â… Study On Synthesis Of 10-substituted Benzylideneanthrone And Their Anti-cancer Activity â…¡Study On The Process For The Synthesis Of Anabolic Hormone Oxandrolone

The first part of this dissertation study on the synthesis of 10-substituted benzylideneanthrone as a kind of novel anti-cancer drug, the relationship of structure and anti-cancer activity is also investigated.1. Eighteen 10-substituted benzylideneanthrone including six new compounds were prepared by reacting anthrone with aryl aldehyde under basic solvent in the presence of base catalyst. We find anthrone is oxidated easily by oxygen from air when pyridine is used as solvent in the presence of piperidine as catalyst, and the oxidation can be restrained effectively by adding 4-methoxy-phenol as antioxidant in reaction; By the aid of X-ray, the crystal structure of 10-2,5-dimethoxy benzylideneanthrone was determined, the whole molecule is not co-planar because the rotation of 2,5-dimethoxyphenyl ring is restricted, as a result, there exist in two optically active forms.2. The anti-cancer activity tests in vitro of the above compounds were carried on A-549 human lung cancer cells and P-388 mice leukaemia cells, and some compounds indicated intense anti-cancer activity, which is evidently stronger than the usual anti-cancer drug 5-Fu; By the analysis of their SAR, it was find that there exists a certain relationship between the substituent in the phenyl ring and it's anti-cancer activity.The second part of this dissertation study on the synthesis of oxandrolone. The whole routing include four steps: bromination, de-bromination, oxidation and reduction. Each step conditions were optimized, and the optimum conditions were determined. We find a process suitable for large-scale production, and the whole yield reach 30.2%, the structure of product was identified by IR and 'HNMR,...