Concise Synthesis and X-Ray Crystal Structure of N-Benzyl-2-(pyrimidin-4′-ylamino)-thiazole-4-carboxamide (Thiazovivin), a Small-Molecule Tool for Stem Cell Research

Abstract

Stem cell research is one of the most promising fields of modern biomedical research and regenerative medicine. Limited availability and ethical concerns suggest the renouncement of embryonic stem cells (ESCs), thus raising the need for more efficient procedures for the generation of stem cells, ideally through reprogramming of mammalian cells. The small molecule N-benzyl-2-(pyrimidin-4′-ylamino)-thiazole-4-carboxamide (thiazovivin) is known to improve the generation of human induced pluripotent stem cells (iPSCs) from human fibroblasts. We herein describe a highly efficient procedure for the synthesis of thiazovivin over just five steps, which should be suitable for a large-scale application, and the first x-ray crystal structure of the target compound.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• Chemical biology
• heterocycles
• stem cells

ACKNOWLEDGMENTS

The authors thank Benjamin Groß (Hannover Medical School, Germany) for helpful discussions and the Fonds der Chemischen Industrie (FCI, Sachkostenzuschuss) for financial support. M. G. and D. S. thank the Danish National Research Foundation (DNRF)–funded Center for Materials Crystallography (CMC).