Laboratory of Pharmaceutical Organic Chemistry

1. External stimuli responsive aromatic amides and functional alteration
2. Redox-driven molecular switches
3. Spontaneous generation of chirality of the aromatic amides bearing pyrimidines

Three-dimensional structure of a molecule and its alteration is an important issue, and itis essential problem for controlling the function of a molecule such as a molecular switchor device. In most cases, molecular switches have relatively high activation energy forinterconversion between alternative structures, however in some biological systems,conformational preference plays an important role in regulation of bioactivity.

We have interested in conformational alteration of aromatic amides, which haveinteresting features about conformation. Most of secondary aromatic amides such asbenzanilide tend to prefer trans conformation, whereas N-methylation makes itsconformation cis-favored. Recently we found several aromatic amides altered thepreferred conformation depending on the external stimuli. Thus, N-phenyl- N-quinonyl typeof amides changed their preferred conformation according to redox state of quinonylmoiety. N-Methyl pyridylamides showed conformational alteration according to solventacceptor ability or addition of acid. N-Methylated pyridylamide oligomer also showedunique conformational folding and unfolding. These properties of the aromatic amides canbe applied to stimuli-responsive molecular switches and functional molecules.