Historical Background:
The first tetracycline, chlortetracycline, was discovered in the late 1940s in a soil sample.
Nomenclature:
Tetracyclines are named for the presence of four ("tetra-") hydrocarbon rings in their structure.
Stereochemistry:
The tetracycline core structure has several chiral centers. Differences in these centers result in different tetracycline antibiotics.
Structure-Activity Relationship:
These are broad-spectrum antibiotics, named for their four-ring structure, that also work by inhibiting bacterial protein synthesis.
Their key structural elements include:
1.Four-Ring Structure:
The four-ring structure is important for the function of tetracyclines.
Changes to this structure can greatly affect their activity.
2.Functional Groups:
The functional groups attached to the tetracycline core are crucial for their antibacterial activity.
For example, the hydroxyl and dimethylamino groups at positions C-5 and C-4', respectively, are important for antibacterial activity, and modifications at these positions can result in decreased activity.
Chemical Degradation:
Tetracyclines can be degraded by epimerization and loss of the dimethylamino group