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. Author manuscript; available in PMC: 2009 Nov 21.
Published in final edited form as: ACS Chem Biol. 2008 Nov 21;3(11):711–722. doi: 10.1021/cb800120t

Figure 1. Structure of the C5-quinazoline D156844 and its effects on cellular SMN mRNA levels.

Figure 1

The structure of D156844, a C5 substituted ether-based 2,4-diaminoquinazoline is shown with its 2-fluoro-benzyl piperidine substituent. Atoms of the quinazoline scaffold are numbered in italics. (A) Fold increase of β-lactamase in NSC34 cells treated with D156844 (mean ± SD, triplicate wells), EC50 = 9.1 nM (B) Fold increase of mouse SMN mRNA in NSC-34 cells treated with D156844, 100 nM trichostatin A (TSA) or DMSO (mean ± SD, n=9) (C) Synthesis of 125I labeled C5-quinazoline. D156469, a tin derivative was synthesized from D156156 as described in the Supplemental Text. An 125I sodium iodide /chloramine T procedure was used to displace the SnBu3 of D156469, yielding the desired radiolabeled C5-quinazoline.