Design and Synthesis of Matrix Metalloproteinase Inhibitors Guided by

2348

J. Med. Chem. 2002, 45, 2348

2001, Volume 44 Gary L. Grunewald,* Timothy M. Caldwell, Qifang Li, and Kevin R. Criscione: Synthesis and Evaluation of 4-Fluoro-8-substituted-2,3,4,5-tetrahydro1H-2-benzazapines as Selective Inhibitors of Phenylethanolamine N-Methyltransferase versus the R2-Adrenoceptor. Page 2853. The C-F coupling constants in the following 13C NMR spectra were reported incorrectly. The values given below are the corrected coupling constants. page

compd

C-F coupling

C-F coupling

C-F coupling

2853 2853 2853 2853 2853

19 20 12‚HCl 24 25

93.3 (d, J ) 179 Hz, CHF) 136.4 (d, J ) 21 Hz, C-4) 136.9 (d, J ) 6 Hz, C-5a) 93.0 (d, J ) 176 Hz, CHF) 83.8 (d, J ) 172 Hz, CH2F)

45.1 (d, J ) 26 Hz, C-3) 82.3 (d, J ) 176 Hz, CH2F) 86.2 (d, J ) 172 Hz, CHF) 43.8 (d, J ) 26 Hz, C-3) 40.7 (d, J ) 3 Hz, C-3)

37.4 (d, J ) 24 Hz, C-5) 40.3 (d, J ) 4 Hz, C-3) 38.5 (d, J ) 23 Hz, C-5) 36.5 (d, J ) 24 Hz, C-5) 38.3 (d, J ) 20 Hz, C-4)

JM020118L 10.1021/jm020118l Published on Web 04/20/2002

Stephen Hanessian,* D. Bruce MacKay, and Nicolas Moitessier: Design and Synthesis of Matrix Metalloproteinase Inhibitors Guided by Molecular Modeling. Picking the S1 Pocket Using Conformationally Constrained Inhibitors. Page 3081. Compound 19 should be (3aR,4S,7aR)-. Compound 5h should be 3-(R)-1-Hydroxy-. Compound 5i should be 3-(S)-1-Hydroxy-. It follows that 18a is R and 18b is S, but these have not been mentioned specifically. JM020097V 10.1021/jm020097v Published on Web 04/26/2002