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

REFERENCES

• DeWitt , N. Stem-cell biology . Nature 2006 , 441 , 1059 .
   Web of Science ®Google Scholar
• Williams , D. A. Rapid development of pluripotent stem cells as a potential therapeutic modality . Mol. Ther. 2009 , 17 , 929 – 930 .
   PubMed Web of Science ®Google Scholar
• Smith , A. A glossary for stem-cell biology . Nature 2006 , 441 , 1060 .
   Web of Science ®Google Scholar
• Hochedlinger , K. ; Jaenisch , R. Nuclear reprogramming and pluripotency . Nature 2006 , 441 , 1061 – 1067 .
   PubMed Web of Science ®Google Scholar
• Takahashi , K. ; Tanabe , K. ; Ohnuki , M. ; Narita , M. ; Ichisaka , T. ; Tomoda , K. ; Yamanaka , S. Induction of pluripotent stem cells from adult human fibroblasts by defined factors . Cell 2007 , 131 , 861 – 872 .
   PubMed Web of Science ®Google Scholar
• Yu , J. ; Vodyanik , M. A. ; Smuga-Otto , K. ; Antosiewicz-Bourget , J. ; Frane , J. L. ; Tian , S. ; Nie , J. ; Jonsdottir , G. A. ; Ruotti , V. ; Stewart , R. ; Slukvin , I. I. ; Thomson , J. A. Induced pluripotent stem cell lines derived from human somatic cells . Science 2007 , 318 , 1917 – 1920 .
   PubMed Web of Science ®Google Scholar
• Müller , L. U. W. ; Daley , G. Q. ; Williams , D. A. Upping the ante: Recent advances in direct reprogramming . Mol. Ther. 2009 , 17 , 947 – 953 .
   PubMed Web of Science ®Google Scholar
• Lin , T. ; Ambasudhan , R. ; Yuan , X. ; Li , W. ; Hilcove , S. ; Abujarour , R. ; Lin , X. ; Hahm , H. S. ; Hao , E. ; Hayek , A. ; Ding , S. A chemical platform for improved induction of human iPSCs . Nat. Methods 2009 , 6 , 805 – 808 .
   PubMed Web of Science ®Google Scholar
• Zhu , J. ; Pang , D. ; Zhou , Y. ; Tang , X. ; Huang , Y. ; Xie , W. ; Gao , F. ; Lai , L. ; Zhang , M. ; Ouyang , H. Direct conversion of porcine embryonic fibroblasts into adipocytes by chemical molecules . Cell. Reprogramming 2012 , 14 , 99 – 105 .
   PubMed Web of Science ®Google Scholar
• Xu , Y. ; Zhu , Y. ; Hahm , H. S. ; Wei , W. ; Hao , E. ; Hayek , A. ; Ding , S. Revealing a core signalling regulatory mechanism for pluripotent stem cell survival and self-renewal by small molecules . Proc. Natl. Acad. Sci. USA 2010 , 107 , 8129 – 8134 .
   PubMed Web of Science ®Google Scholar
• Chen , H. ; Wang , W. ; Wang , G. ; Shi , L. ; Gu , M. ; Ren , Y. ; Hou , L. ; He , P. ; Zhu , F. ; Zhong , X. ; Tang , W. ; Zuo , J. ; Nan , F. Rational design and synthesis of 2,2-bisheterocycle tandem derivatives as non-nucleoside hepatitis B virus inhibitors . ChemMedChem 2008 , 3 , 1316 – 1321 .
   PubMed Web of Science ®Google Scholar
• Plouvier , B. ; Houssin , R. ; Bailly , C. ; Henichart , J. P. Synthesis and DNA-binding study of a thiazole-containing analog of netropsin . J. Heterocycl. Chem. 1989 , 26 , 1643 – 1647 .
   Web of Science ®Google Scholar
• Delgado , O. ; Muller , H. M. ; Bach , T. Concise total synthesis of the thiazolyl peptide antibiotic GE2270A . Chem. Eur. J. 2008 , 14 , 2322 – 2339 .
   PubMed Web of Science ®Google Scholar
• Silberg , A. ; Ursu , A. Preparation and properties of 2-halo-4-halomethylthiazoles . Rev. Roum. Chim. 1965 , 10 , 897 – 902 .
   Google Scholar
• (a) Kottke , T. ; Stalke , D. Crystal handling at low temperatures . J. Appl. Crystallogr. 1993 , 26 , 615 – 619 ; (b) Kottke , T. ; Lagow , R. J. ; Stalke , D. Low-cost conversion of a coaxial nozzle arrangement into a stationary low-temperature attachment . J. Appl. Crystallogr . 1996 , 29 , 465 – 468 ; (c) Stalke , D. Cryo crystal structure determination and application to intermediates . Chem. Soc. Rev. 1998 , 27 , 171 – 178 .
   Web of Science ®Google Scholar
• Schulz , T. ; Meindl , K. ; Leusser , D. ; Stern , D. ; Graf , J. ; Michaelsen , C. ; Ruf , M. ; Sheldrick , G. M. ; Stalke , D. A comparison of a microfocus x-ray source and a conventional sealed tube for crystal structure determination . J. Appl. Crystallogr. 2009 , 42 , 885 – 891 .
   Web of Science ®Google Scholar
• SAINT v7.68A in Bruker APEX v2011.9 , Bruker AXS Inst. Inc. : Madison , WI , USA , 2008 .
   Google Scholar
• Sheldrick , G. M. SADABS 2008/2 ; Georg-August-University Göttingen : Germany , 2008 .
   Google Scholar
• (a) Sheldrick , G. M. Phase annealing in SHELX-90: direct methods for larger structures . Acta Crystallogr. Sect. A 1990 , 46 , 467 – 473 ; (b) Sheldrick , G. M. A short history of SHELX . Acta Crystallogr. Sect. A 2008 , 64 , 112 – 122 ; (c) Müller , P. ; Herbst-Irmer , R. ; Spek , A. L. ; Schneider , T. R. ; Sawaya , M. R. in Crystal Structure Refinement: A Crystallographer's Guide to SHELXL, IUCr Texts on Crystallography, Vol. 8; P. Müller (Ed.); Oxford University Press, Oxford, UK, 2006 ; (d) Hübschle , C. B. ; Sheldrick , G. M. ; Dittrich , B. ShelXle: a Qt graphical user interface for SHELXL . J. Appl. Crystallogr . 2011 , 44 , 1281 – 1284 .
   Web of Science ®Google Scholar