Semisynthetic modifications of hemiaminal function at ornithine unit of mulundocandin, towards chemical stability and antifungal activity

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 23, 2003, Pages 5189-5198

  Lal, Bansi ^a   Gund, Vitthal Genbhau ^a,b   Gangopadhyay, Ashok Kumar ^a   Nadkarni, S R ^a   Dikshit, Vidula ^a   Chatterjee, D K ^a   Shirvaikar, R ^a  

^a Piramal Enterprises Limited   (India)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CARBON NITROGEN MONOCYCLE; ETHER; FLUCONAZOLE; LIPOPEPTIDE; MULUNDOCANDIN; MULUNDOCANDIN DERIVATIVE; N1 [12 BENZYLOXY 23 [1,2 DIHYDROXY 2 (4 HYDROXYPHENYL)ETHYL] 2,11,15 TRIHYDOXY 6 (1 HYDROXYETHYL) 20 HYDROXYMETHYL 16 METHYL 5,8,14,19,22,25 HEXAOXOPERHYDRODIAZOLO[2,1 C:2,1][1,4,7,10,13,16]HEXAAZACYCLOHENICOSIN 9 YL] 12 METHYLTETRADECANAMIDE; N1 [23 [1 HYDROXY 2 (4 HYDROXYPHENYL) 2 METHOXYETHYL] 2,11,15 TRIHYDROXY 6 (1 HYDROXYETHYL) 20 HYDROXYMETHYL 12 METHOXY 16 METHYL 5,8,14,19,22,25 HEXAOXOPERHYDRODIAZOLO[2,1 C:2,1][1,4,7,10,13,16]HEXAAZACLOHENICOSIN 9 YL] 12 METHYLTETRADECANAMIDE; N1 [23 [1,2 DIHYDOXY 2 (4 HYDROXYPHENYL)ETHYL] 2,11,15 TRIHYDOXY 6 (1 HYDROXYETHYL) 20 HYDROXYMETHYL 12 METHOXY 16 METHYL 5,8,14,19,22,25 HEXAOXOPERHYDRODIAZOLO[2,1 C:2,1][1,4,7,10,13,16]HEXAAZACYCLOHENICOSIN 9 YL] 12 METHYLTETRADECANAMIDE; N1 [23 [1,2 DIHYDROXY 2 (4 HYDROXYPHENYL)ETHYL] 2,11,12,15 TETRAHYDROXY 6,1 HYDROXYETHYL 20 HYDROXYMETHYL 16 METHYL 5,8,14,19,22,25 HEXAOXOPERHYDRODIAZOLO[2,1 C:2,1][1,4,7,10,13,16]HEXAAZACYCLOHENICOSIN 9 YL] 12 METHYLTETRADECANAMIDE; N1 [23 [1,2 DIHYDROXY 2 (4 HYDROXYPHENYL)ETHYL] 2,11,15 TRIHYDROXY 6 (1 HYDROXYETHYL) 20 HYDROXYMETHYL 16 METHYL 5,8,14,19,22,25 HEXAOXO 12 PHENYLSULFANYLPERHYDRODIAZOLO[2,1 C:2,1][1,4,7,10,13,16]HEXAAZACYCLOHENICOSIN 9 YL] 12 METHYLTETRADECANAMIDE; ORNITHINE DERIVATIVE; OXYGEN DERIVATIVE; SULFIDE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; BIOASSAY; CANDIDA ALBICANS; CANDIDIASIS; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ASPERGILLUS; ASPERGILLUS FUMIGATUS; CANDIDA; CANDIDA ALBICANS;

EID: 0242266504     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.08.003     Document Type: Article

References (40)

1. (a) Walsh T.J., Jarrosinski P.F., Fromtling R.A. Diagn. Microbiol. Infect. Dis. 13:1990;37
2. (b) Samonis G., Bafaloukos D. In vivo. 6:1992;183
3. (c) Pizzo P.A., Young L.S. Am. J. Med. 76:1984;101
4. (d) Walsh T.J., Gonzalez C., Lyman C.A., Chanock S.J., Pizzo P.A. Adv. Pediatr. Infect. Dis. 11:1996;187.
5. (a) Walsh T. J. Hematol. Oncol. Clin. North Am. 7:1993;1003
6. (b) Warnock D.W. J. Antimicrob. Chemother. 36(Suppl B):1995;73
7. (c) Buchner T., Roos N. Ann. Hematol. 65:1992;153
8. (d) Dean D.A., Burchard K.W. Am. J. Surg. 171:1996;374
9. (e) Khan Z.K., Gyanchandani A. PINSA-B: Proc. Indian Natl. Sci. Acad., Part B. 64:1998;1
10. (f) Powderly W.G. J. Phys. Assoc. AIDS Care. 1994;32.
11. Gallis H.A., Drew R.H., Pickard W.W. Rev. Inf. Dis. 12:1990;308.
12. Bailey E.M., Drakovsky D.J., Ryback M.J. Pharmacotherapy. 10:1990;146.
13. (a) Fox R., Neal K.R., Leen C.L.S., Ellis M.E., Mandal B.K. J. Infect. 22:1991;201
14. (b) Smith D., Boag F., Midgley J., Gazzard B. J. Infect. 23:1991;345
15. (c) Hitchcock C.A., Pye G.W., Trok F.J., Johnson E.M., Warnock D.W. Antimicrob. Agents Chemother. 37:1993;1962
16. (d) Sanglard D., Kuchler K., Ischer F., Pagani J.-L., Monod M., Bille J. Antimicrob. Agents Chemother. 39:1995;2378
17. (e) Marybeth F., Barrett J.F. Expert Opin. Invest. Drugs. 7:1998;175. (a review with 221 refs).
18. (a) Debono M., Turner W.W., LaGrandeur L., Burkhardt F.J., Nissen J.S., Nichols K.K., Rodriguez M.J., Zweifel M.J., Zekner D.J., Gordee R.S., Tang J., Parr T.R. Jr. J. Med. Chem. 38:1995;3271
19. (b) Masurekar P.S., Fountoulakis J.M., Hallada T.C., Sosa M.S., Kaplan L. J. Antibiot. 45:1992;1867
20. (c) Iwamoto T., Fujie A., Nitta K., Hashimoto S., Okuhara M., Kohsaka M. J. Antibiot. 47:1994;1092.
21. Debono M., Gordee R.S. Ann. Rev. Microbiol. 48:1994;471.
22. Pound M.W., Drew R.H., Perfect J.R. Curr. Opin. Infect. Dis. 15:2002;183.
23. (a) Ablordeppey S.Y., Fan P., Ablordeppey J.H., Mardenborough L. Curr. Med. Chem. 6:1999;1151. (A review with 537 refs)
24. (b) Green L.J., Marder P., Mann L.L., Chio L.-C., Current W.L. Antimicrob. Agents Chemother. 43:1999;830
25. (c) Tomishima M., Ohki H., Yanada A., Takasugi H., Maki K., Tawara S., Tanaka H. J. Antibiot. 52:1999;674.
26. Hawser S., Borgonovi M., Markus A., Isert D. J. Antibiot. 52:1999;305.
27. Bouffard F.A., Hammond M.L., Arison B.H. Tetrahedron Lett. 36:1995;1405.
28. (a) Balkovec, J. M.; Bouffard, F. A.; Dropinski, J. F. (Merck and Co. Inc., USA). PCT. Int. Appl. WO 9,613,272, 9 May 1996.
29. (b) Balkovec, J. M.; Christian, R. M. (Merck and Co., Inc.). Eur. Pat. Appl. EP 459,564, 4 Dec. 1991.
30. (c) Bouffard, F. A. (Merck and Co., Inc., USA). Eur. Pat. Appl. EP 538,002, 21 Apr. 1993.
31. (d) Bouffard, F. A.; Dropinski J. F. (Merck and Co., Inc. USA). Eur. Pat. Appl. EP 539,088, 28 Apr. 1993.
32. (e) Belyk, K. M.; Bender, D. R.; Black, R. M.; Hughes, D. L.; Leonard, W. (Merck and Co., Inc.). US 5,552,521, 03 Sep. 1996.
33. (f) Boffard, F. A. (Merck and Co., Inc.). PCT, WO 96/22784, 01 Aug. 1996.
34. (a) Lal, B: Gund, V. G.; Gangopadhyay, A. K. (Aventis Pharma Deutschland G.m.b.H., Germany). PCT Int. Appl., WO 0107468 A2 200110201, 2001.
35. (b) Gund, V. G. Semisynthetic Studies On Mulundocandin: An Antifungal Lipopeptide. PhD Thesis, Nov 2001, Indian Institute Of Technology, Bombay, India.
36. (a) Zaugg H.E. Synthesis. 2:1970;49 (b) Zaugg H.E. Synthesis. 1984;85 (c) Zaugg H.E. Synthesis. 1984;181 (d) Speckamp W.N., Hiemstra H. Tetrahedron. 41:1985;4367.
37. Bouffard F.A., Zambias R.A., Dropinski J.F., Balkovec J.M., Hammond M.L., Abruzzo G.K., Bartizal K.F., Marrinan J.A., Powels M.A., Schmatz D.M. J. Med. Chem. 37:1994;222.
38. (a) Barry, A. L. Procedure and Therotical Considerations for Testing Antimicrobial Agents in Agar Media. In Antibiotics in Laboratory Medicine, 3rd ed., Lorian V. ed., Williams and Wilkins: Baltimore, MD, 1991; p 16.
39. (b) Denning D.W., Radford S.A., Oakley K.L., Hall L., Johnson E.M., Warnock D.W. J. Antimicrob. Chemother. 40:1997;401.
40. (a) Walsh T.J., Lee J.W., Kelly P., Bacher J., Lecciones J., Thomas V., Lyman C., Coleman D., Gordee R., Pizzo P.A. Antimicrob. Agents Chemother. 35:1991;1321 (b) Nawada R., Amitani R., Tanaka E., Niimi A., Suzuki K., Murayama T., Kuze F. J. Clin. Microb. 34:1996;1433 (c) Valentin A., Guennec R.L., Rodriguez E., Reynes J., Mallie M., Bastide J.-M. Antimicrob. Agents Chemother. 40:1996;1342 (d) Bartizal K., Abruzzo G., Trainor C., Krupa D., Nollstadt K., Schmatz D., Hammond M., Balkovec J., Van Middlesworth F. Antimicrob. Agents Chemother. 36:1992;1648.