Synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions

Chaudhuri, Naba K.; Ball, Thomas J.

doi:10.1002/jlcr.2580180814

Cited by 7 publications

(6 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We recently improved the yield of the C–C coupling through addition of bromine as an oxidizing agent [27]. The reaction times thus are reduced to several minutes as compared to several hours in previous procedures using oxygen and the yields are increased from 65% to 95% in the parent system [30].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

Moormann¹,

Langbehn²,

Herges³

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Seven symmetrically 3,3’-substituted diazocines were synthesized. Functional groups include alcohol, azide, amine and vinyl groups, which are suitable for polymer synthesis. Upon irradiation at 385 and 530 nm the diazocines perform a reversible, pincer-type movement switching the 3,3’-distance between 6.1 Å (cis, stable isomer) and 8.2 Å (trans, metastable isomer). Key reactions in the synthesis are an oxidative C–C coupling of 2-nitrotoluenes (75–82% yield) and a reductive ring closure to form the diazocines (56–60% yield). The cyclization of the dinitro compound to the azo compound was improved in yield and reproducibility, by over-reduction to the hydrazine and reoxidation to the azo unit. In contrast to 3,3’- and 4,4’-diaminodiazocine, which have been implemented in macromolecules for conformation switching, our compounds exhibit improved photophysical properties (photostationary states, separation of absorption bands in the cis and trans configuration). Hence they are promising candidates as molecular switches in photo and mechanoresponsive macromolecules and other smart materials.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

Moormann¹,

Langbehn²,

Herges³

2019

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…[19] The bridged diazocine 5 based on a nitroindane structure was synthesized analogous to the method discussed before. However, due to the fact that two different nitroaryl components are reacting with each other, the formation of four products was expected: homo addition of 1, homo addition of 6 (forming meso 8 and racemic 9) and addition of 1 with 6 (forming the racemate of 7).…”

Section: Diazocine Synthesesmentioning

confidence: 99%

Diazocines on Molecular Platforms

2014

View full text Add to dashboard Cite

show abstract

“…These approaches are based on oxidative C-C couplings of nitrotoluenes derivatives followed by reductive azo cyclization (Scheme ). − The previously published meta -benzyl alcohol diazocine 7 was synthesized by Moormann et al…”

Section: Resultsmentioning

confidence: 99%

Photoswitchable Diazocine-Based Estrogen Receptor Agonists: Stabilization of the Active Form inside the Receptor

et al. 2022

View full text Add to dashboard Cite

Photopharmacology is an emerging approach in drug design and pharmacological therapy. Light is used to switch a pharmacophore between a biologically inactive and an active isomer with high spatiotemporal resolution at the site of illness, thus potentially avoiding side effects in neighboring healthy tissue. The most frequently used strategy to design a photoswitchable drug is to replace a suitable functional group in a known bioactive molecule with azobenzene. Our strategy is different in that the photoswitch moiety is closer to the drug’s scaffold. Docking studies reveal a very high structural similarity of natural 17β-estradiol and the E isomers of dihydroxy diazocines, but not their Z isomers, respectively. Seven dihydroxy diazocines were synthesized and subjected to a biological estrogen reporter gene assay. Four derivatives exhibit distinct estrogenic activity after irradiation with violet light, which can be shut off with green light. Most remarkably, the photogenerated, active E form of one of the active compounds isomerizes back to the inactive Z form with a half-life of merely several milliseconds in water, but nevertheless is active for more than 3 h in the presence of the estrogen receptor. The results suggest a significant local impact of the ligand–receptor complex toward back-isomerization. Thus, drugs that are active when bound but lose their activity immediately after leaving the receptor could be of great pharmacological value because they strongly increase target specificity. Moreover, the drugs are released into the environment in their inactive form. The latter argument is particularly important for drugs that act as endocrine disruptors.

show abstract

Synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions

Cited by 7 publications

References 5 publications

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

Diazocines on Molecular Platforms

Photoswitchable Diazocine-Based Estrogen Receptor Agonists: Stabilization of the Active Form inside the Receptor

Contact Info

Product

Resources

About