Prezentace aplikace PowerPoint

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HETEROCYCLES
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HETEROCYCLES

• organic compounds, containing other atoms than
  carbon, bend in cycle
• different atom is called heteroatom
• most frequent heteroatoms
• Oxygen
• Sulphur
• Nitrogen

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Classification
Oxygen containing
Sulphur containing
1.
Nitrogen contaning
combined
saturated
cont. nonconjugated double bonds
2.
unsaturated
cont. conjugoated double bonds
3.
According to number of atoms in cycle
3,4,5,6,7,8 and more atoms rings
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5atom heterocycles cont. oxygen
O

• furan
• liquid, not solved in water

Complete reduction

• tetrahydrofuran (oxolan)
• excellent solvent, miscible with water, solve
  many organic compounds
• this ring is base of furanose forms of
  sacharides
• 2- furancarbaldehyde - produced after exposure
  of aldopentose to strong mineral acids, colored
  reactions with phenols

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5atom heterocycles cont. sulphur
Complete reduction

• thiophane (thiolan)
• part of structure of biotine (carboxylations)

• thiophene
• similar to benzene
• in coal tar

Complete reduction

• thiazolidin
• part of structure of peniciline

• thiazol
• part of structure of vit B1
• part of structure of sulphonamide sulfathiazolu

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5atom heterocycles cont. nitrogen

• pyrrole
• in coal tar
• tetrapyrroles 4 pyrrole rings connected by
  methine bridges, hemoglobin, chlorophyl, bile
  dyes, vit. B 12

reduction

• 2-pyrroline

reduction

• pyrrolidine
• proline
• hydroxyproline

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5atom heterocycles cont. nitrogen

• pyrazole
• 1,2-diazol
• part of antipyretics (phenazone, aminophenazone
  relatively high toxicity)

úplná redukce

• pyrazolidine
• part of antirevmatisc (phenylbutazone,
  ketophenylbutazone )

• imidazole
• 1,3-diazol
• part of histidine (bazic aminoacid, part of
  histones) and histamine (alergic reactions)
• part of structure of biotine (vit.H)

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6atom heterocycles cont. oxygen
4H-pyran
2H-pyran
Comlete reduction

• tetrahydropyran
• part of pyranose forms of sacharides

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6atom heterocycles cont. nitrogen

• pyridine
• in coal tar
• toxic
• solvent
• part of nicotin acid and alkaloid nicotine
• part of vit. B6 (pyridoxin)

N
Complete reduction

• piperidine
• part of structure of Dolsine

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6atom heterocycles cont. nitrogen diazines
pyridazine 1,2-diazine

• pyrimidine
• 1,3-diazine
• part of pyrimidine bases
• cytosine
• uracil
• thymine
• part of vit. B1 (aneurin)
• part of barbiturates

pyrazine 1,4-diazine
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Pyrimidine bases
(RNA)
(DNA)
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Nitrogen cont. heterocycles with condensed rings

• chinoline
• basic structure of chinoline alkaloids, fe.
  chinine (antimalarikum and antipyretikum)

• isochinoline
• basic structure of isochinoline alkaloids
• papaverine (suppresses cramps of smooth
  muscles)
• morphine, codeine (analgetikum, antitussikum)
• curare alkaloids

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Nitrogen cont. heterocycles with condensed rings

• indole produced by bacterial decomposition of
  AA tryptophane in stool, part of structure
• blue dye indigo
• indole alkaloids
• strychnine
• ergot alkaloids (LSD, ergotamine, ergometrine)

• purine
• part of purine bases
• adenine
• guanine
• part of uric acid
• part of methylxantines
• caffeine
• theophyline, theobromine

14
Purine bases
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Nitrogen cont. heterocycles with condensed rings

• pteridine
• most important derivates folic acids (transfer
  of 1C fragments)

• benzopteridine
• its dioxoderivate isoalloxazine is basic
  structure of riboflavin, vitamine B2