Microbial biotransformations of a synthetic immunomodulating agent, HR325

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 7, 1997, Pages 1369-1380

  Lacroix, Isabelle ^a   Biton, Jacques ^b   Azerad, Robert ^a  

^a CNRS   (France)

^b SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; HR 325; IMMUNOMODULATING AGENT; RU 34941; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG METABOLISM; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORAL DRUG ADMINISTRATION; RAT; ULTRAVIOLET SPECTROPHOTOMETRY;

ADJUVANTS, IMMUNOLOGIC; ANILINE COMPOUNDS; BIOTRANSFORMATION; FUNGI;

ANIMALIA; BASSIANA; BEAUVERIA; CORDYCEPS BASSIANA; CUNNINGHAMELLA ELEGANS; FUNGI; MORTIERELLA; UMBELOPSIS ISABELLINA;

EID: 0030791735     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00094-1     Document Type: Article

References (52)

1. Smith, R. V.; Rosazza, J. P. Arch. Biochem. Biophys. 1974, 161, 551.
2. Smith, R. V.; Rosazza, J. P. J. Pharm. Sci. 1975, 11, 1737.
3. Rosazza, J. P. Lloydia 1978, 41, 279.
4. Rosazza, J. P.; Smith, R. V. Adv. Appl. Microbiol. 1979, 25, 169.
5. Smith, R. V.; Rosazza, J. P. In Microbial Transformations of Bioactive Compounds; Rosazza, J. P., Ed.; CRC Press: Boca Raton, FL, 1982; pp 1-42.
6. Smith, R. V.; Rosazza, J. P. J. Nat. Prod. 1983, 46, 79.
7. Clark, A. M.; McChesney, J. D.; Hufford, C. D. Med. Res. Rev. 1985, 5, 23.
8. Davis, P. J. Dev. Ind. Microbiol. (J. Ind. Microbiol. suppl. No 3) 1988, 29, 197.
9. Kouzi, S. A.; Mcchesney, J. D. J. Nat. Prod.-Lloydia 1991, 54, 483.
10. Borchert, H. H. Arch. Pharm. 1991, 324, 401.
11. Griffiths, D. A.; Best, D. J.; Jezequel, S. G. Appl. Microbiol. Biotechnol. 1991, 35, 373.
12. Chen, T. S.; Arison, B. H.; Wicker, L. S.; Inamine, E. S. J. Antibiotics 1992, 45, 577.
13. Hufford, C. D.; Elsharkawy, S. H.; Jürgens, T. M.; Mikell, J. R. Pharmaceut. Res. 1992, 9, 623.
14. Yang, W.; Davis, P. J. Drug Metab. Dispos. 1992, 20, 38.
15. Chen, T. S.; Doss, G. A.; Hsu, A.; Hsu, A.; Lingham, R. B.; White, R. F.; Monaghan, R. L. J. Nat. Prod.-Lloydia 1993, 56, 755.
16. Hammoumi, A.; Girault, J.-P.; Azerad, R.; Revial, G.; D'Angelo, J. Tetrahedron Asymmetry 1993, 4, 1295.
17. Hezari, M.; Davis, P. J. Drug Metab. Dispos. 1993, 21, 259.
18. Khalifa, S. I.; Baker, J. K.; Rogers, R. D.; Elferaly, F. S.; Hufford, C. D. Pharmaceut. Res. 1994, 11, 990.
19. Cannell, R. P.; Knaggs, A. R.; Dawson, M. J.; Manchee, G. R.; Eddershaw, P. J.; Waterhouse, I.; Sutherland, D. R.; Bowers, G. D.; Sidebottom, P. J. Drug Metab. Dispos. 1995, 23, 724.
20. Seven steps, starting from 4-trifluoromethyl-3-toluidine, were required to afford in a poor yield (less than 25%) the desired alcohol derivative RU34941. Moreover, this synthesis was not adapted for the preparation of a radioactive compound.
21. Dupront, A. 1995, personal communication.
22. Petzoldt, K.; Kieslich, K.; Steinbeck, H. German Patent 1974, no. 2,326,084.
23. Kieslich, K.; Vidic, H. J.; Petzoldt, K.; Hoyer, J. A. Chem. Ber. 1976, 109, 2259.
24. Neef, G.; Eder, U.; Petzoldt, K.; Seeger, A.; Wieglepp, H. J. Chem. Soc. Chem. Commun. 1982, 366.
25. Vigne, B.; Archelas, A.; Fourneron, J. D.; Furstoss, R. Tetrahedron 1986, 42, 2451.
26. Vigne, B.; Archelas, A.; Furstoss, R. Tetrahedron 1991, 47, 1447.
27. Gallant, M.; Link, J. T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 343.
28. Holland, H. L. Organic synthesis with oxidative enzymes; VCH: New York, 1992.
29. Holland, H. L.; Kindermann, M.; Kumaresan, S.; Stefanac, T. Tetrahedron: Asymmetry 1993, 4, 1353.
30. Krow, G. R. In Organic Reactions; Paquette, L. A., Ed.; 1993; Vol. 43, pp 251-798.
31. Walsh, C. T.; Chen, Y.-C. J. Angew. Chem. Int. Ed. Engl. 1988, 27, 333.
32. Azerad, R.; Buisson, D.; Maillot, S.; Ouazzani-Chahdi, J. In Bioorganic Chemistry in Healthcare and Technology (NATO symposium); Pandit, U. K.; Alderweireldt, F. C., Eds.; Plenum: New York, 1991; pp 233-236.
33. Alphand, V.; Archelas, A.; Furstoss, R. J. Org. Chem. 1992, 57, 1306.
34. Rasmussen, J. K. Synthesis 1977, 91.
35. Brownbridge, P. Synthesis 1983, 1.
36. Wasserman, H. H.; Pickett, J. E. J. Am. Chem. Soc. 1982, 104, 4695.
37. Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299.
38. Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880.
39. Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y. Tetrahedron Lett. 1985, 26, 3563.
40. Hassner, A.; Reuss, R. H.; Pinnick, H. W. J. Org. Chem. 1975, 40, 3427.
41. Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
42. Chenault, H. K.; Danishefsky, S. J. J. Org. Chem. 1989, 1989, 4249.
43. Adam, W.; Hadjiarapoglou, L.; Klicic, J. Tetrahedron Lett. 1990, 31, 6517.
44. Adam, W.; Golsch, D.; Hadjiarapoglou, L. J. Org. Chem. 1991, 56, 7292.
45. Guertin, K. R.; Chan, T.-H. Tetrahedron Lett. 1991, 32, 715.
46. Adam, W.; Prechtl, F. Chem. Ber. 1991, 124, 2369.
47. Adam, W.; Müller, M.; Prechtl, F. J. Org. Chem. 1994, 59, 2358.
48. Lacroix, I.; Biton, J.; Azerad, R., unpublished results.
49. Chen, L. J.; Hecht, S. S.; Peterson, L. A. Chem. Res. Toxicol. 1995, 8, 903.
50. Ueng, Y. F.; Shimada, T.; Yamazaki, H.; Guengerich, F. P. Chem. Res. Toxicol. 1995, 8, 218.
51. Halcomb, R. L.; Danishefski, S. J. J. Am. Chem. Soc. 1989, 111, 6661.
52. Gordon, D. M.; Danishefski, S. J.; Samuel, J. J. Org. Chem. 1991, 56, 3713.