The synthesis and antimicrobial activity of heterocyclic derivatives of totarol

ACS Medicinal Chemistry Letters

Volumn 3, Issue 10, 2012, Pages 818-822

  Kim, Michelle B ^a   O'Brien, Terrence E ^a   Moore, Jared T ^a   Anderson, David E ^a   Foss, Marie H ^b   Weibel, Douglas B ^b,c   Ames, James B ^a   Shaw, Jared T ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c University of Wisconsin Madison   (United States)

Author keywords

antimicrobial activity; FtsZ; small molecule inhibitors; structure activity relationships and optimization; totarol

Indexed keywords

ANTIINFECTIVE AGENT; FTSZ PROTEIN; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; TOTAROL; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL CELL; CELL DIVISION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 84867342820     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3001775     Document Type: Article

References (33)

1. Tan, C. M.; Therien, A. G.; Lu, J.; Lee, S. H.; Caron, A.; Gill, C. J.; Lebeau-Jacob, C.; Benton-Perdomo, L.; Monteiro, J. M.; Pereira, P. M.; Elsen, N. L.; Wu, J.; Deschamps, K.; Petcu, M.; Wong, S.; Daigneault, E.; Kramer, S.; Liang, L.; Maxwell, E.; Claveau, D.; Vaillancourt, J.; Skorey, K.; Tam, J.; Wang, H.; Meredith, T. C.; Sillaots, S.; Wang-Jarantow, L.; Ramtohul, Y.; Langlois, E.; Landry, F.; Reid, J. C.; Parthasarathy, G.; Sharma, S.; Baryshnikova, A.; Lumb, K. J.; Pinho, M. G.; Soisson, S. M.; Roemer, T. Restoring Methicillin-Resistant Staphylococcus aureus Susceptibility to beta-Lactam Antibiotics Sci. Transl. Med. 2012, 4, 126ra35
2. Bendall, J. G.; Cambie, R. C. Totarol: A non-conventional diterpenoid Aust. J. Chem. 1995, 48, 883-917
3. Clarkson, C.; Campbell, W. E.; Smith, P. In vitro antiplasmodial activity of abietane and totarane diterpenes isolated from Harpagophytum procumbens (Devil's Claw) Planta Med. 2003, 69, 720-724
4. Yamaji, K.; Mori, S.; Akiyama, M.; Kato, A.; Nakashima, T. The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces J. Chem. Ecol. 2007, 33, 2254-2265
5. Muroi, H.; Kubo, I. Antibacterial activity of anacardic acid and toatarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus J. Appl. Bacteriol. 1996, 80, 387-394
6. Kubo, I.; Muroi, H.; Himejima, M. Antibacterial activity of totarol and its potentiation J. Nat. Prod. 1992, 55, 1436-40
7. Nicolson, K.; Evans, G.; O'Toole, P. W. Potentiation of methicillin activity against methicillin-resistant Staphylococcus aureus by diterpenes FEMS Microbiol. Lett. 1999, 179, 233-239
8. Haraguchi, H.; Oike, S.; Muroi, H.; Kubo, I. Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi Planta Med. 1996, 62, 122-125
9. Micol, V.; Mateo, C. R.; Shapiro, S.; Aranda, F. J.; Villalain, J. Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes Biochim. Biophys. Acta, Biomembr. 2001, 1511, 281-290
10. Smith, E. C. J.; Kaatz, G. W.; Seo, S. M.; Wareham, N.; Williamson, E. M.; Gibbons, S. The phenolic diterpene totarol inhibits multidrug efflux pump activity in Staphylococcus aureus Antimicrob. Agents Chemother. 2007, 51, 4480-4483
11. Jaiswal, R.; Beuria, T. K.; Mohan, R.; Mahajan, S. K.; Panda, D. Totarol inhibits bacterial cytokinesis by perturbing the assembly dynamics of FtsZ Biochemistry 2007, 46, 4211-4220
12. Evans, G. B.; Furneaux, R. H.; Gravestock, M. B.; Lynch, G. P.; Scott, G. K. The synthesis and antibacterial activity of totarol derivatives. Part 1: modifications of ring-C and pro-drugs Bioorg. Med. Chem. 1999, 7, 1953-1964
13. Evans, G. B.; Furneaux, R. H.; Gainsford, G. J.; Murphy, M. P. The synthesis and antibacterial activity of totarol derivatives. Part 3: modification of ring-B Bioorg. Med. Chem. 2000, 8, 1663-1675
14. Evans, G. B.; Furneaux, R. H. The synthesis and antibacterial activity of totarol derivatives. Part 2: modifications at C-12 and O-13 Bioorg. Med. Chem. 2000, 8, 1653-1662
15. Kim, M. B.; Shaw, J. T. Synthesis of antimicrobial natural products targeting FtsZ: (+)-totarol and related totarane diterpenes Org. Lett. 2010, 3324-3327
16. Krawczuk, P. J.; Schöne, N.; Baran, P. S. A Synthesis of the Carbon Skeleton of Maoecrystal V Org. Lett. 2009, 11, 4774-4776
17. He, L.; Liu, Y.; Shi, J.; Pei, Q. Synthesis and antitumor activity of cholest-4α-methyl-7-en-3β-ol derivatives Steroids 2006, 71, 476-483
18. Parra-Delgado, H.; Compadre, C. M.; Ramirez-Apan, T.; Munoz-Fambuena, M. J.; Compadre, R. L.; Ostrosky-Wegman, P.; Martinez-Vazquez, M. Synthesis and comparative molecular field analysis (CoMFA) of argentatin B derivatives as growth inhibitors of human cancer cell lines Bioorg. Med. Chem. 2006, 14, 1889-1901
19. Li, J. F.; Zhao, Y.; Cai, M. M.; Li, X. F.; Li, J. X. Synthesis and evaluation of a novel series of heterocyclic oleanolic acid derivatives with anti-osteoclast formation activity Eur. J. Med. Chem. 2009, 44, 2796-2806
20. Csuk, R.; Schwarz, S.; Siewert, B.; Kluge, R.; Ströhl, D. Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives Eur. J. Med. Chem. 2011, 46, 5356-5369
21. Bultman, M. S.; Ma, J.; Gin, D. Y. Synthetic Access to the Chlorocyclopentane Cores of the Proposed Original and Revised Structures of Palau'amine Angew. Chem., Int. Ed. 2008, 47, 6821-6824
22. Li, X.; Yeung, C. H.; Chan, A. S. C.; Yang, T. K. New 1,3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones Tetrahedron: Asymmetry 1999, 10, 759-763
23. LogP values for totarol (1) and azatotarol (16) were calculated using Molinspiration Property Calculation Service (www.molinspiration.com, accessed on August 10, 2012). These values are 6.4 and 4.6, respectively, suggesting that 16 has higher aqueous solubility than 1.
24. Shenvi, R. A.; Corey, E. J. Synthetic Access to Bent Polycycles by Cation-π Cyclization Org. Lett. 2010, 12, 3548-3551
25. Moore, J. T.; Soldi, C.; Fettinger, J. C.; Shaw, J. T. Catalytic alkene cyclization reactions for the stereoselective synthesis of complex "terpenoid-like" heterocycles. Chem. Sci., submitted for publication.
26. Edstrom, E.; Livinghouse, T. New methods for the generation of episulfonium ions. An application to the synthesis of carbocycles via sulfenium ion promoted arene-alkene cyclizations J. Am. Chem. Soc. 1986, 108, 1334-1336
27. Cook, M. J.; Fletcher, M. J. E.; Gray, D.; Lovell, P. J.; Gallagher, T. Highly stereoselective addition of organo-zinc reagents to pentopyranose derived glycals: Effect of protecting group and assignment of C-glycoside stereochemistry Tetrahedron 2004, 60, 5085-5092
28. Gu, W.; Wang, S. Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid Eur. J. Med. Chem. 2010, 45, 4692-4696
29. Srinivasa, A.; Mahadevan, K. M.; Varma, P. P.; Sudhakara, A. Antimony (III) sulfate catalyzed one-pot synthesis of 2,3-disubstituted indoles Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 1843-1853
30. Tiyanont, K.; Doan, T.; Lazarus, M. B.; Fang, X.; Rudner, D. Z.; Walker, S. Imaging peptidoglycan biosynthesis in Bacillus subtilis with fluorescent antibiotics Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 11033-8
31. Coan, K. E. D.; Shoichet, B. K. Stoichiometry and Physical Chemistry of Promiscuous Aggregate-Based Inhibitors J. Am. Chem. Soc. 2008, 130, 9606-9612
32. Feng, B. Y.; Shoichet, B. K. A detergent-based assay for the detection of promiscuous inhibitors Nat. Protoc. 2006, 1, 550-553
33. Anderson, D. E.; Kim, M. B.; Moore, J. T.; O'Brien, T. E.; Sorto, N. A.; Grove, C. I.; Lackner, L. L.; Ames, J. B.; Shaw, J. T. ACS Chem. Biol. 2012, in press