Abramson H N, Banning J W, Nachtman J P, Roginski E T, Sardessai M, Wormser H C, Wu J D, Nagia Z, Schroeder R R, Bernardo M M
J Med Chem. 1986 Sep;29(9):1709-14. doi: 10.1021/jm00159a024.
A series of anthraquinonyl glucosaminosides (10a-e) were synthesized by Koenigs-Knorr glycosidation of the corresponding aglycones (11a-e) with bromo sugar 12 followed by saponification. These glycosides were intended to serve as models to study the role played by the hydroxyl substituents on the aglycone portion of the antitumor anthracycline antibiotics. Superoxide generation as measured in rat heart sarcosomes was found to increase with the addition of successive hydroxyl groups to the anthraquinone nucleus. The 1,8-dihydroxy pattern was determined to generate significantly less superoxide than the 1,4-dihydroxy pattern. Hydroxyl substitution was also observed to stabilize the complex formed between the anthraquinones and DNA and was required for antibacterial activity against a number of Gram-positive organisms.
通过相应的苷元（11a - e）与溴代糖12进行柯尼希斯 - 克诺尔糖苷化反应，随后进行皂化反应，合成了一系列蒽醌基葡糖胺苷（10a - e）。这些糖苷旨在作为模型，用于研究羟基取代基在抗肿瘤蒽环类抗生素苷元部分所起的作用。在大鼠心肌肌粒中测量的超氧化物生成量，随着蒽醌核上连续羟基的添加而增加。已确定1,8 - 二羟基模式产生的超氧化物比1,4 - 二羟基模式显著更少。还观察到羟基取代可稳定蒽醌与DNA之间形成的复合物，并且对于针对多种革兰氏阳性菌的抗菌活性是必需的。
