Synthesis of the antibacterial benzoquinone primin and its water-soluble analogue, primin acid

Synthesis

Volumn , Issue 7, 2010, Pages 1141-1144

  Bhattacharya, Asish K ^a   Kaur, Tanpreet ^a   Ganesh, Krishna N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

1,4 benzoquinones; Antibacterial; Johnson Claisen rearrangement; Primin; Primin acid

Indexed keywords

ANTIBACTERIAL; BENZOQUINONES; GRIGNARD REACTION; JOHNSON-CLAISEN REARRANGEMENTS; NATURAL PRODUCTS;

ETHERS; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

ACIDS;

(2 METHOXY 6 PENTYL 1,4 BENZOQUINONE); 5 (5 METHOXY 3,6 DIOXOCYCLOHEXA 1,4 DIEN 1 YL)PENTANOIC ACID; BENZOQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; DRUG SYNTHESIS; GRIGNARD REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77949826071     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218666     Document Type: Article

References (28)

1. Gunatilaka A A. L., Berger J M., Evans R, Miller J S., Wisse J H., Neddermann K M., Bursuker I, Kingston D G. I., J. Nat. Prod. 2001 64 2
2. Schildknecht H, Schmidt H, Z. Naturforsch., B 1967 22b 287
3. Bloch B, Karrer P, Vjschr. Naturforsch. Ges. 1927 72 1
4. Chem. Abstr. 1928, 22: 2784
5. Marini-Bettolo G B., Monache F D., daLima O G., Coelho S B., Gazz. Chim. Ital. 1971 101 41
6. Bernays E, Lupi A, Bettolo R M., Mastrofrancesco C, Tagliatesta P, Experientia 1984 40 1010
7. Pongcharoen W, Rukachaisirikul V, Phongpaichit S, Sakayaroj J, Chem. Pharm. Bull. 2007 55 1404
8. Tasdemir D, Brun R, Yardley V, Franzblau S G., Redi P, Chem. Biodivers. 2006 3 1230; and references cited therein
9. Carlsen B C., Menné T, Johansen J D., Contact Dermatitis 2008 59 96
10. Bonamonte D, Filotico R, Mastrandrea V, Foti C, Angelini G, Contact Dermatitis 2008 59 174
11. Fortina A B., Piaserico S, Larese F, Recchia G P., Corradin M T., Gennaro F, Carrabba E, Peserico A, Contact Dermatitis 2001 44 283
12. Bieber L W., Chiappeta A D. A., Souza M A. D. M., Generino M, Neto P R., J. Nat. Prod. 1990 53 706
13. Mabic S, Vaysse L, Benezra C, Lepoittevin J.-P, Synthesis 1999 1127
14. Davis C J., Hurst T E., Jacob A M., Moody C J., J. Org. Chem. 2005 70 4414
15. Jacob A M., Moody C J., Tetrahedron Lett. 2005 46 8823
16. Bhattacharya A K., Sharma R P., Heterocycles 1999 51 1681
17. Bhattacharya A K., Jain D C., Sharma R P., Roy R, McPhail A T., Tetrahedron 1997 53 14975
18. Bhattacharya A K., Pal M, Jain D C., Joshi B S., Roy R, Rychlewska U, Sharma R P., Tetrahedron 2003 59 2871
19. Bhattacharya A K., Pathak A K., Sharma R P., Mendeleev Commun. 2007 17 27
20. Bhattacharya A K., Kaur T, Synlett 2007 745; and references cited therein
21. Bhattacharya A K., Rana K C., Mujahid M, Sehar I, Saxena A K., Bioorg. Med. Chem. Lett. 2009 19 5590
22. Bhattacharya A. K., Kaur T. unpublished results.
23. Johnson W S., Werthemann L, Bartlett W R., Brocksom T J., Li T.-T, Faulkner D J., Petersen M R., J. Am. Chem. Soc. 1970 92 741
24. Ziegler F E., Chem. Rev. 1988 88 1423
25. Meza-Avina M E., Ordonez M, Fernandez-Zertuche M, Rodriguez-Fragoso L, Reyes-Esparza J, delosRios-Corsino A A. M., Bioorg. Med. Chem. 2005 13 6521
26. Corey E J., Venkateswarlu A, J. Am. Chem. Soc. 1972 94 6190
27. Lauchli R, Shea K J., Org. Lett. 2006 8 5287
28. Ankala S V., Fenteany G, Tetrahedron Lett. 2002 43 4729