Table 1.
Summary of the synthesized axitinib derivatives and their photochemical and biological characterization. λexc: irradiation wavelength, PSS: photostationary state, t1/2: half-life of the metastable form.
| |||||
|---|---|---|---|---|---|
| # | Residue (R) | λexc (nm) | PSS (E/Z%), DMSO (NMR) |
t1/2 (h), 37 °C, DMSO (UV/VIS) | IC50 VEGFR-2 (nM) |
| 1 |
|
385 (ZE) 365 (EZ) |
88/12 (ZE) 51/49 (EZ) |
>>12 * |
E: 19 Z: 817 PSS 385 nm: 29 |
| 2 |
|
n/a | n/a | n/a | E: 415 |
| 3 |
|
365 | 17/83 | 43.1 |
E: 1077 ** PSS 365 nm: 1289 |
| 4 |
|
385 | 20/80 | 5.7 |
E: 1020 ** PSS 385 nm: 1435 |
| 5 |
|
405 | 47/53 | 7.3 |
Z: >10,000 PSS 405 nm: 214 |
| 6 |
|
405 | 25/75 | 3.7 |
Z: >10,000 PSS 405 nm: 251 |
| 7 |
|
405 | 60/40 | 1.5 |
Z: n/a ** PSS 405 nm: 493 |
* No thermal back isomerization could be observed over 12 h. ** residual kinase activity ≥ 33%.