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77953685027
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note
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3): 171.05, 158.18, 137.03, 136.62, 130.05, 129.09 (2C), 128.40 (2C), 127.32, 126.78, 124.66, 123.92, 116.74, 62.99, 49.30, 39.90, 31.91, 29.89, 20.52, 20.18, 14.14, 14.03.
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77953684874
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note
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3): 170.95, 143.533, 137.11, 132.12, 131.64, 129.16, 128.94, 126.07, 125.59, 125.46, 124.48, 122.63, 121.22, 56.41, 43.14, 27.79, 19.42, 14.32.
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77953687174
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note
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In an exercise to demonstrate uniqueness, virtual libraries for all four scaffolds were enumerated with Symyx Draw 3.2 (comprising scaffold 1-168 compounds; 2-168 compounds, 3-144 compounds, 4-48 compounds). The parent structure of each compound was then compared with the 375,000 compounds available in the NIH molecular libraries small molecule repository (MLSMR) described by pharmacophore fingerprints using PowerMV v0.61. A total of 1043 similar compounds were selected using a Tanimoto Similarity function as implemented in the nearest neighbor search tool in PowerMV (distance threshold for library 1 and 2 = 0.5; library 3 = 0.29; library 4 = 0.4). The libraries and the MLSMR subset (1571 compounds total) were imported into MOE (Molecular Operating Environment v2009.11, Chemical Computing Group) and represented by structural fingerprints (MACCS keys). Tanimoto similarities were computed based on the MACCS keys, which generated a 1571 by 1571 matrix. The columns of the matrix were used as input for a principle component analysis and the first three principle components were represented graphically using MOE (Fig. 4).
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