A convenient way to dibenzo[c,h]-1,5-naphthyridines (11-aza-benzo[c] phenanthridines)

Bisagni, Émile; Landras, C.; Thirot, Sylvie; Huel, Christiane

doi:10.1016/0040-4020(96)00579-0

Cited by 17 publications

(15 citation statements)

References 13 publications

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“…Synthesis of 1‐methyl‐4‐nitro‐3‐phenylbenzo[e][1,2]thiazine 1‐oxide . It was introduced by nitration of 3 a (0.2 mmol, 51 mg ) with concentrated nitric acid ( 0.4 mmol, 50.4 mg )in acetic acid at temperature below 15 °C.…”

Section: Methodsmentioning

confidence: 99%

Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

et al. 2018

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Section: Methodsmentioning

confidence: 99%

Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

et al. 2018

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“…The synthesis of BENA435 and the related 6-amino substituted dibenzonaphthyridines 4 , 12 , 13 have been already described in Ref. ( 11 ). Additional information on BENA435 and related molecules 1 , 2 , 3 , 5 , 6 , 7 , 8 , 9 , 10 , 11 and 14 is presented in the Supplementary Data.…”

Section: Methodsmentioning

confidence: 99%

BENA435, a new cell-permeant photoactivated green fluorescent DNA probe

Erve

Saoudi²,

Thirot³

et al. 2006

Nucleic Acids Research

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N′-(2,8-Dimethoxy-12-methyl-dibenzo [c,h] [1,5] naphthyridin-6-yl)-N,N-dimethyl-propane-1,3-diamine (BENA435) is a new cell-membrane permeant DNA dye with absorption/emission maxima in complex with DNA at 435 and 484 nm. This new reagent is unrelated to known DNA dyes, and shows a distinct preference to bind double-stranded DNA over RNA. Hydrodynamic studies suggest that BENA435 intercalates between the opposite DNA strands. BENA435 fluoresces much stronger when bound to dA/dT rather than dG/dC homopolymers. We evaluated 14 related dibenzonaphthyridine derivatives and found BENA435 to be superior in its in vivo DNA-binding properties. Molecular modelling was used to develop a model of BENA435 intercalation between base pairs of a DNA helix. BENA435 fluorescence in the nuclei of cells increases upon illumination, suggesting photoactivation. BENA435 represents thus the first known cell-permeant photoactivated DNA-binding dye.

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“…17 Here an alternative, efficient synthesis of dibenzo[ c,h ][1,5]naphthyridinediones is reported in which one of the isoquinolinone nitrogens is substituted with an aminopropyl side chain.…”

mentioning

confidence: 99%

Dibenzo[c,h][1,5]naphthyridinediones as Topoisomerase I Inhibitors: Design, Synthesis, and Biological Evaluation

et al. 2012

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Dibenzo[c,h][1,5]naphthyridinediones were prepared via a novel synthetic pathway. The compounds were designed as topoisomerase I (Top1) inhibitors based on the indenoisoquinoline series of drugs. The results of biological evaluation demonstrate that, unlike very closely related dibenzo[c,h][1,6]naphthyridinediones, dibenzo[c,h][1,5]naphthyridinediones retain the Top1 inhibitory activity of similarly substituted indenoisoquinolines.

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A convenient way to dibenzo[c,h]-1,5-naphthyridines (11-aza-benzo[c] phenanthridines)

Cited by 17 publications

References 13 publications

Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

Ru (II)‐Catalyzed Coupling‐Cyclization of Sulfoximines with alpha‐Carbonyl Sulfoxonium Ylides as an Approach to 1,2‐Benzothiazines

BENA435, a new cell-permeant photoactivated green fluorescent DNA probe

Dibenzo[c,h][1,5]naphthyridinediones as Topoisomerase I Inhibitors: Design, Synthesis, and Biological Evaluation

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