Synthesis and evaluation of anthelmintic and cytotoxic properties of [2,5']bis-1,3-azole analogs of bengazoles

Letters in Drug Design and Discovery

Volumn 6, Issue 6, 2009, Pages 413-419

  Scarone, Laura ^a   Fajardo, José ^a   Saldaña, Jenny ^a   Domínguez, Laura ^a   Espósito, Pablo ^a   Demastteis, Sylvia ^a   Wipf, Peter ^b   Manta, Eduardo ^a   Serra, Gloria ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Anthelmintic; Bengazoles; Bis 1,3 azoles; Cytotoxic

Indexed keywords

ALBENDAZOLE; ANTHELMINTIC AGENT; BENGAZOLE A; HETEROCYCLIC COMPOUND; MITOMYCIN C; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTHELMINTIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LARVA; NIPPOSTRONGYLUS BRASILIENSIS; NONHUMAN; PRIORITY JOURNAL;

EID: 69549086912     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018009789057553     Document Type: Article

References (55)

1. a) Newman, D. J.; Cragg, G. M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod., 2007, 70, 461-477.
2. b) Zhong, J. Imidazole, oxazole and thiazole alkaloids. Nat. Prod. Rep., 2006, 23, 464-496.
3. a) Riego, E.; Hernández, D.; Albericio F.; Álvarez, M. Directly linked polyazoles: important moieties in natural products. Synthesis, 2005, 1907-1922. b) Yeh, V. S. C. Recent advances in the total syntheses of oxazole-containing natural products. Tetrahedron, 2004, 60, 11995-12042. (Pubitemid 41138626)
4. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. Hennoxazoles, bioactive bisoxazoles from a marine sponge. J. Am. Chem. Soc., 1991, 113, 3173-3174.
5. a) Adamczeski, M.; Quiñoa, E.; Crews, P. Unusual anthelmintic oxazoles from a marine sponge. J. Am. Chem. Soc., 1988, 110, 1598-1602. (Pubitemid 18066748)
6. b) Rodríguez, J.; Nieto, R.; Crews, P. New Structures and Bioactivity Patterns of Bengazole Alkaloids from a Choristid Marine Sponge. J. Nat. Prod., 1993, 56, 2034-2040. (Pubitemid 24034008)
7. c) Rudi, A.; Kashman, Y.; Benayahu, Y.; Scleyer, M. Amino acid derivatives from the marine sponge Jaspis digonoxea. J. Nat. Prod., 1994, 57, 829-836.
8. a) Searle, P. A.; Molinski, T. F. Phorboxazoles A and B: potent cytostatic macrolides from marine sponge Phorbas species. J. Am. Chem. Soc., 1995, 117, 8126-8131.
9. b) Searle, P. A.; Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. Absolute configuration of phorboxazoles A and B from the marine sponge phorbas sp. 1. Macrolide and hemiketal rings. J. Am. Chem. Soc., 1996, 118, 9422-9423. (Pubitemid 26355139)
10. For oxazoline oxidation: a) Evans, D. L.; Minster, D. K.; Jordis, U.; Hecht, S. M.; Mazzu, A. L. Jr.; Meyers, A. I. Nickel peroxide de-hydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocycles. J. Org. Chem., 1979, 44, 497-501.
11. b) Barrish, J. C.; Singh, J.; Spergel, S. H.; Han, W.-C.; Kissick, T. P.; Kronenthal, D. R.; Mueller, R. H. Cupric bromide mediated oxidation of 4-carboxyoxazolines to the corresponding oxazoles. J. Org. Chem., 1993, 58, 4494-4496.
12. c) Meyers, A. I.; Tavares, F. Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. application of the kharasch-sosnovsky reaction. X. J. Org. Chem., 1996, 61, 8207-8215. (Pubitemid 26400934)
13. d) Williams, D. R.; Lowder, P. D.; Gu, Y.-G.; Brooks, D. A. Studies of mild dehydrogenations in heterocyclic systems. Tetrahedron Lett., 1997, 38, 331-334.
14. For oxazoline preparation: a) Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor. Org. Lett., 2000, 2, 1165-1168.
15. b) Williams, D. R.; Brooks, D. A.; Berliner, M. A. Total Synthesis of (-)-Hennoxazole A. J. Am. Chem. Soc., 1999, 121, 4924-4925.
16. c) Wipf, P.; Venkatraman, S. J. Org. Chem., 1995, 60, 7224.
17. d) Wipf, P.; Miller, C. P. An investigation of the Mitsunobu reaction in the preparation of peptide oxazolines, thiazolines, and aziridines. Tetrahedron Lett., 1992, 33, 6267-6270.
18. e) Wipf, P.; Lim, S. J. Total synthesis of the enantiomer of the antiviral marine natural product hennoxazole A. J. Am. Chem. Soc., 1995, 117, 558-559.
19. f) Boyce, R. J.; Mulqueen, G. C. Pattenden, G. Total synthesis of thiangazole, a novel naturally occurring HIV-1 inhibitor from Polyangium sp. Tetrahedron, 1995, 51, 7321-7330.
20. g) Downing, S. V.; Aguilar, E.; Meyer, A. I. Total Synthesis of Bistratamide D. J. Org. Chem., 1999, 64, 826-831.
21. h) Evans, D. A.; Gage, J. R.; Leighton, J. L. Total synthesis of (+)-calyculin A.. J. Am. Chem. Soc., 1992, 114, 9434-9453.
22. i) Alonso, D. A.; Bertilsson, S. K.; Johnsson, S. Y.; Nordin, S. J. M. Södergren, M. J.; Andersson, P. G. New expedient route to both enantiomers of nonproteinogenic alpha-amino acid derivatives from the unsaturated 2-aza-bicyclo moiety. J. Org. Chem., 1999, 64, 2276-2280.
23. j) Lee, S.-H.; Yoon, J.; Nakamura, K.; Lee, Y.-S. Efficient syntheses and ring-opening reactions of trans- and cis-oxazoline-5-carboxylates Org. Lett., 2000, 2, 1243-1246.
24. Mulder, Roger J.; Shafer, Cynthia M.; Molinski, Tadeusz F. First total synthesis of bengazole A. J. Org. Chem., 1999, 64, 4995-4998.
25. Chittari, P.; Hamada, Y.; Shioiri, T. A synthetic approach to bengazoles: A synthesis of deacylbengazole. Heterocycles, 2003, 59, 465-472.
26. Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B. Chem. Eur. J., 2007, 13, 5515-5538. (Pubitemid 47160163)
27. Mori, T.; Takakashi, K.; Kashiwabara, M; Uemura, D.; Katayama, C; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Structure of oxazolomycin, a novel β-lactone antibiotic. Tetrahedron Lett. ,1985, 26, 1073-1076. (Pubitemid 15131816)
28. Shiomi, K.; Arai, N.; Shinose, M.; Takahashi, Y.; Yoshida, H.; Iwabuchi, J.; Tanaka, Y.; Omura, S. New antibiotics phthoxazolins B, C and D produced by Streptomyces sp. KO-7888. J. Antibiot., 1995, 48, 714-719. (Pubitemid 26016915)
29. Henkel, T.; Zeeck, A. Secondary substances from chemical screening. 16. Inthomycins, new oxazole trienes from Streptomyces sp. Liebigs Ann. Chem., 1991, 367-373.
30. a) Schöllkopf, U.; Gerhart, F. Carbonyl olefination with alpha-metalated isocyanides. Angew. Chem. In. Ed. Engl., 1968, 7, 805-806.
31. b)Schöllkopf, U.; Schröder, R. Syntheses with alpha-metalated isocyanides. 10. 2-Unsubstituted oxazoles from alpha-metalated isocyanides and acylating agents. Angew. Chem. In. Ed. Engl., 1971, 10, 333.
32. van Leusen, A.M.; Hoogenboom, B.E.; Siderius, H. A novel and efficient synthesis of oxazoles from tosylmethylisocyanide and carbonyl compounds. Tetrahedron Lett., 1972, 23, 2369-2372.
33. a) Serra, G.; González, D.; Manta, E. A Controlled Stepwise Oxidation of Ethyl 2-Oxothiazolidine-4-carboxylate to the Corresponding 2-Hydroxythiazole. Heterocycles, 1995, 41, 2701-2711.
34. b)Gordon, S.; Costa, L.; Incerti, M.; Manta, E.; Saldaña, J.; Domínguez, L.; Mariezcurrena, R.; Suescun, L. Synthesis and in vitro anthelmintic activity against Nippostrongylus brasiliensis of new 2-amino-4-hydroxy-δ-valerolactam derivatives. Il Farmaco, 1997, 52, 603-608. (Pubitemid 28067932)
35. c) Manta, E.; Scarone, L.; Hernández, G.; Mariezcurrena, R.; Suescun, L.; Brito, I.; Brouard, I.; González, M.C.; Pérez, R.; Martín, J.D. A facile synthesis of an oxatricyclic trans.syn.trans- substituted oxepanyl framework. Tetrahedron Lett., 1997, 38, 5853-5856.
36. d) Serra, G.; Mahler, G.; Manta, E. Synthesis of methyl 2-(1′,1′-Dimethyl-2′-oxopropyl)thiazole-4-carboxylate and related 2,4-disubstituted thiazoles. Key intermediates in the synthesis of anthelmintic agents based on marine natural product. Heterocycles, 1998, 48, 2035-2048. (Pubitemid 128658951)
37. e) Mahler, S. G.; Serra, G. L.; Antonow, D.; Manta, E. Deoxo-Fluor-mediated cyclodehydration of β-hydroxy thioamides to the corresponding thiazolines. Tetrahedron Lett., 2001, 42, 8143-8146. (Pubitemid 33001329)
38. f) Scarone, L.; Sellanes, D.; Manta, E.; Wipf, P.; Serra, G. Use of deoxo-fluor for double cyclization to bis-thiazolines. Limitations of this agent for the synthesis of oxazolines. Heterocycles, 2004, 63, 773-778.
39. g) Sellanes, D.; Scarone, L.; Mahler, G.; Manta, E.; Baz, A.; Dematteis, S.; Saldaña, J.; Dominguez, L.; Wipf, P.; Serra, G. Synthesis and evaluation of anthelmintic and cytotoxic properties of bis-1,3-azole analogs of natural products. Lett. Drug Des. Discov., 2006, 3, 625-632.
40. h) Mahler, G.; Serra, G.; Dematteis, S.; Saldaña, J.; Domínguez, L.; Manta, E. Synthesis and biological evaluation of simplified mycothiazole analogues. Bioorg. Med. Chem. Lett., 2006, 16, 1309-1311. (Pubitemid 43143012)
41. i) Sellanes, D.; Manta, E.; Serra, G. Toward the total synthesis of Scleritodermin A: preparation of the C1-N15 fragment. Tetrahedron Lett., 2007, 48, 1827-1830.
42. j) Incerti, M.; Fontana, C.; Scarone, L.; Moyna, G.; Manta, E. A facile synthesis of cycloether systems bearing [2,4]-oxazole units. Heterocycles 2008, 75, 1385-1396.
43. a) Robinson, R. A new synthesis of oxazole derivatives. J. Chem. Soc., 1909, 95, 2167-2174.
44. b) Gabriel, S. Synthese von oxazolen und thiazolen II. Chem. Ber., 1910, 43, 1283-1287.
45. Nakao, R.; Oka, K.; Fukumoto, T. A simple method for the esterification of carboxylic acids using chlorosilanes. Bull. Chem. Soc. Jpn., 1981, 54, 1267-1268.
46. Davies, J. R.; Kane, P. D.; Moody, C. J. N-H Insertion reactions of rhodium carbenoids. Part 5: A convenient route to 1,3-azoles. Tetrahedron, 2004, 60, 3967-3977.
47. TosMIC is commercially available or can be prepared from sodium p-toluenesulphinate as reported: van Leusen, A. M.; Boerma, G. J. M.; Helmholdt, R. B.; Siderius, H.; Strating, J. Chemistry of sulfonylmethylisocyanides. Simple synthetic approaches to a new versatile chemical building block. Tetrahedron Lett., 1972, 23, 2367-2367
48. Chakrabarty, M.; Basak, R.; Harigaya, Y.; Takayanagi, H. Reaction of 3/2-formylindoles with TOSMIC: formation of indolyloxazoles and stable indolyl primary enamines. Tetrahedron, 2005, 61, 1793-1801. (Pubitemid 40174948)
49. White, J. M.; Tunoori, A. R.; Turunen, B. J.; Georg, G. I. [Bis(2-methoxyethyl)amino]sulfur trifluoride, the deoxo-fluor reagent: application toward one-flask transformations of carboxylic acids to amides. J. Org. Chem., 2004, 69, 2573-2576.
50. Kangani, C. O.; Kelley, D. E.; Day, B.W. One pot direct synthesis of oxazolines, benzoxazoles, and oxadiazoles from carboxylic acids using the deoxo-fluor reagent. Tetrahedron Lett., 2006, 47, 6497-6499.
51. Williams, D. R.; Lowder, P. D.; Gu, Y-G.; Brooks, D. A. Studies of mild dehydrogenations in heterocyclic systems. Tetrahedron Lett., 1997, 38, 331-334.
52. Wipf, P.; Miller, C. P.; Venkatraman, S.; Fritch, P. C. Thiolysis of oxazolines: A new, selective method for the direct conversion of peptide oxazolines into thiazolines. Tetrahedron Lett., 1995, 36, 6395-6398.
53. Jenkins, D. C.; Armitage, R.; Carrington, T. S. A new primary screening test for anthelmintics utilizing the parasitic stages of Nippostrongylus brasiliensis, in vitro. Z. Parasitenkd., 1980, 63, 261-269.
54. Skehan, P. Cytotoxicity and Cell Growth Assays. In Cell Biology A Laboratory Handbook, 2nd ed.; Academic Press: San Diego, 1998; Vol. 1, p. 331.
55. Rees, D. C.; Congreve, M.; Murray, C. W.; Carr, R. Fragment-based lead discovery. Nat. Rev. Drug Discov., 2004, 3, 660-672.