182951-14-0Relevant articles and documents
Molecular design, chemical synthesis and biological studies of novel enediynes related to dynemicin A
Wu, Ming-Jung,Lin, Chi-Fong,Chen, Huey-Ting,Duh, Tsai-Huey,Wang, Shan-Shue,Hsu, Shih-Chung
, p. 2183 - 2186 (2007/10/03)
Two novel enediynes 1 and 2 and related molecules containing a (Z)-7-sulfonyl-3-hepten-1,5-diyne functionality and quinoline moiety related to dynemicin A were synthesized from quinoline and 4-methoxyquinoline, respectively. The key synthetic features involve (1) magnesium acetylide addition to the 1-acylsalt of the quinolines (2) a Pd(O)-Cu(I) catalyzed coupling reaction of vinyl chloride or aryl iodide with acetylenes (3) conversion of the alcohol to a sulfide, followed by oxidation to a sulfone. These molecules proved to be active against the growth of leukemia, colon, epidermoid and melanoma cancer cell lines.