Synthesis and Biological Evaluation of Quinocarcin Derivatives

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,...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1990/05/25, Vol.38(5), pp.1278-1285
Hauptverfasser: SAITO, Hiromitsu, KOBAYASHI, Shigeru, UOSAKI, Youichi, SATO, Akira, FUJIMOTO, Kazuhisa, MIYOSHI, Katunori, ASHIZAWA, Tadashi, MORIMOTO, Makoto, HIRATA, Tadashi
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Sprache:eng
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Zusammenfassung: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.38.1278