948040-78-6Relevant articles and documents
New photochromic azoderivatives with potent acetylcholinesterase inhibition
Arroyo Ma?ez, Pau,Biscussi, Brunella,Murray, Ana Paula,Richmond, Victoria,Sequeira, Maria Alejandra
, (2021)
The design of photochromic cholinesterase inhibitors is a challenge of the photopharmacological approach towards the remote control of acetylcholinesterase (AChE) enzyme and its potential application in Alzheimer's disease therapy. In this work, a series of azoderivatives were designed, synthesized and evaluated as AChE inhibitors. The optimized microwave-assisted synthesis (two steps) showed excellent yields with a total reaction time no longer than 40 min. The results showed that all the synthesized compounds exhibited high AChE inhibitory activity at the micromolar range (IC50, 0.65–8.52 μM). Moreover, compound 19, with double four-hydrocarbon chain connected to piperidine, showed a powerful in vitro enzymatic response for its Z isomer (IC50: 0.43 μM) determined by Ellman's assay. Also, 19 showed a stable photostationary state monitored by UV/Vis absorption spectroscopy and 1H NMR spectra. These results indicate that 19 can act as an efficient photo-responsible probe to remote control AChE activity. Molecular modelling analysis of 19 Z revealed its affinity by the peripheral anionic site of AChE, providing understanding of its higher inhibition power. This study contributes to the development of new promising agents for photopharmacological treatment of Alzheimer's disease.
Effect of Structure of Photoresponsive Molecules on Photochemical Phase Transition of Liquid Crystals I. Synthesis and Thermotropic Properties of Photochromic Azobenzene Derivatives
Ikeda, T.,Miyamoto, T.,Kurihara, S.,Tsukada, M.,Tazuke, S.
, p. 357 - 371 (2007/10/02)
Seventeen azobenzene derivatives were synthesized and their thermotropic properties were examined.They are classified into three groups.In the first group, 4-cyanobiphenyl moieties are attached to both sides of azobenzene through various alkyl spacers: AB(nCB)2 where n = 3, 4, 5 and 6.In the second group, the 4-cyanobiphenyl moiety is attached to one side of the azobenzene, while the substituent of the other side was kept as OCH3:1ABnCB, where n = 3, 4, 5, 6 and 8.The third group is the azobenzene derivatives which possess alkoxy substituents at both para positions of azobenzene (nABm) or at various positions of the azobenzene phenyl rings (k,1ABn,m).The introduction of the 4-cyanobiphenyl group at the end(s) of the molecules is based on the attempt of highly efficient photochromic molecules to induce photochemical phase transition of liquid crystals by providing the photochromic trigger molecules with high affinity to the host liquid crystal.Both 1ABnCB and AB(nCB)2 exhibited the liquid crystalline phases, whereas among nABm and k,1ABn,m, only 1AB8 and 8AB8 showed the liquid crystalline phase.The 1ABnCB series exhibited a distinct odd-even variation in phase transition temperatures as well as enthalpy and entropy changes with the length of the flexible spacers, while the AB(nCB)2 series did not show clear odd-even variation except for the liquid crystal to isotropic phase transition temperatures.
