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LESSON 17.

CHEMISTRY OF BIOLOGICALLY ACTIVE

HETEROFUNCTIONAL AND HETEROCYCLIC LOW-MOLECULAR

ORGANIC SUBSTANCES

Required base level.

Physical and chemical properties of amines. The concept of heterofunctional

compounds and heterocyclic compounds.

Questions for the preparation for the lesson.

1. Dibasic carboxylic acids: oxalic, malonic, succinic, glutaric, fumaric.

Formation of cyclic anhydrides and amides.

2. Aminoalcohols: colamine, choline, acetylcholine, noradrenaline, adrenaline.

3. Reaction of cyclization of α- and γ-hydroxy acids and α- and γ-amino

acids, hydrolysis of lactones and lactams.

4. Reactions of elimination of β-hydroxy- and β-amino acids.

5. Ketoacids: pyruvic, acetoacetic, oxaloacetic. Keto-enol tautomerism.

7. Heterofunctional derivatives of benzene. Medicines based on p‑amino-

phenol, p‑aminobenzoic, sulfanilic and salicylic acids.

8. Heterocycles: pyrrole, pyridine, pyrimidine, imidazole, indole, purine.

Aromaticity of heterocycles.

Test-control on the topic “chemistry of biologically active heterofunctional

and heterocyclic low-molecular organic substances”.

Homework exercises.

1. Draw the structure of biogenic amines – kolamin, choline, norepinephrine,

adrenaline.

2. Write down the equations for the specific reactions that occur during

heating:

a) α-hydroxyacetic and α-aminoacetic acids; b) β-hydroxybutyric and

β-aminobutyric acids; d) γ-hydroxyvaleric and γ-aminovaleric acids.

3. Write schemes for the hydrolysis of γ-butyrolactone and γ-butyrolactam.

4. Write the equation for the decarboxylation of acetoacetic acid. What

substances are included in the «ketone bodies»? Write two tautomeric forms of

acetoacetic acid.

5. Write the equations of reactions for the preparation of medicinal

compounds that are derived:

a) salicylic acid: (sodium salicylate, methyl salicylate, phenyl salicylate,

acetylsalicylic acid). How is the quality of aspirin tested?