9 aminoacridine


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9 aminoacridine

  1. 1. 9-aminoacridinesAntimalarial drugs
  2. 2. Acridines• Aacridine is formed when an additional benzene ring is fused with pyridine ring of quinoline nucleus. Acridine is overall aromatic, though having nitrogen Pyridine Quinoline Benzene
  3. 3. 9-Amino acridine• has an amino group at C -9• It is a green fluorescent dye• In the past, the compound was used as an antiseptic for treating wounds infections
  4. 4. Structure Activity Relationship• Various types of acridines were synthesized• Acridine has weak antiseptic and antibacterial activity• When a side chain – 2 amino, 5 diethylamino pentane- is introduced at C-9, the compound becomes antimalarial• When methoxy at position 2 and Cl at 6 are introduced –quinacrine- which is antimalarial• Quinacrine was the 1st synthetic agent that was used before quinolines
  5. 5. 9 26 Quinacrine
  6. 6. • When methoxy is shifted to position 6 and Cl to 2 (interchanged)-loss of antimalarial activity• When methoxy is replaced by ethoxy, toxicity is increased• When methoxy is rotated to any other position 1, 3, 4, then 50% activity is lost• When Cl is replaced with other halogens there is successive loss of activity
  7. 7. • Side chain – 2 amino, 5 diethylamino pentane- has no antimalarial activity but when attached to aromatic system the compound became antimalarial• When at position-1, a N is introduced – azacrine- which has good antimalarial activity and rapid onset of action
  8. 8. Azacrine
  9. 9. • A very useful drug was taken from quinacrine by Gemans by separating it into two halves;• 1 half chloroquine active• 2 half was inactive
  10. 10. Chemical synthesis (p-methoxy aniline)2, 4 dichloro benzoic acid Condensation reaction
  11. 11. -HCl2, p-methoxy phenyl amino, 4 chloro benzoic acid
  12. 12. POCl36- chloro , 2-methoxy acredinone
  13. 13. POCl36, 9 dichloro, 2-methoxy acredine
  14. 14. 26 chloro, 9 diethylaminopentyl, 2-methoxy, acredine
  15. 15. Therapeutic uses• Treating erythrocytic stage of malaria• Earlier, was used in treating black water fever• Have anthalmentic activity against intestinal parasites• It is eliminated slowly and have side effects
  16. 16. Non-therapeutic use• Being green fluorescent dye, used to visualize blood cells, particularly platelets• Platelets store the dye in dense granules
  17. 17. Side effects• Gastric irritation• Staining of tongue and skin
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