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BENZO CONDENSED PYRIDINES: QUINOLINES AND ISOQUINOLINES

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)

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BENZO CONDENSED PYRIDINES: QUINOLINES AND ISOQUINOLINES

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  1. 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

  2. Cinchona pubescens (Kinatre) from South America Quinoline alkaloids 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)

  3. 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”

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

  5. Electrophilic Ar. Subst. Protonation Halogenation in the Pyridine Ring

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

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

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

  9. Synthesis - Quinolines Synthesis - Isoquinolines

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