Relationship between structure and biological activity of novel R106 analogs

Journal of Antibiotics

Volumn 49, Issue 4, 1996, Pages 386-389

  Rodriguez, Michael J ^a   Zweifel, Mark J ^a   Farmer, James D ^a   Gordee, Robert S ^a   Loncharich, Richard J ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; PASINIAZID; SARCOSINE;

ALKYLATION; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA; CANDIDA ALBICANS; CANDIDA GLABRATA; CANDIDA PARAPSILOSIS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG HYDROXYLATION; DRUG POTENCY; DRUG STRUCTURE; HYDROGEN BOND; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

EID: 0029864831     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.49.386     Document Type: Article

References (12)

1. YOSHIKAWA, Y.; K. IKAI, Y. UMEDA, A. OGAWA, K. TAKESAKO, I. KATO & H. NAGANAWA: Isolation, sturcture, and antifungal activities of new aureobasidins. J. Antibiotics 46: 1347-1354, 1993
2. TAKESAKO, K.; H. KURODA, T. INOUE, F. HARUNA, Y. YOSHIKAWA, I. KATO, K. UCHIDA, T. HIRATANI & H. YAMAGUCHI: Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J. Antibiotics 46: 1414-1420, 1993
3. IKAI, K.; K. TAKESAKO, K. SHIOMI, M. MORIGUCHI, Y. UMEDA, J. YAMAMOTO, I. KATO & H. NAGANAWA: Structure of aureobasidin A. J. Anitbiotics 44: 925-933, 1991
4. IKAI, K.; K. SHIOMI, K. TAKESAKO, S. MIZUTANI, J. YAMAMOTO, Y. OGAWA, M. UENO & I. KATO: Structures of aureobasidins B to R. J. Anitbiotics 44: 1187-1198, 1991
5. YAMAGUCHI, H.; T. NAKAMURA, K. UCHIDA, K. TAKESAKO, K. IKAI, J. YAMAMOTO & K. SHIMANAKA (Takara Shuzo): Preparation of R106 analogs as medicinal fungicides. U.S. 5200505, 1993
6. AWAZU, N.; K. IKAI, J. YUMAMOTO, K. NISHIMURA, S. MIZUTANI, K. TAKESAKO & I. KATO: Structures and antifungal activities of new aureobasidins. J. Antibiotics 48: 525-527, 1995
7. TAKESAKO, K.; K. IKAI, K. SHIMANAKA, J. YAMAMOTO, F. HARUNA, T. NAKAMURA, H. YAMAGUCHI & K. UCHIDA (Takara Shuzo): Preparation of antibacterial antibiotic R106 (cyclic peptide) derivatives. JP 03044398, 1989.
8. BALKOVEC, J. M.; Lipopeptide antifungal agents. Expert Opin. Invest. Drugs 3: 65-82, 1994
9. FUJIKAWA, A.; Y. IN, M. INOUE & T. ISHIDA: X-ray and NMR conformational study of aureobasidin E: a cyclic depsipeptide with potent antifungal activity. J. Org. Chem. 59: 570-578, 1994
10. ISHIDA, T.; Y. IN, A. FUJIKAWA, H. URATA, M. INOUE, K. IKAI, K. TAKESAKO & I. KATO: Conformational feature of aureobasidin E, a new type of potent antifungal antibiotic. J. Chem. Soc., Chem. Comm. 17: 1231-1233, 1992
11. RODRIGUEZ, M. J.; M. J. ZWEIFEL & R. J. LONCHARICH: Aldol promoted reaction of R106-sarcosine: Synthesis and conformational analysis of New R106 analogs. Journal of Organic Chemistry, 1996, in press
12. KUROME, T.; K. INAMI, T. INOUE, K. IKAI, K. TAKESAKO, I. KATO & T. SHIBA: Total synthesis of aureobasidin A, an antifungal cyclic depsipeptide. Chem. Lett. 11:1873-1876, 1993