Watanabe S, Ueda T
Nucleic Acids Symp Ser. 1980(8):s21-4.
Treatment of 2',3',5'-tri-O-acetyl-7-deazaadenosine with C1SCN gave the 7-thiocyanato derivative, which was converted to 7-methylthio and 7-methyl-sulfone derivatives. The thio-Claisen rearrangement and desulfurization of 7-allylthio derivative afforded 7-propyl-7-deazaadenosine. The 7-methylsulfone derivative gave the 8-cyano compound by treatment with NaCN. The action of nitrating agent on triacetyltubercidin gave a mixture of the 7- and 8-nitro derivatives. The Mannich reaction of tubercidin gave the 7-morpholinomethyl derivative which was converted to the methyl, formyl, hydroxymethyl, or cyano derivatives in good yield. The conversion of tubercidin to toyocamycin was thus accomplished. Some physical and biological properties of these substituted tubercidins were presented.
用C1SCN处理2',3',5'-三-O-乙酰基-7-脱氮腺苷得到7-硫氰酸酯衍生物，该衍生物可转化为7-甲硫基和7-甲基砜衍生物。7-烯丙硫基衍生物的硫代克莱森重排和脱硫反应得到7-丙基-7-脱氮腺苷。7-甲基砜衍生物经NaCN处理得到8-氰基化合物。硝化剂作用于三乙酰杀结核菌素得到7-硝基和8-硝基衍生物的混合物。杀结核菌素的曼尼希反应得到7-吗啉甲基衍生物，该衍生物可高产率地转化为甲基、甲酰基、羟甲基或氰基衍生物。杀结核菌素向丰加霉素的转化由此完成。文中介绍了这些取代杀结核菌素的一些物理和生物学性质。
