Structure-activity relationship of an ozonide carboxylic acid (oz78) against fasciola hepatica

Journal of Medicinal Chemistry

Volumn 53, Issue 10, 2010, Pages 4223-4233

  Zhao, Qingjie ^a   Vargas, Mireille ^b,c   Dong, Yuxiang ^a   Zhou, Lin ^a   Wang, Xiaofang ^a   Sriraghavan, Kamaraj ^a   Keiser, Jennifer ^b,c   Vennerstrom, Jonathan L ^a  

^a NEBRASKA MEDICAL CENTER   (United States)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3 CARBOXYMETHYL 7,14,15 TRIOXADISPIRO[5.1.5.2]PENTADECANE; 5 FLUOROADAMANTANE 2 SPIRO 3' 8' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; 6 FLUOROADAMANTANE 2 SPIRO 3' 8' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; 6,6 DIFLUOROADAMANTANE 2 SPIRO 3',8' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 2',8' CARBOXYMETHYL 1',4' DIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 6' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 7' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' (2' OXO 2' HYDRAZINOETHYL) 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' [[(ETHOXY)HYDROXYPHOSPHINYL]METHYL] 1',2',4''TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' [[[(2' SULFOETHYL)AMINO]CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' [[[(CARBOXYMETHYL)AMINO]CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' [[[(METHYLSULFONYL)AMINO]CARBONYL]METHYL] 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' CARBOXYMETHYL 1',2' DIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' CARBOXYMETHYL 1',2',4' TRIOXA 8' AZASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE 2 SPIRO 3' 8' DICARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; ADAMANTANE DERIVATIVE; ANTIPARASITIC AGENT; ARTESUNATE; BICYCLO[3.3.1]NONANE 9 SPIRO 3' 8' CARBOXYMETHYL 1',2',4' TRIOXASPIRO[4.5]DECANE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; HEMOGLOBIN; OZONIDE CARBOXYLIC ACID; PRODRUG; UNCLASSIFIED DRUG;

ACIDITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG STRUCTURE; DRUG SYNTHESIS; FASCIOLA HEPATICA; FEMALE; IN VIVO STUDY; NONHUMAN; PROTEIN DEGRADATION; RAT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

ADAMANTANE; ANIMALS; ANTHELMINTICS; FASCIOLA HEPATICA; FASCIOLIASIS; FEMALE; RATS; RATS, WISTAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77952677684     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100226t     Document Type: Article

References (46)

1. Fenwick, A.; Keiser, J.; Utzinger, J. Epidemiology, Burden and Control of Schistosomiasis with Particular Consideration to Past and Current Treatment Trends Drugs Future 2006, 31, 413-425
2. Keiser, J.; Utzinger, J. Food-Borne Trematodiases Clin. Microbiol. Rev. 2009, 22, 466-483
3. Rojas, L.; Vazquez, A.; Domenech, I.; Robertson, L. J. Fascioliasis: Can Cuba Conquer This Emerging Parasitosis? Trends Parasitol. 2010, 26, 26-34
4. Keiser, J.; Utzinger, J. Emerging Foodborne Trematodiasis Emerging Infect. Dis. 2005, 11, 1507-1514
5. Keiser, J.; Utzinger, J. Advances in the Discovery and Development of Trematocidal Drugs Expert Opin. Drug Discovery 2007, 2, S9-S23
6. Hien, T. T.; Truong, N. T.; Minh, N. H.; Dat, H. D.; Dung, N. T.; Hue, N. T.; Dung, T. K.; Tuan, P. Q.; Campbell, J. I.; Farrar, J. J.; Day, J. N. A Randomized Controlled Pilot Study of Artesunate versus Triclabendazole for Human Fascioliasis in Central Vietnam Am. J. Trop. Med. Hyg. 2008, 78, 388-392
7. Keiser, J.; Utzinger, J. Artemisinins and Synthetic Trioxolanes in the Treatment of Helminth Infections Curr. Opin. Infect. Dis. 2007, 20, 605-612
8. Keiser, J.; Xiao, S.-H.; Dong, Y.; Utzinger, J.; Vennerstrom., J. L. Clonorchicidal Properties of the Synthetic Trioxolane OZ78 J. Parasitol. 2007, 93, 1209-1214
9. Xiao, S.-H.; Keiser, J.; Chollet, J.; Utzinger, J.; Dong, Y.; Vennerstrom., J. L.; Endriss, Y.; Tanner, M. In Vitro and in Vivo Activities of Synthetic Trioxolanes against Major Human Schistosome Species Antimicrob. Agents Chemother. 2007, 51, 1440-1445
10. Robert, A.; Benoit-Vical, F.; Claparols, C.; Meunier, B. The antimalarial drug artemisinin alkylates heme in infected mice Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 13676-13680
11. Keiser, J.; Brun, R.; Fried, B.; Utzinger, J. Trematocidal Activity of Praziquantel and Artemisinin Derivatives: In Vitro and in Vivo Investigations on Adult Echinostoma caproni Antimicrob. Agents Chemother. 2006, 50, 803-805
12. Keiser, J.; Utzinger, J.; Tanner, M.; Dong, Y.; Vennerstrom, J. L. The Synthetic Peroxide OZ78 Is Effective against Echinostoma caproni and Fasciola hepatica J. Antimicrob. Chemother. 2006, 58, 1193-1197
13. Keiser, J.; Shu-Hua, X.; Tanner, M.; Utzinger, J. Artesunate and Artemether Are Effective Fasciolicides in the Rat Model and in Vitro J. Antimicrob. Chemother. 2006, 57, 1139-1145
14. Kaiser, M.; Wittlin, S.; Nehrbass-Stuedli, A.; Dong, Y.; Wang, X.; Hemphill, A.; Matile, H.; Brun, R.; Vennerstrom, J. L. Peroxide Bond-Dependent Antiplasmodial Specificity of Artemisinin and OZ277 (RBx11160) Antimicrob. Agents Chemother. 2007, 51, 2991-2993
15. Keiser, J.; Utzinger, J. Food-Borne Trematodiasis: Current Chemotherapy and Advances with Artemisinins and Synthetic Trioxolanes Trends Parasitol. 2007, 23, 555-562
16. Keiser, J.; Utzinger, J.; Vennerstrom, J. L.; Dong, Y.; Brennan, G.; Fairweather, I. Activity of Artemether and OZ78 against Triclabendazole- Resistant Fasciola hepatica Trans. R. Soc. Trop. Med. Hyg. 2007, 101, 1219-1222
17. Tsandi, E.; Kokotos, C. G.; Kousidou, S.; Ragoussis, V.; Kokotos, G. Sulfonamides of Homoproline and Dipeptides as Organocatalysts for Michael and Aldol Reactions Tetrahedron 2009, 65, 1444-1449
18. Dong, Y.; Wittlin, S.; Sriraghavan, K.; Chollet, J.; Charman, S. A.; Charman, W. N.; Scheurer, C.; Urwyler, H.; Santo Tomas, J.; Snyder, C.; Creek, D. J.; Morizzi, J.; Koltun, M.; Matile, H.; Wang., X.; Padmanilayam, M.; Tang, Y.; Dorn, A.; Brun, R.; Vennerstrom, J. L. The Structure-Activity Relationship of the Antimalarial Ozonide Arterolane (OZ277) J. Med. Chem. 2010, 53, 481-491
19. Mock, G. A.; Holmes, A. B.; Raphael, R. A. Spirocyclic synthesis by [4+2]-cycloaddition: The Preparation of 11,13-Dioxa-1,4-dithia-12, 12,18-trimethyl-10,14,17-trioxotrispiro[4.2.0.5.4.2]eicosane Tetrahedron Lett. 1977, 18, 4539-4540
20. 4/THF mixed solvent was reported by the following: Itoh, T.; Wanibe, T.; Iwatsuki, S. Synthesis and Polymerization of 7,7-Bis(alkoxycarbonyl) -1,4-benzoquinone Methides J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 963-969
21. Griesbaum, K.; Liu, X.; Kassiaris, A.; Scherer, M. Ozonolyses of O-Alkylated Ketoximes in the Presence of Carbonyl Groups: A Facile Access to Ozonides Liebigs Ann./Recl. 1997, 1381-1390
22. Dong, Y.; Vennerstrom, J. L. Dispiro-1,2,4,5-Tetraoxanes via Ozonolysis of Cycloalkanone O -Methyl Oximes: A Comparison with the Peroxidation of Cycloalkanones in Acetonitrile Sulfuric Acid Media J. Org. Chem. 1998, 63, 8582-8585
23. Yamagishi, T.; Fujii, K.; Shibuya, S.; Yokomatsu, T. Asymmetric Synthesis of Phosphonic Acid Analogues for Acylcarnitine Tetrahedron 2006, 62, 54-65
24. Rew, Y.; McMinn, D. L.; Wang, Z.; He, X.; Hungate, R. W.; Jaen, J. C.; Sudom, A.; Sun, D.; Tu, H.; Ursu, S.; Villemure, E.; Walker, N. P. C.; Yan, X.; Ye, Q.; Powers, J. P. Discovery and Optimization of Piperidyl Benzamide Derivatives as a Novel Class of 11β-HSD1 Inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 1797-1801
25. Dziemidowicz, J.; Witt, D.; Sliwka-Kaszynska, M.; Rachon, J. Potassium Trimethylsilanolate-Mediated Conversion of Dialkyl Phosphonates to Their Anhydrous Potassium Monoalkyl Phosphonates Under Mild, Non-Aqueous Conditions Synthesis 2005, 4, 569-574
26. Padmanilayam, M.; Scorneaux, B.; Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Creek, D. J.; Charman, W. N.; Santo Tomas, J.; Scheurer, C.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Antimalarial Activity of N -Alkylamine, Carboxamide, Sulfonamide, and Urea Derivatives of a Dispiro-1,2,4-trioxolane Piperidine Bioorg. Med. Chem. Lett. 2006, 16, 5542-5545
27. Tang, Y.; Dong, Y.; Karle, J. M.; DiTusa, C. A.; Vennerstrom, J. L. Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction: Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions J. Org. Chem. 2004, 69, 6470-6473
28. Dong, Y.; Chollet, J.; Matile, H.; Charman, S. A.; Chiu, F. C. K.; Charman, W. N.; Scorneaux, B.; Urwyler, H.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Dorn, A.; Wang, X.; Karle, J. M.; Tang, Y.; Wittlin, S.; Brun, R.; Vennerstrom, J. L. Spiro and Dispiro-1,2,4-Trioxolanes as Antimalarial Peroxides: Charting a Workable SAR Using Simple Prototypes J. Med. Chem. 2005, 48, 4953-4961
29. Tang, Y.; Dong, Y.; Wittlin, S.; Charman, S. A.; Chollet, J.; Chiu, F. C. K.; Charman, W. N.; Matile, H.; Urwyler, H.; Dorn, A.; Bajpai, S.; Wang, X.; Padmanilayam, M.; Karle, J. M.; Brun, R.; Vennerstrom, J. L. Weak Base Dispiro-1,2,4-Trioxolanes: Potent Antimalarial Ozonides Bioorg. Med. Chem. Lett. 2007, 17, 1260-1265
30. Marques, C. A.; Selva, M.; Tundo, P.; Montanari, F. Reaction of Oximes with Dimethyl Carbonate: A New Entry to 3-Methyl-4,5-disubstituted-4-oxazolin-2- ones J. Org. Chem. 1993, 58, 5765-5770
31. Zhou, L.; Alker, A.; Ruf, A.; Wang, X.; Chiu, F. C. K.; Morizzi, J.; Charman, S. A.; Charman, W. N.; Scheurer, C.; Wittlin, S.; Dong, Y.; Hunziker, D.; Vennerstrom, J. L. Characterization of the Two Major CYP450 Metabolites of Ozonide (1,2,4-Trioxolane) OZ277 Bioorg. Med. Chem. Lett. 2008, 18, 1555-1558
32. Lantvoev, V. I. Synthesis of 4-Substituted Adamantane-1-carboxylic Acids Zh. Org. Khim. 1976, 12 (11) 2361-2368
33. Ayres, F. D.; Khan, S. I.; Chapman, O. L.; Kaganove, S. N. Improvements in the Synthesis of Adamantane-2,6-dione and Preparation of the Novel Adamantane-2,6-dione Mono-ketal Tetrahedron Lett. 1994, 35, 7151-7154
34. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. Iodine as a Catalyst for Efficient Conversion of Ketones to gem -Dihydroperoxides by Aqueous Hydrogen Peroxide Org. Lett. 2006, 8, 2491-2494
35. Wang, X.; Dong, Y.; Wittlin, S.; Creek, D.; Chollet, J.; Charman, S. A.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Vennerstrom, J. L. Spiro and Dispiro-1,2-dioxolanes: Contribution of Iron(II)-Mediated One-Electron vs. Two-Electron Reduction to the Activity of Antimalarial Peroxides J. Med. Chem. 2007, 50, 5840-5847
36. Ramirez, A.; Woerpel, K. A. Synthesis of 1,2-Dioxolanes by Annulation Reactions of Peroxycarbenium Ions with Alkenes Org. Lett. 2005, 7, 4617-4620
37. Farcasiu, D.; Schleyer, P. V. R.; Ledlie, D. B. Ring Enlargements by Thallium(III) Oxidation of Double Bonds. Application to Adamentane Systems J. Org. Chem. 1973, 38, 3455-3459
38. Tang, Y.; Wittlin, S.; Charman, S. A.; Chollet, J.; McClennan, D. N.; Chiu, F. C. K.; Johnson, L. M.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Zhou, L.; Dong, Y.; Charman, W. N.; Matile, H.; Urwyler, H.; Dorn, A.; Vennerstrom, J. L. The Comparative Antimalarial Properties of Weak Base and Neutral Synthetic Ozonides Bioorg. Med. Chem. Lett. 2010, 20, 563-566
39. Keiser, J. In Vitro and In Vivo Trematode Models for Chemotherapeutic Studies Parasitology 2010, 137, 589-603
40. Vennerstrom, J. L.; Arbe-Barnes, S.; Brun, R.; Charman, S. A.; Chiu, F. C. K.; Chollet, J.; Dong, Y.; Dorn, A.; Hunziker, D.; Matile, H.; McIntosh, K.; Padmanilayam, M.; Santo Tomas, J.; Scheurer, C.; Scorneaux, B.; Tang, Y.; Urwyler, H.; Wittlin, S.; Charman, W. N. Identification of an Antimalarial Synthetic Trioxolane Drug Development Candidate Nature 2004, 430, 900-904
41. Erhardt, S.; Macgregor, S. A.; McCullough, K. J.; Savill, K.; Taylor, B. J. Model Studies of β-Scission Ring-Opening Reactions of Cyclohexyloxy Radicals: Application to Thermal Rearrangements of Dispiro-1,2,4-trioxanes Org. Lett. 2007, 9, 5569-5572
42. Dong, Y.; Tang, T.; Chollet, J.; Matile, H.; Wittlin, S.; Charman, S. A.; Charman, W. N.; Santo Tomas, J.; Scheurer, C.; Snyder, C.; Scorneaux, B.; Bajpai, S.; Alexander, S. A.; Wang, X.; Padmanilayam, M.; Rao, C. S.; Brun, R.; Vennerstrom, J. L. Effect of Functional Group Polarity on the Antimalarial Activity of Spiro and Dispiro-1,2,4-Trioxolanes Bioorg. Med. Chem. 2006, 14, 6368-6382
43. Lowther, J.; Robinson, M. W.; Donnelly, S. M.; Xu, W.; Stack, C. M.; Matthews, J. M.; Dalton, J. P. The Importance of pH in Regulating the Function of the Fasciola hepatica Cathepsin L1 Cysteine Protease PLoS Neglected Trop. Dis. 2009, 3, e369
44. Halferty, L.; ONeill, J. F.; Brennan, G. P.; Keiser, J.; Fairweather, I. Electron Microscopical Study To Assess the in Vitro Effects of the Synthetic Trioxolane OZ78 against the Liver Fluke, Fasciola hepatica Parasitology 2009, 136, 1325-1337
45. Schmoldt, P.; Mattay, J. A Versatile Synthesis of Bicyclo[2.2.2]octan-2- one Derivatives Synthesis 2003, 1071-1078
46. · Groups in Cyclohexylmethyl Radicals J. Am. Chem. Soc. 1988, 110, 7494-7499