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Pregled bibliografske jedinice broj: 1003514

Novel Tetracyclic Imidazole Derivatives: Synthesis, Dynamic NMR Study, and Anti-Inflammatory Evaluation


Rupčić, Renata; Modrić, Marina; Hutinec, Antun; Čikoš, Ana; Stanić, Barbara; Mesić, Milan; Pešić, Dijana; Merćep, Mladen
Novel Tetracyclic Imidazole Derivatives: Synthesis, Dynamic NMR Study, and Anti-Inflammatory Evaluation // Journal of heterocyclic chemistry, 47 (2010), 640-656 doi:10.1002/jhet.376 (međunarodna recenzija, članak, znanstveni)


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Naslov
Novel Tetracyclic Imidazole Derivatives: Synthesis, Dynamic NMR Study, and Anti-Inflammatory Evaluation
(Novel tetracyclic imidazole derivatives: Synthesis, dynamic NMR study, and anti-inflammatory evaluation)

Autori
Rupčić, Renata ; Modrić, Marina ; Hutinec, Antun ; Čikoš, Ana ; Stanić, Barbara ; Mesić, Milan ; Pešić, Dijana ; Merćep, Mladen

Izvornik
Journal of heterocyclic chemistry (0022-152X) 47 (2010); 640-656

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
tetracyclic imidazole derivative, synthesis, NMR

Sažetak
A series of tetracyclic imidazole derivatives 9a–9v and 10a–10h are prepared by multistep route start- ing from the known tricyclic diketones 2a–2d. Intermediary dibenzooxepin[4, 5-d]imidazoles (3a, 3c) and dibenzothiepin[4, 5-d]imidazoles (3b, 3d) are N-protected to 4e, 4f and to the isomeric compounds 5a, 5b and 6a, 6b. The isomeric compounds 5 and 6 are separated. Compounds 4, 5, and 6 are formy- lated at C(2) to afford 7a–7j. In the last steps, aldehyde group is reduced, then alkylated to the two sets of isomeric x-dimethylaminoalkyl derivatives 9a–9v. N-deprotection of 9i–9v led to the compounds 10a–10h. Assignment of the syn/anti structure to 5a and 6a was supported by 1D selective ROESY NMR spectra, whereas conformational mobility for the selected representatives 8a and 8b is studied by and 16.2 kcal/mol, respectively. A series of derivatives 9 and 10 were tested in vitro for their anti- dynamic NMR. Activation energies (energy barriers for interconversion) are determined to be ?11.5 inflammatory activity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Ustanove
Fidelta d.o.o.

Citiraj ovu publikaciju

Rupčić, Renata; Modrić, Marina; Hutinec, Antun; Čikoš, Ana; Stanić, Barbara; Mesić, Milan; Pešić, Dijana; Merćep, Mladen
Novel Tetracyclic Imidazole Derivatives: Synthesis, Dynamic NMR Study, and Anti-Inflammatory Evaluation // Journal of heterocyclic chemistry, 47 (2010), 640-656 doi:10.1002/jhet.376 (međunarodna recenzija, članak, znanstveni)
Rupčić, R., Modrić, M., Hutinec, A., Čikoš, A., Stanić, B., Mesić, M., Pešić, D. & Merćep, M. (2010) Novel Tetracyclic Imidazole Derivatives: Synthesis, Dynamic NMR Study, and Anti-Inflammatory Evaluation. Journal of heterocyclic chemistry, 47, 640-656 doi:10.1002/jhet.376.
@article{article, year = {2010}, pages = {640-656}, DOI = {10.1002/jhet.376}, keywords = {tetracyclic imidazole derivative, synthesis, NMR}, journal = {Journal of heterocyclic chemistry}, doi = {10.1002/jhet.376}, volume = {47}, issn = {0022-152X}, title = {Novel tetracyclic imidazole derivatives: Synthesis, dynamic NMR study, and anti-inflammatory evaluation}, keyword = {tetracyclic imidazole derivative, synthesis, NMR} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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