Construction of Polyheterocyclic
Benzopyran Library
with Diverse Core Skeletons through Diversity-Oriented Synthesis Pathway:
Part II
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Abstract
As a continuation of our previous report (<i>J.
Comb. Chem.</i> <b>2010</b>, <i>12</i>, 548β558), we accomplished the
diversity-oriented synthesis of polyheterocyclic small-molecule library
with privileged benzopyran substructure. To ensure the synthetic efficiency,
we utilized the solid-phase parallel platform and the fluorous-tag-based
solution-phase parallel platform to construct a 284-member polyheterocyclic
library with six distinct core skeletons with an average purity of
87% on a scale of 5β10 mg. This library was designed to maximize
the skeletal diversity with discrete core skeletons in three-dimensional
space and the combinatorial diversity with four different benzopyranyl
starting materials and various building blocks. Together with our
reported benzopyranyl library, we completed the construction of polyheterocyclic
benzopyran library with 11 unique scaffolds and their molecular diversity
was visualized in chemical space using principle component analysis
(PCA)