Synthesis and biological evaluation of quinocarcin derivatives |
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Authors: | H Saito S Kobayashi Y Uosaki A Sato K Fujimoto K Miyoshi T Ashizawa M Morimoto T Hirata |
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Institution: | Kyowa Hakko Kogyo Co., Ltd., Tokyo Research Laboratories, Japan. |
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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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