Synthesis and antiproliferative activity of new cytotoxic tri- and tetraazabenzo[3,2-a]fluorene-5,6-dione derivatives

Leepasert, Theerachart; Shahabi, Manochehr; Shanab, Karem; Schirmer, Eva; Hölzer, W.; Spreitzer, Helmut; Aicher, Babette; Müller, Gilbert; Günther, E

doi:10.1016/j.bmcl.2013.08.021

Cited by 5 publications

(2 citation statements)

References 11 publications

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“…6,7-Dichloroisoquinoline-5,8-dione was prepared by following the known procedure. 41 The following compounds (YQ-026, YQ-027, YQ-028, YQ-029, YQ-030, and YQ-031) were prepared by the same procedure for the synthesis of YQ-025.…”

Section: ■ Methodsmentioning

confidence: 99%

“…After being stirred at rt for 3 h, the reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (hexanes/ethyl acetate/dichloromethane = 3:1:2 to dichloromethane only to dichloromethane/MeOH = 10:1) to give YQ-025 . 6,7-Dichloroisoquinoline-5,8-dione was prepared by following the known procedure . The following compounds ( YQ-026 , YQ-027 , YQ-028 , YQ-029 , YQ-030 , and YQ-031 ) were prepared by the same procedure for the synthesis of YQ-025 .…”

Section: Methodsmentioning

confidence: 99%

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Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Shin

Jeon

Jung

et al. 2019

ACS Chem. Neurosci.

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Recent clinical approvals of brain imaging radiotracers targeting amyloid-β provided clinicians the tools to detect and confirm Alzheimer's disease pathology without autopsy or biopsy. While current imaging agents are effective in postsymptomatic Alzheimer's patients, there is much room for improvement in earlier diagnosis, hence prompting a need for new and improved amyloid imaging agents. Here we synthesized 41 novel 1,4naphthoquinone derivatives and initially discovered 14 antiamyloidogenic compounds via in vitro amyloid-β aggregation assay; however, qualitative analyses of these compounds produced conflicting results and required further investigation. Follow-up docking and biophysical studies revealed that four of these compounds penetrate the blood-brain barrier, directly bind to amyloid-β aggregates, and enhance fluorescence properties upon interaction. These compounds specifically stain both diffuse and dense-core amyloid-β plaques in brain sections of APP/PS1 double transgenic Alzheimer's mouse models. Our findings suggest 1,4-naphthoquinones as a new scaffold for amyloid-β imaging agents for early stage Alzheimer's.

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Section: ■ Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Shin

Jeon

Jung

et al. 2019

ACS Chem. Neurosci.

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Novel Total Synthesis of Mansouramycin B

et al. 2016

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A novel total synthesis of Mansouramycin B (1) was performed via 10 steps in 28% overall yield starting from the readily available and cheap salicylaldehyde. Two key steps of this total synthesis are noteworthy. The first one is base‐promoted one‐pot aerobic aromatization of N‐tosyltetrahydroisoquinoline 6, the second one is oxidation of 5‐hydroxy‐3‐methyl‐isoquinoline 8 with iodobenzene diacetate [PhI(OAc)2].

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Synthesis and anti-oomycete activity of novel quinazolin- and benzothiazol-6-yloxyacetamides: Potent aza-analogs and five-ring analogs of quinoline fungicides

Beaudegnies

Quaranta

Kessabi

et al. 2016

Bioorganic & Medicinal Chemistry

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Synthesis and antiproliferative activity of new cytotoxic tri- and tetraazabenzo[3,2-a]fluorene-5,6-dione derivatives

Cited by 5 publications

References 11 publications

Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Fluorescent 1,4-Naphthoquinones To Visualize Diffuse and Dense-Core Amyloid Plaques in APP/PS1 Transgenic Mouse Brains

Novel Total Synthesis of Mansouramycin B

Synthesis and anti-oomycete activity of novel quinazolin- and benzothiazol-6-yloxyacetamides: Potent aza-analogs and five-ring analogs of quinoline fungicides

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