Synthesis and antifungal activity of pradimicin derivatives. Modifications on the aglycone part.

S Aburaki, S Okuyama, H Hoshi, H Kamachi, M Nishio, T Hasegawa, S Masuyoshi, S Iimura, M Konishi, T Oki

Bristol-Myers Squibb Research Institute, Bristol-Myers Squibb K. K., Tokyo, Japan.

The Journal of antibiotics 1993 Sep

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Synthesis and antifungal activity of pradimicin analogs modified on the aglycone part is described. Upon modification studies at various sites of the aglycone part using pradimicin A (PRM A), C-11 position was found to be the sole site to be modified without loosing antifungal activity. Further modification studies at C-11 position were carried out with 11-OH derivative of pradimicin T1 (PRM T1) because of its easy availability. Among the compounds prepared, 11-demethoxy derivative of PRM A (12) and 11-O-ethyl (13) and 11-O-fluoroethyl (14) derivatives of PRM T1 showed promising antifungal activity comparable to that of PRM A.

Citation

S Aburaki, S Okuyama, H Hoshi, H Kamachi, M Nishio, T Hasegawa, S Masuyoshi, S Iimura, M Konishi, T Oki. Synthesis and antifungal activity of pradimicin derivatives. Modifications on the aglycone part. The Journal of antibiotics. 1993 Sep;46(9):1447-57