BENZO CONDENSED PYRIDINES: QUINOLINES AND ISOQUINOLINES Alkaloid Natural Products Largets class of secondary metabolites, >6500 compds known Contains N,

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Presentation transcript:

BENZO CONDENSED PYRIDINES: QUINOLINES AND ISOQUINOLINES Alkaloid Natural Products Largets class of secondary metabolites, >6500 compds known Contains N, most compds basic (alkaline), often heterocyclic Often highly toxic Found in certain higher plants (seldom in bacteria) Little is known regarding why alkaloids are produced Biosynthesis from amino acids

Quinoline alkaloids Cinchona pubescens (Kinatre) from South America R=OMe: Quinine (Cinchonidine epimer at C-9) R=H: Quinidine (Cinchonine epimer at C-9) Quinidine: Antiarytmic Quinine: Antimalaria Dihydroquini(di)ne and der. Chiral ligands Asym. dihydroxylation (Sharpless)

Isoquinoline alkaloids Curare - Pilgift - Søramerikanske indianere Bland. Av flere alkaloider med muskeslammende effekt Flere plantekilder bl.a. Chondodendron tomentosum Ex. Mivacurium klorid Muscle relax, anesthesia Suksametonium, Curacit® “Nesset”

Isoquinoline alkaloids Morfinanalogs, binds to opiopeptide (endorfin / enkefalin) reseptors Noskapin (not analgetic, not adiction)

Protonation Electrophilic Ar. Subst. Halogenation in the Pyridine Ring

Nucleophilic Addition - Nucleophilic Ar. Subst. Nu-radicals (Minisci react.) attacks in the same pos.

ANRORC (Add. Of Nu., Ring Opening and Ring Closure)

Oxy- and Aminoderivatives - Tautomeri -All - isomers amino (not imino) -“One”-Isomers: Tautomeric Mixt.:

Synthesis - Quinolines Synthesis - Isoquinolines