Table 7. Hydrogen-bond and mixed π-interactions (Å) of o-nitrosulfonamides 1–3 and N-cycloamino-o-sulfanilamides 4–6 with the hCA II (PDB entry 4iwz) and hCA IX (5fl4) isoenzymes.
| Isoenzyme/Entry | Carbonic anhydrase II (PDB entry 4iwz) | Carbonic anhydrase IX (PDB entry 5fl4) | ||
|---|---|---|---|---|
| Hydrogen bond | π–π or π–cation | Hydrogen bond | π–π or π–cation | |
| o-Nitrosulfonamides | ||||
| 1 | GLN92 (2.13) | GLN92 (2.14) | HID94 (4.08) π–cation | |
| 2 | ASN62 (2.33), ASN67 (2.55) | GLN71 (2.28), THR201 (2.13) | HID94 (4.07) π–cation | |
| 3 | GLN92 (2.25), ASN62 (2.74) | TRP5 (5.36) π–π stacking | GLN71 (2.26) | HID94 (4.05) π–cation |
| N-Cycloamino-o-sulfanilamides | ||||
| 4 | GLN92 (2.04), THR199 (2.29) | THR201 (2.03) | ||
| 5 | GLN92 (1.78), THR199 (2.26) | |||
| 6 | GLN92 (1.88), TRP5 (2.11) | THR199 (1.81) π–π stacking | GLU92 (2.47) | |
| A | GLN92 (2.39), HIE64 (2.24) | HIS94 (4.75) π–π stacking | ||
| B | ASP13 (1.59–2.73), VAL130 (2.53) | HID94 (5.49) π–cation | ||
Note: A is N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-2-(thiophen-2-yl)acetamide and B is 5-[1-(naphthalen-1-yl)-1,2,3-triazol-4-yl]thiophene-2-sulfonamide.