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BENZO CONDENSED PYRIDINES: QUINOLINES AND ISOQUINOLINES PowerPoint Presentation
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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

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
slide2

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)

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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”

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Isoquinoline alkaloids

Noskapin

(not analgetic,

not adiction)

Morfinanalogs, binds to opiopeptide (endorfin / enkefalin) reseptors

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Electrophilic Ar. Subst.

Protonation

Halogenation in the Pyridine Ring

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Nucleophilic Addition - Nucleophilic Ar. Subst.

Nu-radicals (Minisci react.)

attacks in the same pos.

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Oxy- and Aminoderivatives - Tautomeri

-All - isomers amino (not imino)

-“One”-Isomers:

Tautomeric Mixt.:

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Synthesis - Quinolines

Synthesis - Isoquinolines