Synthesis and Biological Evaluation of Quinocarcin Derivatives

Hiromitsu SAITO; Shigeru KOBAYASHI; Youichi UOSAKI; Akira SATO; Kazuhisa FUJIMOTO; Katunori MIYOSHI; Tadashi ASHIZAWA; Makoto MORIMOTO; Tadashi HIRATA

doi:10.1248/cpb.38.1278

Hiromitsu SAITO, Shigeru KOBAYASHI, Youichi UOSAKI, Akira SATO, Kazuhisa FUJIMOTO, Katunori MIYOSHI, Tadashi ASHIZAWA, Makoto MORIMOTO, Tadashi HIRATA

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Keywords: quinocarcin, 10-halo quinocarcin derivative, DX-52-1, 10-substituted DX-52-1 analog, cyanation, electrophilic substitution, antitumor activity

JOURNAL FREE ACCESS

1990 Volume 38 Issue 5 Pages 1278-1285

DOI https://doi.org/10.1248/cpb.38.1278

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Abstract

Cyanation of quinocarcin readily opened the oxazolidine ring to provide DX-52-1 (2), which was a key compound in the synthesis of quinocarcin derivatives. Various electrophilic reactions toward aromatic ring of DX-52-1 were examined, and 10-substituted (e.g., halogen, nitro, formyl, cyano, hydroxy, etc.) analogs were prepared. Dehydrocyanation of the derivatives could be achieved to reproduce the oxazolidine ring upon treatment with HCl or AgNO₃. 10-Chloride 10 and 10-bromide 11 were the most promising among the derivatives prepared. Antitumor activity of 10 was extended to B-16 melanoma.

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