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Relevant academic research and scientific papers

A Simple and Versatile Strategy for Rapid Color Fading and Intense Coloration of Photochromic Naphthopyran Families

Benzo-annulated chromenes, i.e., naphthopyrans, are well-known photochromic molecules that undergo photochemical ring-opening reactions to form two colored open-ring isomers, the transoid-cis and transoid-trans forms, upon light irradiation. Though the transoid-cis form returns thermally to the uncolored closed form, the fading rate of the transoid-trans form is extremely slow because of its higher thermal stability. This slow fading behavior of the transoid-trans form is responsible for the persistence of residual color for several minutes to hours, and prevents the application of such molecules to fast photoswitching materials. We have found a new simple and versatile strategy to substantially reduce the amount of the undesirable long-lived colored transoid-trans form by introducing an alkoxy group at the 1-position of azino-fused chromenes, i.e., 8H-pyranoquinazolines. The alkoxy group effectively reduces the formation of the transoid-trans form due to C-H···O intramolecular hydrogen bonding in the transoid-cis form. Moreover, the introduction of a condensed aromatic ring at the 3-position was found to be effective to increase the photosensitivity of the ring-opening reaction. This strategy can also be applied for naphthopyran derivatives and is useful for the development of fast photoresponsive photochromic lenses and fast photoswitching applications such as dynamic holographic materials and molecular actuators.

PYRANOQUINAZOLINE DERIVATIVES AND NAPHTHOPYRAN DERIVATIVES

[Problem] A problem is presented in that conventional photochromic compounds cannot be considered adequate in terms of the colorizing/decolorizing rate and durability, and the production process therefore has many steps. The present invention provides an industrially applicable photochromic compound that has both a rapid colorizing/decolorizing reaction and high durability and can also be synthesized at a low cost. [Solution] This compound is characterized in that etheric oxygen atoms are bonded to the carbon atoms at position 1 of a pyranoquinazoline (8H-pyrano[3,2-f]quinazoline) skeleton and position 10 of a naphthopyran (3H-naphtho[2,1-b]pyran) skeleton, said compound having photochromic properties and being a photochromic compound that has both a rapid colorizing/decolorizing reaction and high durability. Also provided is an industrially applicable photochromic compound that can be synthesized at a low cost.

Discovery of Highly Selective and Nanomolar Carbamate-Based Butyrylcholinesterase Inhibitors by Rational Investigation into Their Inhibition Mode

Butyrylcholinesterase (BChE) is a promising target for the treatment of later stage cognitive decline in Alzheimer's disease. A set of pseudo-irreversible BChE inhibitors with high selectivity over hAChE was synthesized based on carbamates attached to tetrahydroquinazoline scaffolds with the 2-thiophenyl compound 2p as the most potent inhibitor of eqBChE (KC = 14.3 nM) and also of hBChE (KC = 19.7 nM). The inhibitors transfer the carbamate moiety onto the active site under release of the phenolic tetrahydroquinazoline scaffolds that themselves act as neuroprotectants. By combination of kinetic data with molecular docking studies, a plausible binding model was probed describing how the tetrahydroquinazoline scaffold guides the carbamate into a close position to the active site. The model explains the influence of the carrier scaffold onto the affinity of an inhibitor just before carbamate transfer. This strategy can be used to utilize the binding mode of other carbamate-based inhibitors.