Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

Tetrahedron Letters

Volumn 53, Issue 50, 2012, Pages 6739-6742

  Baqi, Younis ^a,b   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

^b SULTAN QABOOS UNIVERSITY   (Oman)

Author keywords

Anthraquinone; Cancer; Cardiovascular; Deamination

Indexed keywords

ANTHRAQUINONE DERIVATIVE;

ARTICLE; CANCER THERAPY; CARDIOVASCULAR DISEASE; CHEMICAL REACTION; DEAMINATION; DRUG ACTIVITY; STRUCTURE ACTIVITY RELATION;

EID: 84868605609     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.09.011     Document Type: Article

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26. 2 (0.2 mmol, 2 equiv) dissolved in 0.5 mL distilled water while the temperature was kept between 0-5 °C for 5 min. The mixture was then allowed to warm up to rt, and zinc powder (10 equiv) was added together with 5 mL of ethanol, and the reaction was stirred at rt for ca. 30 s. The reaction can easily be followed due to the color change that is observed during the course of the reaction: the starting blue material turns red after diazotization while the final product has a purple color. The reaction was also followed by RP-TLC using acetone: water (2:3) as the eluent. Then the product was purified by flash column chromatography using reversed phase silica gel (RP-18) and water. The polarity of the eluent was then gradually decreased by the addition of acetone in the following steps: 5%, 20%, 40%, and 60%. Fractions containing purple product were collected. For some compounds the last step of purification (RP-18 flash chromatography) had to be repeated twice to obtain pure product (≥95% purity as determined by LC-MS/UV and elemental analysis, to an accuracy of within ±0.4%). The pooled fractions containing a purple color were collected and evaporated under vacuum until all acetone and most of the water phase were removed. The remaining water was then removed by a freeze dryer to yield products 10a-z.