Indenoindoles and cyclopentacarbazoles as bioactive compounds: Synthesis and biological applications

Rongved, Pål; Kirsch, Gilbert; Bouaziz, Zouhair; Jose, Joachim; Borgne, Marc Le

doi:10.1016/j.ejmech.2013.08.049

Cited by 46 publications

(26 citation statements)

References 77 publications

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“…The benzothiophene analogue 21 was prepared following ak nown procedure by selectiveS uzuki cross-coupling of 2,3-dibromothiophenew ith o-bromophenylboronic acid. [35] The cascade reactions under typicalr eaction conditions led to the expectedi ndeno[1,2-b]indoles 24 [36] …”

Section: Resultsmentioning

confidence: 99%

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Barroso

Cabal

Badía‐Laiño

et al. 2015

Chemistry A European J

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The Pd-catalyzed reaction between 2,2'-dibromobiphenyls and related systems with tosylhydrazones gives rise to new π-extended conjugated polycarbo- and heterocycles through an autotandem process involving a cross-coupling reaction followed by an intramolecular Heck cyclization. The reaction shows wide scope regarding both coupling partners. Cyclic and acyclic tosylhydrazones can participate in the process. Additionally, a variety of aromatic and heteroaromatic dibromoderivatives have been employed, leading to an array of diverse scaffolds featuring a fluorene or acridine central nucleus, and containing binaphthyl, thiophene, benzothiophene and indole moieties. The application to appropriate tetrabrominated systems led to greater structural complexity through two consecutive autotandem cascades. The photophysical properties of selected compounds were studied through their absorption and emission spectra. Fluorescence molecules featuring very high quantum yields were identified, showing the potential of this methodology in the development of molecules with interesting optoelectronic properties.

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Section: Resultsmentioning

confidence: 99%

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Barroso

Cabal

Badía‐Laiño

et al. 2015

Chemistry A European J

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“…Those compounds belong to different chemical scaffolds such as indeno [1,2-b]indoles, benzofuran derivatives, benzoquinones, tetracyclic benzoxanthone, anthracenedione, and flavonoid derivatives. Most of these compounds had been published as inhibitors of different kinases [29][30][31][32][33][34][35][36][37][38][39]. In order to identify the most promising compound candidates, we decided first to apply an in silico screening of our in-house library.…”

Section: Inhibitor Identificationmentioning

confidence: 99%

Development of an in vitro screening assay for PIP5K1α lipid kinase and identification of potent inhibitors

et al. 2020

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AbbreviationsAKT, protein kinase B; AR, androgen receptor; CRPC, castration-resistant prostate cancer; LIF, laser-induced fluorescence; MOPS, 3-(Nmorpholino)propane sulfonic acid; mTOR, mammalian target of rapamycin; PARP, poly(ADP-ribose) polymerase; PCa, prostate cancer; PI(4) P, phosphatidylinositol-4-phosphate; PIP 2 , phosphatidylinositol-4,5-bisphosphate; PIP5K1a, phosphatidylinositol-4-phosphate-5-kinase type 1a; PTEN, phosphatase and tensin homolog; TSP, Tris/sodium deoxycholate/1-propanol.Inhibition of PIP5K1a by pyranobenzoquinones K. Str€ atker et al.

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“…organ preservation). [1] Indeno [1,2-b]indoles are the most studied isomers, and recently, functionalized indeno [1,2-b]indol-10-ones were developed as protein kinase CK2 inhibitors. [2][3][4] CK2 is a ubiquitous serine/threonine kinase highly conserved in eukaryotic cells.…”

Section: Introductionmentioning

confidence: 99%

¹H and ¹³C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

Chab

Fenêt

Borgne

et al. 2013

Magnetic Reson in Chemistry

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Indenoindoles and cyclopentacarbazoles as bioactive compounds: Synthesis and biological applications

Cited by 46 publications

References 77 publications

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Development of an in vitro screening assay for PIP5K1α lipid kinase and identification of potent inhibitors

¹H and ¹³C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

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Indenoindoles and cyclopentacarbazoles as bioactive compounds: Synthesis and biological applications

Cited by 46 publications

References 77 publications

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Structurally Diverse π‐Extended Conjugated Polycarbo‐ and Heterocycles through Pd‐Catalyzed Autotandem Cascades

Development of an in vitro screening assay for PIP5K1α lipid kinase and identification of potent inhibitors

1H and 13C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives

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¹H and ¹³C NMR assignments of bioactive indeno[1,2‐b]indole‐10‐one derivatives