Synthesis and antifungal activities of alanine-exchanged analogs of pradimicin A.
A series of pradimicin analogs were designed and synthesized to investigate the effect of the amino acid side chain on the antifungal activity. The alanine-exchanged analogs (3a approximately 3q) were synthesized from 4'-N-Cbz-pradimic acid by coupling with appropriate amino acids or their equivalents followed by deblocking. All the D-alpha-amino acid derivatives except D-proline analog, 3k retained the antifungal activity.
Okuyama
S
S
Bristol-Myers Squibb Research Institute, Bristol-Myers Squibb K.K. Tokyo, Japan.
Kakushima
M
M
Kamachi
H
H
Konishi
M
M
Oki
T
T
D000409:Alanine / Q000031:analogs & derivatives; D000818:Animals; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002177:Candidiasis / Q000188:drug therapy; D051379:Mice; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D000095643:Pradimicins and Benanomicins
D000409:Alanine; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; C058036:pradimicin A; D000095643:Pradimicins and Benanomicins