New photochromic azoderivatives with potent acetylcholinesterase inhibition

Biscussi, Brunella; Sequeira, María Alejandra; Richmond, Victoria; Máñez, Pau Arroyo; Murray, Ana Paula

doi:10.1016/j.jphotochem.2021.113375

Cited by 7 publications

(10 citation statements)

References 30 publications

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“…Dual AChE inhibitor 139 was designed through the replacement of aza-stilbene with azobenzene, followed by the duplication of the pharmacophore. [155] The resulting compound 139 displayed a (Z)-on behavior, with a F(Z/E) � 2. Molecular docking and subsequent MD simulations proposed a crucial contribution of charge-assisted hydrogen bonds between the piperidium moieties and Asp72.…”

Section: Methodsmentioning

confidence: 99%

“…In line with the scarse representation of aza-stilbenes in bioactive ligands, only in one study such moiety was replaced with azobenzene for the design of photoswitchable inhibitor 78, targeting AChE. [155] To amplify the light-induced changes in end-to-end distances, the authors also repeated the flexible alkyl chain on the other side of the photoswitch. In the dual inhibitor 130, azobenzene is better defined as a linker (see section 3.4).…”

Section: Aza-stilbene (Class 1)mentioning

confidence: 99%

“…In fact, this classic bioisosteric replacement requires the substitution of only one carbon in the −CH=N− linker, thus introducing one HBA with the nitrogen atom. In line with the scarse representation of aza‐stilbenes in bioactive ligands, only in one study such moiety was replaced with azobenzene for the design of photoswitchable inhibitor 78 , targeting AChE [155] . To amplify the light‐induced changes in end‐to‐end distances, the authors also repeated the flexible alkyl chain on the other side of the photoswitch.…”

Section: Analog Designmentioning

confidence: 99%

“…In only one reported example, a bioisosteric replacement was the starting point of a de novo design of a photoswitchable spacer. Dual AChE inhibitor 139 was designed through the replacement of aza‐stilbene with azobenzene, followed by the duplication of the pharmacophore [155] . The resulting compound 139 displayed a ( Z )‐on behavior, with a F( Z / E ) ≈2.…”

Section: Analog Designmentioning

confidence: 99%

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Rational Design in Photopharmacology with Molecular Photoswitches

et al. 2023

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Photopharmacology is an attractive approach for achieving targeted drug action with the use of light. In photopharmacology, molecular photoswitches are introduced into the structure of biologically active small molecules to allow for the optical control of their potency. Going beyond trial and error, photopharmacology has progressively applied rational drug design methodologies to devise light-controlled bioactive ligands. In this review, we categorize photopharmacological efforts from the standpoint of medicinal chemistry strategies, focusing on diffusible photochromic ligands modified with photoswitches that operate through E-Z bond isomerization. In the vast majority of cases, photoswitchable ligands are designed as analogs of existing compounds, through a variety of approaches. By analyzing in detail a comprehensive list of instructive examples, we describe the state of the art and discuss future opportunities for rational design in photopharmacology.

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Section: Methodsmentioning

confidence: 99%

Section: Aza-stilbene (Class 1)mentioning

confidence: 99%

Section: Analog Designmentioning

confidence: 99%

Section: Analog Designmentioning

confidence: 99%

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Rational Design in Photopharmacology with Molecular Photoswitches

et al. 2023

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“…52 Various phenyldiazenederived products are biologically and chemically potent compounds that have potential applications as anticancer agents, used as linkers in solid-phase organic synthesis, shows potent acetyl cholinesterase and aromatase inhibition activity. [53][54][55][56][57][58][59][60][61] Phenyldiazenyl-substituted Schiff base ligands and their metal complexes shows antibacterial, antioxidant, anti-inflammatory, and antifungal activities. [62][63][64] Oxidation of diazinyl-protected various N-heterocycles yields the corresponding functionalized lactams.…”

Section: Letter Synlettmentioning

confidence: 99%

Evaluation of Phenyldiazenyl as a Protective/Activating Group in Lithiation–Substitution Reactions of Tetrahydroisoquinolines

Singh,

Kaur,

Kaur

et al. 2023

Synlett

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Phenyldiazenyl moiety has been utilized both as a protective and activating group to synthesize C-1-substituted tetrahydroisoquinolines via lithiation–substitution strategy. This reaction sequence involves generation of α-amino carbanions, derived from N-phenyldiazenyl tetrahydroisoquinolines, followed by coupling with various electrophiles, e.g., aldehyde, ketones, alkyl halide, oxiranes, isocyanates, and with in situ generated arynes. Deprotection of the protecting group was carried out under acidic conditions to afford the desired α-substituted products in moderate to good yields. So, triazene as a protecting/directing group and its compatibility with strong bases provide a good synthetic utility for the synthesis of a variety of α-substituted secondary amines via lithiation substitution reaction.

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