 and 8 there is further protonation to yield HCl adducts, but additions of KH give the free bases. Treatment of 3 with HBF ⋅OEt or H(OEt ) BAr gives the quinolinium salts [(η -C H )Re(NO)(PPh )(C(NH)C(CH) C(CH)(CH))] X (3-H X ; X =BF /BAr , 94-98 %).
View Article and Find Full Text PDFJ Agric Food Chem
January 2021
College of Plant Protection, Northwest A&F University, 3 Taicheng Road, Yangling, 712100 Shaanxi, China.
Fungal infections could cause tremendous decreases in crop yield and quality. Natural products, including flavonoids and (iso)quinolines, have always been an important source for lead discovery in medicinal and agricultural chemistry. To promote the discovery and development of new fungicides, a series of 3-(iso)quinolinyl-4-chromenone derivatives was designed and synthesized by the active substructure splicing principle and evaluated for their antifungal activities.
View Article and Find Full Text PDFOrg Lett
December 2019
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering , Shaanxi Normal University, No.620 West Chang'an Avenue , Xi'an 710119 , China.
A general approach for the synthesis of 3-(iso)quinolinyl 4-chromenones and 3-(iso)quinolinyl 4-quinolones from (iso)quinoline -oxides and ynones under metal-free conditions was developed. The reaction of (iso)quinoline -oxide with the electron-deficient alkyne first generated an (iso)quinolinyl β-diketone intermediate, which then underwent an intramolecular dehydration, affording 3-(iso)quinolinyl 4-chromenones and 3-(iso)quinolinyl 4-quinolones.
View Article and Find Full Text PDFJ Am Chem Soc
January 2018
Department of Chemistry, University of California, Berkeley, California 94720, United States.
We report stereodivergent allylic substitution reactions of allylic esters with prochiral enolates derived from azaaryl acetamides and acetates to form products from addition of the enolates at the most substituted carbon of an allyl moiety with two catalysts, a chiral metallacyclic iridium complex and a chiral bisphosphine-ligated copper(I) complex, which individually control the configuration of the electrophilic and nucleophilic carbon atoms, respectively. By simple permutations of enantiomers of the two catalysts, all four stereoisomers of products containing two stereogenic centers were synthesized individually with high diastereoselectivity and enantioselectivity. A variety of azaaryl acetamides and acetates bearing pyridyl, benzothiazolyl, benzoxazolyl, pyrazinyl, quinolinyl and isoquinolinyl moieties were all found to be suitable for this transformation.
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