Saito H, Kobayashi S, Uosaki Y, Sato A, Fujimoto K, Miyoshi K, Ashizawa T, Morimoto M, Hirata T
Kyowa Hakko Kogyo Co., Ltd., Tokyo Research Laboratories, Japan.
Chem Pharm Bull (Tokyo). 1990 May;38(5):1278-85. doi: 10.1248/cpb.38.1278.
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.
醌癌菌素的氰化反应很容易打开恶唑烷环，得到DX - 52 - 1（2），它是醌癌菌素衍生物合成中的关键化合物。研究了DX - 52 - 1芳香环上的各种亲电反应，并制备了10 - 取代（如卤素、硝基、甲酰基、氰基、羟基等）类似物。用HCl或AgNO₃处理这些衍生物可实现脱氢氰化反应，从而重现恶唑烷环。在制备的衍生物中，10 - 氯化物10和10 - 溴化物11最具前景。10的抗肿瘤活性扩展到了B - 16黑色素瘤。
