Part I、Studies of structure-activity relationships of anticancer apiole analoguesPart II、Design and synthesis of potential oxazabicycle-based donor-acceptor photochromic colorants

• Main Authors: Shih-Yu, Yu, 盂施妤
• Other Authors: Ding-Yah, Yang
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/35899300572177815157

碩士 === 東海大學 === 化學系 === 102 === Part I、 This part of the thesis mainly described the structure-activity relationships of the anticancer apiole analogs against the COLO 205 cell. The structure and the relative positions of functional groups of apiole were modified and further expanded to obtain the compounds SY02, SY03, SY04, and SY06. These four compounds along with the commercial available SY01 and SY05 were then tested for their anticancer activities against COLO 205 cell by the MTT assay. The preliminary results indicated that COLO 205 cell viability was slightly decreased when treated with 100 μM of dimers SY03 and SY06. In contrast, when COLO 205 was treated with 125 μM of SY01-SY06, the monomers SY01, SY 02, SY 04, and SY 05 exhibit better inhibitory effect than that of the dimers SY03, SY 06, and apiole. Part II、This thesis mainly described the efforts to improve the photo-fatigue resistance properties of the o-nitrobenzyl substituted oxazabicycle-based photochromic colorant previously reported from our lab by replacing the o-nitrophenyl group of the oxazabicycle with other electron acceptors such as methylpyridinium or imide. Three compounds, that is, 18, 27, and 40, were designed and their attempted syntheses were described. First, in the preparation of compound 18, we encountered difficulties during the coupling of 4-hydroxycoumarin with the quinoline moiety, presumably due to the intramolecular hydrogen bonding present in the 16. An alternate synthetic pathway for the target compound has been derived, and the synthesis is still ongoing. Second, compound 27 was prepared in seven steps with overall yield of 17%. Unfortunately, the preliminary studies suggested that the synthesized compound 27 is insensitive to light and does not exhibit the expected photochromic properties. Finally, we tried to prepare compound 40 by using the similar synthetic strategy for the preparation of 27. The coupling of the imine with 3-methylbutanal was unsuccessful, presumably due to the instability of the former. Again, an alternate synthetic pathway for the target compound has been derived, and the synthesis remains ongoing.