Synthesis of novel analogs of diptoindonesin G, compounds formed thereby, and pharmaceutical compositions containing them
Disclosed are unnatural analogs of Diptoindonesin G, methods to make the analogs, pharmaceutical compositions containing the analogs, and methods of using the analogs to inhibit neoplastic cell growth.
1. A compound selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of —H, —OH, —OR 10 , —NH 2 , —NHR 10 , and —NR 10 R 11 , wherein R 10 and R 11 are independently selected from the group consisting of C 1 -C 6 -alkyl, provided that R 1 , R 2 , and R 4 are not simultaneously —OH or —OR 10 ; and further provided that at least one of R 6 , R 7 , or R 8 is —OH;
R 9 is —O—, —NH—, or —S—; and
salts thereof.
2. The compound of claim 1 , wherein the salts are pharmaceutically suitable salts.
3. A compound selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of —H, —OH, —OR 10 , —NH 2 , —NHR 10 , and —NR 10 R 11 , wherein R 10 and R 11 are independently selected from the group consisting of C 1 -C 6 -alkyl, provided that R 1 , R 2 , and R 4 are not simultaneously —OH or —OR 10 , and further provided that at least one of R 1 , R 3 , R 4 , or R 5 is —OH, and at least one of R 6 , R 7 , or R 8 is —OH; and
wherein R 9 is —O—; and
salts thereof.
4. The compound of claim 3 , wherein R 1 is —OH.
5. The compound of claim 3 , wherein R 2 is —OH.
6. The compound of claim 3 , wherein R 3 is —OH.
7. The compound of claim 3 , wherein R 4 is —OH.
8. The compound of claim 3 , wherein R 5 is —OH.
9. The compound of claim 3 , wherein R 6 is —OH.
10. The compound of claim 3 , wherein R 7 is —OH.
11. The compound of claim 3 , wherein R 8 is —OH.
12. A compound selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of —H, —OH, —OR 10 , —NH 2 , —NHR 10 , and —NR 10 R 11 , provided that at least one of R 1 , R 2 , R 3 , R 4 , R 5 is —OH, and at least one of R 6 , R 7 , and R 8 is —OH, wherein R 10 and R 11 are independently selected from the group consisting of C 1 -C 6 -alkyl, and provided that R 1 , R 2 , R 4 , and R 6 are not simultaneously —OH;
wherein R 9 is —NH—; and
salts thereof.
13. The compound of claim 12 , wherein R 1 is —OH.
14. The compound of claim 12 , wherein R 2 is —OH.
15. The compound of claim 12 , wherein R 3 is —OH.
16. The compound of claim 12 , wherein R 4 is —OH.
17. The compound of claim 12 , wherein R 5 is —OH.
18. The compound of claim 12 , wherein R 6 is —OH.
19. The compound of claim 12 , wherein R 7 is —OH.
20. The compound of claim 12 , wherein R 8 is —OH.
21. A compound selected from the group consisting of:
wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are independently selected from the group consisting of —H, —OH, —OR 10 , —NH 2 , —NHR 10 , and —NR 10 R 11 , wherein R 10 and R 11 are independently selected from the group consisting of C 1 -C 6 -alkyl, provided that R 1 , R 2 , R 4 , and R 6 are not simultaneously —OH; and
wherein R 9 is —S—; and
salts thereof.
22. The compound of claim 21 , wherein R 1 is —OH.
23. The compound of claim 21 , wherein R 2 is —OH.
24. The compound of claim 21 , wherein R 3 is —OH.
25. The compound of claim 21 , wherein R 4 is —OH.
26. The compound of claim 21 , wherein R 5 is —OH.
27. The compound of claim 21 , wherein R 6 is —OH.
28. The compound of claim 21 , wherein R 7 is —OH.
29. The compound of claim 21 , wherein R 8 is —OH.
30. A pharmaceutical composition comprising a compound as recited in claim 1 , in combination with a pharmaceutically suitable delivery vehicle.
31. A method of inhibiting neoplastic cell growth, the method comprising contacting a neoplastic cell or a cell suspected of being neoplastic with a growth inhibiting-effective amount of a compound as in claim 1 .