Stille <i>vs.</i> Suzuki – cross-coupling for the functionalization of diazocines

Walther, Melanie; Kipke, Waldemar; Renken, R.L.; Staubitz, Anne

doi:10.1039/d3ra02988c

RSC Adv.

2023

DOI: 10.1039/d3ra02988c

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Stille vs. Suzuki – cross-coupling for the functionalization of diazocines

Melanie Walther

Waldemar Kipke

R.L. Renken

et al.

Abstract: Efficient syntheses towards stannylated and borylated diazocines are presented which are subsequently employed in Stille and Suzuki cross-coupling reactions.

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2024

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Cited by 2 publications

References 38 publications

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Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

Camerin,

Maleeva,

Gomila

et al. 2024

Angewandte Chemie

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A problem of systemic pharmacotherapy is off‐target activity, which causes adverse effects. Outstanding examples include neuroinhibitory medications like antiseizure drugs, which are used against epilepsy and neuropathic pain but cause systemic side effects. There is a need of drugs that inhibit nerve signals locally and on‐demand without affecting other regions of the body. Photopharmacology aims to address this problem with light‐activated drugs and localized illumination in the target organ. Here, we have developed photoswitchable derivatives of the widely prescribed antiseizure drug carbamazepine. For that purpose, we expanded our method of ortho azologization of tricyclic drugs to meta/para and to N‐bridged diazocine. Our results validate the concept of ortho cryptoazologs (uniquely exemplified by Carbazopine‐1) and bring to light Carbadiazocine (8), which can be photoswitched between 400‐590 nm light (using violet LEDs and halogen lamps) and shows good drug‐likeness and predicted safety. Both compounds display photoswitchable activity in vitro and in translucent zebrafish larvae. Carbadiazocine (8) also offers in vivo analgesic efficacy (mechanical and thermal stimuli) in a rat model of neuropathic pain and a simple and compelling treatment demonstration with non‐invasive illumination.

show abstract

Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

Camerin,

Maleeva,

Gomila

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

Camerin,

Maleeva,

Gomila

et al. 2024

Angew Chem Int Ed

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show abstract

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Stille vs. Suzuki – cross-coupling for the functionalization of diazocines

Abstract: Efficient syntheses towards stannylated and borylated diazocines are presented which are subsequently employed in Stille and Suzuki cross-coupling reactions.

Cited by 2 publications

References 38 publications

Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

Photoswitchable Carbamazepine Analogs for Non‐Invasive Neuroinhibition In Vivo

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