Medicinal Chemistry Antimalarial drugs 3.pptx

Synthesis of chloroquine
Synthesis of primaquine
Synthesis of quinacrine
Chloroquine is prepared from 2-nitro aniline
Primaquine is prepared from 1,4-dibromopentane
Quinacrine is prepared from 2,4-dichloro benzoic acid

1. Medicinal Chemistry-III A n timal a ria l a g e n ts 3 Department of Pharmacy, Indira Gandhi National Tribal University, Lalpur , Amarkantak (M.P.) Dr. Akhilesh Tiwari Assistant Professor Department of Pharmacy, IGNTU, Amarkantak

2. Contents 2 Synthesis of chloroquine Synthesis of primaquine Synthesis of quinacrine

3. At the end of this lecture, student will be able to Explain the synthetic route for the synthesis of chloriquine Explain the synthetic route for the synthesis of primaquine Explain the synthetic route for the synthesis of quinacrine Learning Objectives 3

4. Synthesis of chloroquine 4 It is prepared by adopting the following four steps viz., ( a ) Preparation of 4, 7-Dichloroquinoline ( i.e., the nucleus) ( b ) P r ep a r a tion o f 2 - amin o-5-di e t h yl amino pe nt ane, diethylamino-4-amino pentane ( i.e., the side chain). o r 1 - ( c ) Condensation of ‘ a ’ and ‘ b ’. ( d ) Addition o f c once n t r at ed pho s phori c a cid t o a ho t e t h anolic solution of the condensed product.

5. A) Prep. of nucleus 5

6. B) Prep. of side chain 6

7. C) Condensation of A and B 7

8. D) Prep. of phosphate salt 8

9. Synthesis of Chloroquine 9

10. Synthesis of Chloroquine Contd… 10

11. Synthesis of Chloroquine Contd… 11

12. Synthesis of Pamaquine 12 Synthesis of the nucleus

13. Synthesis of Pamaquine 13 Condensation of the side chain and nucleus 8 Amino 6 methoxy quiniline 2 chlorodiethyl amino pentane

14. Synthesis of Quinacrine 14 Synthesis of the nucleus Condensation with the side chain

15. Summary 15 Chloroquine is prepared from 2-nitro aniline Primaquine is prepared from 1,4-dibromopentane Quinacrine is prepared from 2,4-dichloro benzoic acid