Research Article
A DFT and Semiempirical Model-Based Study of Opioid Receptor Affinity and Selectivity in a Group of Molecules with a Morphine Structural Core
Table 1
Molecules and their experimental opioid receptor binding affinitiesa,b.
| | Molecule | R1 | R2 R3 | R4 R5 | R6 | R7 | Exp. log | Exp. Log | Exp. log |
| | 1 | –CONH2 | –OH –H | =O –H | –OH | –CH2–c–Pr | −1.28 | 0.41 | −0.63 | | 2 | –CONH2 | –O– | =O –H | –OH | –CH2–c–Pr | −0.14 | 2.74 | 1.04 | | 3 | –OH | –O– | =O –H | –OH | –CH2–c–Pr | −0.95 | 1.77 | −0.72 | | 4 | –CONH2 | –OH –H | α-OH –H | –OH | –CH2–c–Bu | −0.28 | 1.89 | 0.95 | | 5 | –CONH2 | OH –H | –OH –H | –OH | –CH2–c–Bu | 0.57 | 2.17 | −0.33 | | 6 | –OH | –O– | –OH –H | –OH | –CH2–c–Bu | 0.2 | 2.76 | 0.47 | | 7 | –CONH2 | –OH –H | β-OH –H | –OH | –CH2–c–Bu | −1.14 | 0.59 | −0.46 | | 8 | –CONH2 | –OH –H | –H –H | –OH | –CH2–c–Pr | −0.79 | 0.62 | −0.53 | | 9 | –CONH2 | –O– | –H –H | –OH | –CH2–c–Pr | 0.39 | 2.79 | 1.2 | | 10 | –OH | –O– | –H –H | –OH | –CH2–c–Pr | −0.61 | 1.89 | −0.61 | | 11 | –CONH2 | –OH –H | =O –H | –H | –CH3 | −0.52 | 0.91 | 0.36 | | 12 | –CONH2 | –O– | =O –H | –H | –CH3 | 0.07 | 2.41 | 1.27 | | 13 | –OH | –O– | =O –H | –H | –CH3 | −0.55 | 1.57 | 0.44 | | 14 | –CONH2 | –OH –H |  | –H | –CH2–c–Pr | −0.29 | −1.6 | −0.09 | | 15 | –CONH2 | –O– |  | –OH | –CH2–c–Pr | 1.66 | −0.52 | 1.67 | | 16 | –OH | –O– |  | –OH | –CH2–c–Pr | 0.72 | −0.85 | 0.46 |
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aFrom [89]. bIn molecules 15–17 the carbon atoms marked with black dots belong to the common skeleton.
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